Alas, Poor Villain

""I've seen things you people wouldn't believe. Attack ships on fire off the shoulder of Orion. I've watched c-beams glitter in the dark near the Tannhäuser Gate. All those moments will be lost in time, like... tears... in rain. Time... to die.""

- Roy Batty, Blade Runner

So, there's a villain. Right. Murdering, world-conquering type. The series is ending, so it's time to get rid of him. So he goes out with...a final touching quote and a One-Woman Wail?

As odd as it may seem, if you want the audience to feel sorry for a villain, a good death scene is probably the way to go. This works best if you know their Freudian Excuse; Chaotic Stupid need not apply for this sort of thing. Also works best if this is a supporting villain. We're not supposed to like the Evil Overlord, but we can identify with The Dragon, and especially the Quirky Miniboss Squad, over time and may be sad to see them go. If a Fallen Hero dies, expect everyone to weep openly.

Note that performing one of these incorrectly feels like a cop-out, and usually results in a variation of Karma Houdini. A few well-chosen Last Words are often used to create this feeling.

Compare Cry for the Devil, What a Senseless Waste of Human Life, Antagonist in Mourning, and Death Equals Redemption. See Monster Sob Story when the villain's death isn't required to garner sympathy.

Anime and Manga
"Precia: I never notice things before it's too late."
 * Witchblade with Maria, a cloneblade. After failing to get the Witchblade from Masane, she is stabbed by her. While dying, she sees a hallucination of her biological mother Reina Soho, and asks her "mother" to tell her that she loves her.
 * Battle Angel Alita had Zapan, a bounty hunter cyborg whose problems can all be ultimately traced back to Alita. Exposition time: Alita beat him up and humiliated him for not wanting to serve as cannon fodder for her quest against a brain-eating cyborg. From there, he tries to stop her from helping a wanted fugitive escape, at which point, Alita dupes the security bots on site into thinking that Zapan was trying to steal her proof of bounty. She rips his face off and leaves him for dead, only to be discovered with partial memory loss by a young woman named Sarah who worked at a soup kitchen. The two fall in love, and live fairly happily until Zapan sees Alita on television, gets horrific flashbacks, and has a mental breakdown, screaming "This isn't my face!" as he tears off most of the skin on his face. As he thrashed in pain, he killed several winos, and, more importantly, accidentally decapitated Sarah. He became wanted and horrifically depressed. Alita hunts him down, then, after mind-raping him a second time, she lets him get devoured by cyborg dogs. Almost done: after he's resurrected and put in the super-robot-killing-machine Berserker Body, he starts wreaking havoc on Scrapyard, finally being hit by several 'Collapser' bullets from Alita, and the two are plummeting from several miles in the air, both horrifically wounded and on the verge of death. But suddenly, Zapan wakes up: he's lying on a sleeping mat in the market next to Sarah, who comforts him after he briefly recounts his horrible nightmare. She hugs him and tells him that he's not a monster like the Zapan in the dream is, and that she'll always be with him...and then he snaps out of his mortal-wounding induced hallucination, right back to where he was. He screams Sarah's name once, then continues to disintegrate, but not before flapping his wings just once, enough to break Alita's fall and save her.
 * Magical Girl Lyrical Nanoha A's:
 * The sad fate of a sentient Artifact of Doom, who requested that she be sealed before she caused any more destruction. "Right now, I'm the happiest magical tome in the whole wide world."
 * The movie gives Precia an absolutely heartbreaking death scene. As she falls into an endless abyss, she remembers that Alicia wanted a sister, and realizes that she should have treated Fate as another daughter, and not as a Replacement Goldfish for Alicia, but by then, it's too late for her to make amends or even apologize.

"Ulquiorra: "Do I...scare you, girl?" Orihime: "No. Not anymore.""
 * Also, we might want to add Neon Genesis Evangelion's "I'm sorry... Shinji" to the aforementioned "moving quotes". The Big Bad, Keel Lorenz, got a straight Karma Houdini, unfortunately.
 * Cyborg 009:
 * Sure, there's almost always a Complete Monster amongst the current villains of the week (Often, the doctor controlling them and the Magnificent Bastard, Kane, in the Psychic Assassins), but at the same time, you got the Greek Gods who, other than Artemis, were genuinely unaware of what happened to them before, and many of 'em died in a very horrible way. Atlas and Pan even walked right in to a burning island knowing they wouldn't be able to save Artemis. Minotaur and Poseidon willingly catch fire and die (Achilles wasn't that likable anyways).
 * In the Psychic Assassins arc, Kane is a mix of Complete Monster and Magnificent Bastard, but Lena and her little brother Phil's Heroic Sacrifice more than makes anyone sad. Despite how Mai is shown to be rather cold, she makes a Heel Face Turn but then fades out of existence because the timeline changed and made it so that she didn't exist.
 * Jo's friends from the orphanage became villains of the day, but they all had bombs inside of them. Because they didn't want to kill Jo, they quickly huddled together, said "Bye!" to him, and exploded. The house they lived in caught fire and burned down.
 * The other 00 cyborgs!
 * 0011. He just wants to go back to his family, but after losing to the cyborgs once, his mind gets controlled by Black Ghost, and he dies as a brainwashed machine.
 * 0012. Sure, love did make that odd cyborg crazy, but as the mansion burned down, 004, 007, and 009 spotted her in the window with her husband who never returned to her, who she waited for all these years.
 * 0013...granted he wasn't that much of a villain, but he couldn't take it anymore and jumped off a cliff.
 * 0010+ and 0010- were...rather unlikable, and had almost no redeeming qualities. Until you realize that something wasn't exactly explained and that they possibly made two identical twins into cyborgs who couldn't touch each other...and when the last we see of 0010 is both of them lying on the ground grabbing each other...
 * The 1968 series has one in the second episode. Cyborg X was made to destroy the cyborgs (specifically, 009) by one of Gilmore's ultra rivals. It's actually revealed that he was someone named Naku, and had a girlfriend he left behind, apparently having "died" in a car accident. She was actually willing to kill Cyborg 009 if it meant saving Naku's life, but then she realized that they are both still humans, despite how Naku is under control by the evil Doctor of the week (who is a Complete Monster). Naku, at first, was just carrying out orders to destroy 009, but eventually comes to hate him...so he tried to kill him with an automatic rifle...but his girlfriend pushed 009 out of the way and was killed. Naku released the hostages (003 and 007) and took a cobalt bomb. He said "bye" to everyone and then flied towards Omega, the mad scientist's island. Omega then screamed, "NO WHAT ARE YOU DOING?!" as Cyborg X crashed right into the island...detonating the bomb. Some of the saddest music play, and it's actually quite intense for something made in 1968.
 * The highly Karmic Death of Gargoyle, the Big Bad from Nadia: The Secret of Blue Water, or more accurately, his reaction to it. Instead of quitting with a villainous Big No, he sorrowfully accepts that everything he believed in was wrong and he dies bidding the protagonists farewell.
 * Inu Yasha:
 * Kagura, a member of the Quirky Miniboss Squad, goes the redemption route (sorta) with a final peaceful smile as she dissolves into wind.
 * Jakotsu, who briefly reflects on his second life and tells himself that he has no regrets anymore as he lies in a cave, severely injured. Then, Renkotsu steals his shard and kills him.
 * Kanna, as she joins Kagura in death, leaving Kagome a few final words on how to destroy Naraku.
 * Even Naraku himself when he died lamenting how all he ever wanted was to win Kikyo's heart.
 * Eureka Seven:
 * Ray Beams dies like this, reaching for the wedding ring on her severed arm across the room.
 * Even the resident Big Bad Dewey gets this toward the end, with Holland expressing pity for his brother after the latter's suicide.
 * Miyu's reaction to Alyssa's death at the end of the Searrs arc of My-HiME: "Her beautiful golden light is gone!", followed by an anguished cry of "Why did this have to happen to her?!" and a burial at sea, of sorts.
 * This happens with almost all of the homunculi in the manga of Fullmetal Alchemist:
 * The first time Greed dies, he is somewhat sympathetic and goes out with a "screw you guys". The second time he dies (after he leaves Ling's body to incapacitate Father), he goes out with the realization that, in spite of his possessive personality, all he ever really wanted was friends like Ed and Ling.
 * Gluttony is swallowed by Pride so the latter can gain Gluttony's ability to sniff out his enemies. Gluttony goes out crying and screaming, begging Lust to save him (despite her already being dead), so it's hard not to feel sorry for him.
 * Envy, despite being the worst monster amongst the homunculi, manages to evoke feelings of pity before his death. The jealousy that was used to create him ensures he could only ever despise humans, whom he could emulate but never truly be like.
 * Sloth kind of gets one, going out with a smile. Might be arguable, since he seemed more like a Punch Clock Villain.
 * Wrath goes out with a speech stating how, despite how much he despises humans, their unpredictability made life worth living, and goes out with a smile.
 * Father of all people, in the final chapter/penultimate episode of Brotherhood. As he stands before the Gate, defeated, wondering why God/Truth was unsatisfied, he reveals that all he really wanted was knowledge and the freedom to pursue his own desires like everyone else. Granted, they were not the most commendable of desires, but still, it's kind of hard not to feel bad for him as he's dragged screaming back into the reaches of the Gate, presumably for eternity.
 * In the first anime, most of the homunculi go out like this as well:
 * Lust's death is especially moving, as she has practically switched sides at this point and is about to be finished off by Wrath while she ponders her existence one last time.
 * Gluttony's death in The Movie could almost be considered a Mercy Kill. He loses his purpose for living after Lust's death, and only continues to be a villain because Dante turned him into a mindless killing machine.
 * Greed tells Ed the secret to killing the homunculi before dying by his hand, and says that he is counting on him.
 * A non-homunculus example would be Scar, despite him being more of an anti-villain: he saves Al's life by turning him into the Philosopher's Stone at the cost of his own life. It is very sad, considering that he wanted a genuine relationship with his brother, as revealed in his speech to Lust.
 * Nearly any major death in Naruto. Kishimoto loves emotional death scenes with flashbacks, thus villains and good guys get equal treatment, even when they don't have a case of Redemption Equals Death.
 * Kimimaro and Sasori. And Danzo. And Kisame.
 * Orochimaru got a much more effective send-off in the anime, where viewers were treated to Orochimaru's idealistic beginning and slow and inexorable descent into evil.
 * Kara no Kyoukai has Fujino Asagami, although she's mostly an Anti-Villain. She's been raped, her own father has hired Shiki to kill her, and she's dying a slow, excruciating death via untreated appendicitis. At the end of the episode, she's crawling through rubble, weakly repeating that she doesn't want to die between bouts of vomiting blood.
 * Death Note:
 * After a Villainous Breakdown and, consequently, a failed Hannibal Lecture, Light gets one of the most touching sendoffs ever. In the anime, anyway. In the manga, he begs for his life like the little worm he is. The manga's epilogue chapter ends with a large procession, holding a candle-lit vigil for their dead "savior".
 * In the anime, Misa gets this. Months after Light's death, she puts on her Elegant Gothic Lolita outfit and calmly goes outside for a walk. She reaches the top of a building and sadly stares at the sky... then she closes her eyes, and we see her standing outside the rail...
 * Several of the villains from the anime version of Sailor Moon.
 * First season: Nephrite and Zoisite. The former goes through Redemption Equals Death. In the case of Zoisite, we see him die while telling his lover, Kunzite, how much he loves him.
 * Second season: Prince Diamond, Sapphire, and Emerald. The first two go through Redemption Equals Death, and the third, like Zoisite, stays evil to the end but thinks of the one she loves in her final moments.
 * Fourth season: The Amazon Trio. All three of them go through Redemption Equals Death.
 * Fifth season: Sailor Aluminum Siren and Sailor Lead Crow. Neither go through Redemption Equals Death, but they were arguably never all that evil to begin with.
 * Nakago in Fushigi Yuugi. Throughout the whole series, he does any number of horrible things that make you want him to just freaking get killed already. But literally as he is bleeding to death, out comes the angsty childhood flashback. Turns out, he was an incredibly cute kid who the creepy emperor decided to use as a personal sex slave. This was after he killed his own mother by accident. And by the way? That happened while his mother was being raped. Trauma and cute little kid tears galore.
 * Toguro and Sensui from Yu Yu Hakusho.
 * Master Asia from G Gundam.
 * Treize Khushrenada from Mobile Suit Gundam Wing.
 * Rozen Maiden:
 * In the finale of the first season, Suigintou gets one of these as she slowly dissolves, burns, and essentially asks "Father, why have you forsaken me?"
 * Barasuishou gets one in the finale of the second season, breaking apart in her creator's arms and begging him for help while Jun looks on in horror.
 * Hansel and Gretel from Black Lagoon. Throughout most of the arc, they're depicted as being malicious, cruel, smiling psychopaths. Only it turns out that they were forced to act in horrifying child porn, where they were not only raped repeatedly but also forced to kill other children. Needless to say, it's easy to see why they were so fucked up, and it's easy to at least feel sorry for them. Then, after Balalaika gives Hansel a Shut UP, Hannibal treatment as punishment for harming the subordinates she's so protective of, she orders her men to blow his hand and leg off. When he's lying there, crying and bleeding to death, it's easy to forget that he was a mass murderer. This is taken to further extremes with his sister Gretel, who states that she always wanted to see the ocean and has a heartbreaking Evil Cannot Comprehend Good Does Not Know How to Say Thanks moment when Rock offers her kindness and even sheds tears for her. When they finally reach a seaport and her wish is granted, her brains get blown out by an assassin hired by Hotel Moscow, and she dies saying that the sky and the sea is beautiful.
 * The Anti-Spirals of Tengen Toppa Gurren Lagann spend much of the show's second half brainwashing (and, in The Movie, raping) the hero's girlfriend, programming the moon to crash into the earth, killing most of the hero's companions, and generally trying to inspire as much despair as possible. Their last words? "Make sure...to protect the universe." This, combined with the fact that during the final battle they revealed how much they sacrificed to do so, almost puts them in Anti-Villain territory.
 * The Legend of Zelda Four Swords Plus manga: near the end, Shadow Link is (apparently) dying, and the last words he says shows you that he never wanted to be the bad guy, he just wanted someone he could call a friend.
 * Dragon Ball Z: Vegeta's death after Frieza gives him a No-Holds-Barred Beatdown. Vegeta has been totally despicable for sixty-something episodes, and has just killed a village full of cute alien children and their big brothers. You'd expect a character of this type to die in a spectacular explosion, then never be seen again. But instead, we get a lengthy Final Speech about his genuinely horrendous childhood, and see Vegeta crying as he begs Goku to kill Frieza and avenge their people. Then Frieza gets impatient and shoots him. (Like almost everyone in the series, he gets better.)
 * Bleach:
 * Ulquiorra Cifer, dying right before finally realising what it means to be a human being. His last scene, where he turns and looks at his former captive Orihime, is very sad.

"Yamamoto: Poor thing... Were your emotions taken away from you too? [Stares at Aizen] That was cruel of you."
 * Nnoitra Gilga has a rather different flavor to his Alas Poor Villain than Tia and Stark. With Tia and Stark, the tragedy is that they were both basically good people that were dragged into this war out of a desire to protect their friends, no different than any of the heroes fighting, and their deaths were a pointless waste orchestrated by a man who couldn't give less of a shit about them. Nnoitra could be argued for Complete Monster, but the empathy comes from the defiant but also somewhat pathetic way he faced his end: Nnoitra simply hurls himself at Kenpachi to satisfy his psychotic death wish because he can't stand the idea of living because of another person's mercy.
 * Wonderweiss Margela. Captain-Commander Yamamoto, always cold and stern, expresses pity for the kid when he kills him.

"LA: He wasn't the one who gave me a soul. You were."
 * Even Yammy of all people, gets a certain amount of pathos in the end, as his dog comes and sits next to him and howls. Side materials make this worse, showing that while Yammy was absolutely a stupid, uncaring thug, his simple presence kept the dog alive in the Crapsack World that is Hueco Mundo.
 * Gin Ichimaru. Goes out a la Tousen, although he actually gets to see Rangiku right before he dies.
 * In the X-Cution arc, we have Jackie Tristan. Not only did she have the best Freudian Excuse of the Fullbringers, but in her mix of Better to Die Than Be Killed and Heroic Sacrifice, she tells Renji that she wishes he would've saved her when she needed it.
 * Chrono Crusade gives a large number of the villains this sort of send-off, particularly in the manga version. Rizelle's dying words are asking Aion if she was "any use to you", Genai and Viede die fighting side-by-side with Genai's last words implying that he's going to be by Rizelle's side, Fiore dies (or is frozen in crystal, depending on the version) while trying to protect Joshua, and even Aion has a heart-to-heart chat with Chrono about his motivations—which includes finding out the truth about their mother—before they engage in their final battle.
 * Gantz:
 * Izumi in Gantz is an Ax Crazy Blood Knight who goes on a shooting spree just to be killed and allowed to return to the game. Then, he gets an absolutely awesome death scene where he singlehandedly slaughters twenty-odd vampires sent to kill him and has a touching moment where, in his dying breath, he more or less apologizes to his girlfriend for not paying her the attention she deserves and promises to take her on a date.
 * Nishi's horrible death in the anime. He goes on a lengthy speech of how much he loves and misses his mother before his death.
 * Copy Rezo from the end of Slayers season one. As well as Eris a few episodes earlier. (Both had somewhat less sad deaths in the original novels, though still pitiable.)
 * Harry MacDoogal from Outlaw Star. Yes, he's a villain, and an Ax Crazy Stalker with a Crush at that, but when Hazanko destroys him, Melfina cries out for him, and when he appears as a mechanical "phantom" before Gene and Khan and helps to open the door, he has some poignant final moments.
 * The Tsukumogami girls in Shrine Of The Morning Mist.
 * Beatrice falls in this trope too. She starts the series as a witch who loves to kill Battler's family in the most horrifiyng ways, but in Requiem, we are shown just how Beatrice came to be. And even after she's totally broken, Bernkastel keeps playing with her.
 * Code Geass:
 * In Code Geass Nightmare of Nunnally, Rolo gets one as his body rots away in Anya's arms. After realizing that she was watching over him all the time, he asks whether he, as a Wired, could return to C's world, and she says that she doesn't know. Charles and Marianne manage to accept their deaths relatively calmly compared to the original anime, and Nunnally is clearly saddened by their passing.
 * Lelouch's death, one of the saddest scenes in the series.
 * Rolo's death in the canon series counts as this, Alas, Poor Scrappy, AND Redemption Equals Death.
 * Mikoto from Flame of Recca is considered 'the female Mokuren': smug, bitchy, and monstrous. But then, they both get into a relationship, and while still smug and a monster, Mikoto somewhat mellows a bit. Then, Mokuren conveniently kills her to give him an advantage while she's begging him to stop fighting altogether. Sure, she's done lots of horrible things, but God, she looked so pitiful during her death that the one you wanted to die is not her, but Mokuren.
 * The circus performers of Black Butler. In the chapters after they are slaughtered en masse, they are still shown to be sympathetic characters feeling indebted to a Complete Monster for saving them from life as cripples in a slum, and trying to the save other children at a workhouse. This goes up majorly when it turns out that there were no other children and all of them died for nothing.
 * Madame Red's death was a real Tear Jerker, especially after hearing her backstory.
 * Claymore is quite fond of this trope.
 * Ophelia started gleefully Ax Crazy, got worse, but faced death with dignity and even gratitude.
 * Isley, the Awakened Being responsible for the carnage the Claymores suffered during the Northern Campaign, spent his final moments wishing for just a little more time with Priscilla and Raki, whom he had come to see as his family. It helps that his death is positively horrendous, having spent years running away from a pack of soulless, nigh-indestructible demons and finally being devoured alive by them, bite by bite.
 * Riful of the West frequently treated her lover Dauf like dirt. Yet even after she had lost one arm and one leg and felt the obscenely powerful Priscilla approaching to kill her, she was still unwilling to abandon him (having lost both his legs and one arm) in order to save her own life. Priscilla then proceeded to ram an arm through her and shoot innumerable spikes through her from within.
 * Oh, Christ, and Duph. After he threatens the nigh-godlike Priscilla with evisceration should she harm Riful, Priscilla proceeds to tear out his guts, then murders Riful and leaves Duph to die. What does Duph do? He lets himself get hit by the parasites o' doom that have been shot all over the countryside, turning him into a skull-faced berserking monster that pounds Priscilla into the ground, all while holding Riful's body in one fist. Eventually, he is killed, but not before it's clear how far he was willing to go to avenge the only person he cared about.
 * Kaori Yuki seems to enjoy doing this with her Big Bads.
 * White-Haired Pretty Boy Rosiel from Angel Sanctuary. Because of his legitimate Freudian Excuses (daddy issues, and being Driven to Madness by his Organic Technology), the cast literally crying for the angel seems a bit too much...
 * Alexis from Count Cain. A last-minute reveal shows us that said dead sister is actually the (wo)Man Behind the Man, and has been manipulating Alexis from beyond the grave to drive his family apart and wreck the world...ForTheEvulz. She dies seconds later in a ridiculously over-the-top Death Trap left by Cain. She even mentions that Alexis DID love Cain.
 * The Man Behind the Man of Zambot 3 is this incarnate - a sentient computer core whose entire purpose is to purge evil from the universe. As it dies, it explains that everything it did was in the name of wiping out evil, including humanity, and demands to know why Kappei protected humanity. Upon hearing Kappei's reply, it deems Kappei to be good, and asks him one last, depressing question, "Will the evil-minded people of Earth... ever thank you? Will that planet Earth... ever have that sort of kindness? " before answering its own question, "You are the victor! However... there cannot be any good people on your Earth who are going to thank you!! In this evil-filled Earth... will there even be... one single lifeform... who will appreciate what you did...?" before dying.
 * Cowboy Bebop's twentieth episode featured a mad assassin of Joker likeness named Tongpu, aka Mad Pierrot, who, in the climax, lured Spike into an amusement park to kill him. It's revealed that he was an old man with the mind of a child from inhumane experiments, and when Spike stabbed him in the knee, Pierrot rolled into a ball and cried for his mommy. He then died from having a robotic amusement park animal's foot crush him.
 * This is something of a recurring theme in Cowboy Bebop - basically, any time they successfully track down and kill a mark, it turns out they had a reason for doing what they did.
 * Ghost in the Shell: Stand Alone Complex has this with almost every villain they track down.
 * Notable examples include:
 * The guy who steals a spider-tank as a replacement for his own body which is dying of a progressive degenerative disease, because he wants to visit his mother one last time.
 * The villain from the game, who became a terrorist to protect her dead lover's utopian ideas from commercial exploitation.
 * In the Gungrave anime, this happens to nearly all villains. It would be easier to list who doesn't cause this reaction from the audience. It helps that, despite committing many cruel deeds, most of them are anti villains who have sympathetic motives behind their actions.
 * El Cazador de la Bruja has one for Ellis' creepy and occasionally outright psychotic stalker L.A.. It begins when Rosenburg, who he outright hates at this point and even tries to kill when he meets him, tells him that all the feelings he had for Ellis were fabricated by him, just before brainwashing him into forgetting about Ellis and reverting to cold, ruthless assassin mode, and sending him off to kill Ricardo. One fight scene between them later, he starts to remember Ellis, going into a full-on Villainous Breakdown when Ricardo refuses to let him cut out and meet up with her again. In the end, he gets fatally shot, and starts hallucinating Ellis as the little girl standing over him (who's actually Lirio), realizing, as he dies, that he loved her even before Rosenburg brainwashed him into doing it.


 * In Kekkaishi, the Big Bad, Byakku, is mostly shown as being a completely cold, heartless monster, who sacrifices his own soldiers with mathematical precision, turns people into puppets, and kills anyone who stops being useful to him. The Woman Behind The Man, Hime, we don't see much of, but she at least manages to come across as callous, seemingly sending her armies against the Kekkaishi's Protectorate on a selfish whim. In their interactions with each other, Hime is a Spoiled Brat drama queen, and Byakku is as icy as ever. At the end, however, their entire dimension is collapsing, and as the heroes make their escape, Byakku - previously killed by an old enemy - gets better, and, rather than flee, rushes to the side of his rapidly-weakening princess. With stoic calmness, he fulfills her final wishes (even though she wonders why he isn't saving himself), as the fortress-like dimension briefly returns to its original appearance - an endless, golden wheat-field. They share a tender moment, reflecting on what's really important, before the dimension collapses around them, reducing them both to nothingness.
 * Hellsing gives us Rip Van Winkle, an evil Nazi vampire and huntress. She starts panicking when Alucard gets within fifteen miles of the ship she's on. After that she's curled up in a ball crying. When Alucard shows up, she spends most of the fight in abject terror, and stops crying only long enough to shoot Alucard. That works about as well as could be expected, and he slowly impales her with her own musket, giving the viewer about three minutes of rape imagery while he slowly drinks the blood that has spilled out onto the deck, using ten extra arms growing from his back to hold her still and basically grope her. Then he finally puts her out of her misery...by biting into her neck with his mouth full of sharp teeth and sucking her dry, followed by him absorbing her. Her commander watches her over a satellite video link, congratulates her, and opts to give her a "hunter's death" instead of flipping the remote kill switch. This scene is often cited when discussing whether Alucard is an Anti-Hero or a Villain Protagonist.
 * Also notable is that she's the only Millennium agent that doesn't boast how their going to kill Alucard. She knows how dangerous Alucard is and does her best to get away, but Alucard hunts her down.
 * Kuruku from Unico in the Island of Magic fits this trope quite well, given both his backstory and the "kill'em with kindness" death he suffers.
 * Even though he was an unrepentant murderous rapist, Shira's death in Blade of the Immortal was so gruesome and horrifying that any hint of satisfaction the audience may have felt promptly evaporated. That he uses his dying breath to tell Renzo not to follow in his footsteps probably had something to do with it as well. There is, of course, a distinct possibility that he was merely messing with him, but still...
 * Heartcatch Pretty Cure gives us Dark Pretty Cure. She spends most of the series as a stoic Evil Counterpart who seems to exist only to dog Yuri and provide a strong opponent for the Cures once in a while. Then episode 47 reveals that she just wants to cement her place as Sabaaku's real daughter, having been made to replace Yuri. Then episode 48 gives us her death scene proper, where Sabaaku comforts his now-badly-injured "other daughter" and refers to her as Yuri's sister. The vulnerability coming from the heretofore borderline-emotionless Dark as she is embraced by Sabaaku and fades away makes it even more saddening.
 * Blue Submarine No. 6 has Dr. Zorndyke. who explains that after losing his wife and child, the world seemed wrong, and he set about changing it, before ripping out his own heart. And Verg too, if he did die at the end.
 * Suitengu Choji seems like a power hungry, money obsessed Magnificent Bastard in Speed Grapher, but near the end of the series, his backstory is revealed, turning him into a more sympathetic villain. Everything he had done in the anime was for revenge, against the people who had destroyed him and against the society that had allowed it. Just before the end, he spares his blind and helpless enemy, and then spends his last moments with his most faithful servant.
 * The Nothing Card in the second movie of Cardcaptor Sakura, a Woobie, Destroyer of Worlds. She had a sympathetic backstory, imprisoned alone beneath Clow Reed's house to act as a sponge for the negative energy the Clow Cards created. She escaped when Clow Reed's house was demolished and systematically stole the cards from Sakura Kinomoto as well as erasing parts of her hometown. Sakura managed to convince the Nothing to perform a Heel Face Turn.
 * In Mirai Nikki, virtually of the Future Diary owners receive this trope although Yukiteru Amano and Kamado Ueshita may be excused and others have take their own Heel Face Turn. Most notably are Yuno Gasai who suffered a terrible childhood, went insane and became a god in order to repeat time to respend her days with her loved one Yuki, until she eventually is Driven to Suicide to ensure he becomes a god. She gets better though.
 * Then we have Tsubaki Kasugano, the local Woobie, Destroyer of Worlds who went totally mad after years of orphanhood and sex slavery. The manga had her angrily and despairedly scream as her Tragic Keepsake is used in her death, but the anime makes her look more sad than angry...
 * This is rare and far between in a work such as Berserk where every villain who has been presented and killed off totally deserved what was coming to them. Except one: Rosine. Poor Rosine grew up in an abusive household and used the myths about the elves in a nearby valley as her only refuge. One day she couldn't take the abuse any longer and decided to run away to the valley in order to make her dreams come true, but unfortunately, she would learn that there were no such things as elves, making her reach her breaking point which in turn allowed her to  She intended to make a paradise with the minions that she created, but it was anything but. Then Guts comes and brutally and relentlessly hunts Rosine and  . As she lay dying, it was revealed to her that there were such things as elves, but she just wasn't one of them, making her regret   and then tries to return home to them, but   It's made even more sad in that

Comic Books
"Edgar Jacobi: Heh. Well, you know that kind of cancer that you get better from eventually? Rorschach: Yes. Edgar Jacobi: Well, that ain't the kind of cancer I got."
 * Lord Zarak (A.K.A. Scorponok)'s death in The Transformers. This could seem to not count, since he was trying to stop Unicron, and therefore not dying in a villainous way, but remember that he was the Decepticon leader at that point.
 * Moloch in Watchmen. It was made more poignant because, on many levels, it had more to do with Rorschach than him. Not to mention this part:

"Obi-Wan: I thought you'd use your dying breath to curse us. Asajj: Perhaps I have...or perhaps I just...hate Dooku more than I hate you....Or maybe...you were right about me...all along...."
 * Mr. Hyde in The League of Extraordinary Gentlemen singing "You Should See Me Dance the Polka" as he jaunts off toward the tripod is particularly emotional when it hits you that, for all his unbridled depravity, you'll never experience his brilliantly dark humor again. Throw in his unrequited love for Mina, and it gets exponentially more difficult to read.
 * It's also a bit difficult not to feel bad for Moriarty, given the horrifying manner of his death.
 * Asajj Ventress from the Clone Wars series. She is given sympathetic qualities in the middle of the series, and her journey to woobiedom is completed at the very end when her hero and mentor, Count Dooku, orders her shot to death because he can't be bothered to wait for her. She makes one last pitiful attempt to kill her nemesis, Obi-Wan Kenobi, and is cut down by Anakin. As she lays dying, she reaches out for Obi-Wan and tells him to watch the Galactic Core and Coruscant. Her final words finally reach Alas, Poor Villain territory:

"Lady Jaye: You fight somebody long enough, you get to know them... and after awhile-- you start to respect them."
 * Then, it's subverted when the medical ship that her body was placed aboard mysteriously vanishes, and it's revealed that, terrible though her wounds were, it takes more than that to bring her down.
 * When Destro was thought to have died in Marvel's G.I. Joe series, Snake-Eyes and Scarlett lay flowers at the place where he supposedly died.

Fan Fiction

 * Though rare, it is not unheard of for this to happen with Voldemort in Harry Potter fanfic. One such fanfic used a spell to make Voldemort revert back to the boy he was before he became evil (hand waving the fact that in canon, young Mr. Riddle was pretty much screwed from the beginning), and then Harry held him and comforted him while the shock of all the terrible things he had done slowly killed him.
 * Pretty thoroughly invoked in Go Not Gently...somehow.
 * Of all the villain deaths in Ponies Make War, the only one that earns any audience sympathy is Empyrean. He's only a villain because Titan forces him to, and isn't even all that good at it. His mini-Villainous Breakdown when the Mane Six break into his throne room and strip him of his power is pathetic, and it's hard not to feel sorry for him when Titan shows up, decides he's useless without his powers, and kills him while he begs his father for mercy.

Film
""I don't deserve this. To die like this. I was building a house." "Deserve's got nothing to do with it.""
 * King Kong is the Trope Codifier.
 * Davy Jones in Pirates of the Caribbean. Barbossa, too, but to a lesser extent, as Barbossa didn't have a Freudian Excuse, and in any case, he got better.
 * But...but...Barbossa didn't even get to eat the apple before dying in the first movie! *Baaaw* He was a much straighter example, at any rate, in the first movie, but less so in the sequels, because, as was mentioned above, he got better.
 * Subverted by in the fourth film by Blackbeard, however. He's given the perfect chance to have such a moment by sacrificing his own life to save his poisoned daughter, but instead elects to Kick the Dog and save his own life instead. He ultimately dies anyway after Jack pulls a Poisoned Chalice Switcheroo.
 * The title character of Kill Bill goes out much like this when the Bride finally takes her revenge.
 * Dr. Octopus in Spider-Man 2. "I will not die a monster!" Also, Norman Osborn/Green Goblin from the first movie. "Peter...don't tell Harry..."
 * "You got me, Charlie. What are you gonna do now?"
 * Hook gets this in his last moments, when he's struggling to get back on the ship while the Lost Children bully him into falling in the Croc's maw.
 * The American dub of Godzilla 1985 has Raymond Burr reflecting on how this trope applies to Godzilla.
 * In Godzilla vs. Destoroyah, it's played again, this time far more successfully. By now, he's a bit of an Anti-Hero, though.
 * The oft-maligned American version also has a strong influence of this at the end.
 * It goes all the way back to the original 1954 film in which we see that Godzilla is a Tragic Villain, and is as much a victim of the atomic bomb as everyone else. It makes his death at the end all the more heart-wrenching.
 * In The Lion King 2, Nuka, The Unfavorite, mostly just wants his mother to appreciate him. In the end, he dies trying to get her attention and fails even at that. He spends his last breath apologizing to Zira for failing, his death prompting one of the only displays of love and affection that Zira probably ever showed him.
 * Gollum from The Lord of the Rings.
 * Taken even further in the book, as Frodo refuses to be upset with Gollum for what he did - even saying that without him, the whole Quest would have failed.
 * Kadaj from Final Fantasy VII Advent Children. His death scene was a surprisingly effective a Tear Jerker for some.
 * In The Mummy Returns, Imhotep is abandoned by Anack-su-namun—for whom he essentially damned himself in the first place—as he is desperately clinging to a ledge. For a moment, he can only stare at the O'Connells—Evie having just rescued her true love, Rick, from the same situation—with a look of absolute, crushing despair. Then, with nothing left to live for, he lets go of the ledge and allows what looks like the souls of the damned to drag him into the precipice.
 * The novelization takes it even further. Rick, despite himself, actually tries to save Imhotep from falling into the abyss. Imhotep still lets go of the ledge, but not without a few parting words acknowledging that Evie and Rick's love for each other was the real deal.
 * The death of Roy Batty, leader of the rogue replicants, in Blade Runner. From his Tannhauser Gate death speech: "All those... moments will be lost in time, like tears... in rain. Time ...to die." And one dove rises.
 * Lady Deathstrike from X-Men United definitely got such a send-off. Especially since her death was so painful looking and because she was Brainwashed and Crazy at the time. Stupid Stryker.
 * She almost certainly wasn't evil. At one point, her eyes return to their normal (brown), non-brainwashed colour, and she looks around confused, clearly unaware of where she is. Stryker casually walks over to her, jerks her head forward, and applies the mind control serum to the hole at the base of her neck. She remains under control for the remainder of the film, with her eyes only returning to normal in the midst of her death scene.
 * Khan from Star Trek II the Wrath of Khan. It is absolutely tragic that a man who could've been so many other things was reduced to being so owned and blinded by hate that he was willing to die just to see Kirk die with him.
 * He couldn't even come up with his own quote.
 * That's because Khan was savvy enough to know where all the best stuff is.
 * And yet he said that "Revenge is a dish best served cold." was a Klingon proverb. (A) how did he know about Klingons? and (B) why not just say Sicilian when we all know it that way?
 * The Penguin in Batman Returns. Even though he was a hideous psychotic sewer-dwelling monster, in his last few moments, he comes off as quite pitiable, and his burial at sea by his own beloved penguins actually comes across as rather moving. It should've been Narm, but it somehow worked.
 * "Shit...I picked the cute one." The scene is really an effective use of Bathos using humor to accentuate the sadness.
 * What makes it really sad is that he spent the whole movie angry that he wasn't accepted. And it turns out he was.
 * Ironically subverted in Hitchcock's Strangers on a Train. Foe Yay Magnificent Bastard Bruno is dying, and for a second it seems like he is going to admit his guilt; instead, he uses his last breath to further accuse the protagonist in front of the cops.
 * The Villain Protagonist/Antagonist in In Bruges, who wanted to kill the other lead character for accidentally shooting a choir boy in a hit on a corrupt priest. Sure, he's a hitman, but as he says for his final words..."You've got to stick to your principles." Why were those his last words? While chasing the lead through a parade route, he shoots the lead in the heart. However, the bullet goes through the lead and hits the lead's midget friend. Due to the type of bullet that the antagonist was using, the midget's head was completely destroyed. The midget was also wearing full pageboy uniform due to his part in a film, so naturally, the antagonist thinks that he has shot a young child in the head. He sticks his gun in his mouth, but the lead is unable to talk the antagonist out of taking his own life (largely due to the antagonist having repeatedly shot him in the chest), and he says that line just before he shoots himself in the head. However, despite the morose nature, it isn't very tear-jerky, just depressing and humanizing.
 * The eponymous character of Blacula. After watching his beloved Tina - the reincarnation of a woman he's waited centuries to see again - get staked through the heart, he deliberately walks out into the sunshine, killing himself.
 * Dr. Frank N. Furter's last song, I'm Going Home, and subsequent death is an example of this in the Rocky Horror Picture Show.
 * Robert Webber manages to turn his last scene in The Silencers into one of these.
 * Hilariously subverted in Motel Hell.
 * More of an "Alas Poor Mook" but in Jurassic Park III, one can't help but pity mercenary Cooper, who tearfully pleads for the plane to stop for him as the Spinosaurus approaches.
 * Those poor hunters who were hired by Mr. Ludlow in The Lost World: Jurassic Park. All of them dead, by either T-Rex or raptor jaws and claws, and many of their families now suddenly deprived of their source of income.
 * William Foster in Falling Down. "I'm the bad guy?"
 * Little Bill in Unforgiven.

""You came back. A man like you? Why?""
 * Calvera in The Magnificent Seven goes out trying desperately to understand why. Of course, much of the pathos comes from Eli Wallach being just that good.

""Guy gets on the MTA in L.A., dies...think anyone'll notice?""
 * The death of Riley Biers in Eclipse. In his final moments, he calls out for his lover, Victoria, only for her to ignore him.
 * Darth Vader's death is probably one of the most famous examples of this trope.
 * The Rancor from Return of the Jedi. A dancing girl and a guard already had the misfortune of being its lunch. Luke has to work hard to avoid being torn apart by this hulking beast, and the spectators are very surprised when he manages to kill it. Then a fat, ugly man dashes out and cries as if Luke has just killed his pet puppy, and he's led away, weeping inconsolably. It's such an unexpected and well-played reactionthat it was no longer just our hero slaying the dragon. Even this ravenous monster had someone who cared for it, and probably cared in return.
 * This inspired writers in the Star Wars Expanded Universe to expand on this, turning the Rancor in a Tragic Monster that was another victim of Jabba the Hutt's cruelty. It did have good relationship with the fat guy, who was its trainer, and the reason why it ate most anything that was thrown into its pit was that it wasn't fed very often. Jabba also forced it to take part in a number brutal fights against other dangerous creatures, and in fact before Luke came he planned to have it face off against Greater Krayt dragon, something even bigger than it was. The trainer had plans of escape for him and the Rancor, but Luke happened to show up...
 * In Revenge of the Sith Viceroy Gunray was cornered by newly christened Darth Vader, when he pleaded that the Separatist want peace he was cut down mid sentence.
 * HAL 9000 in 2001: A Space Odyssey. Despite being an apparently cold, logical computer AI who was willing to murder the crew of Discovery One, it becomes apparent why he did so: He was afraid. He did not want to be reprogrammed for making an error, which would essentially kill him. In the end, he is lobotomised while pleading for his life with the sole survivor (David Bowman), who ignores him. "Stop, Dave. I'm afraid. I am afraid, Dave. Dave... My mind is going. I can feel it. I can feel it..."
 * The Stephen King movie Sleepwalkers looks like it's building to this, with the titular soul-sucking cat monsters constantly stalked by theor weakness, and they're possibly the last of their kind. The young male Sleepwalker reads poetry describing their plight in class and seems to be falling for the female lead. A redemption plot looks all but guaranteed... And then when he tries to eat her soul, all the drama around whether or not he's falling for her vanishes and he becomes a gleeful Complete Monster with shocking speed.
 * Vincent from Collateral.


 * Both halves of the Big Bad Duumvirate from The World Is Not Enough.
 * Gen. Francis X. Hummel from The Rock. The fact that he was actually an Anti-Villain makes you feel even more sorry for him when he dies.
 * Sadako Yamamura, the Designated Villain from The Ring series, suffers a lot even before she becomes a villain. She is raped in the novels, lost her mother in both continuties, beaten to death by angry actors, and then she bonded with her evil twin and kills all those who harmed her before, including her own innocent boyfriend, before being tossed down the well by her stepfather.
 * In Ring 2, Sadako appears before Mai Takano and Yoichi Asakawa as a ghost, asking why they can escape the well and yet she cannot, before allowing herself to fall back down into the well for eternity.
 * Samara Morgan, the American version of Sadako, suffers a lot too and is thrown down a well by her adoptive mother. This doesn't help, since her biological mother tried to drown her as a baby. And then she gets trapped in the well again at the hands of Naomi Watts.
 * In The Faculty, Casey kills the alien queen, Marybeth. As she is dying, he softly tells her, "You wouldn't have liked it here anyway.", acknowledging that—despite being a monstrous parasitic alien—she was just another outcast trying to find her place.
 * In Law Abiding Citizen, Aimes participated in a burglary. The plan appeared to be that his partner, Darby, would knock the adult occupants of the home to the floor with a baseball bat, then Aimes would handcuff them and then throw valuables from the home into a bag. Darby kills two people during the burglary while Aimes watches in horror and protests. Due to some legal technicalities and deals, Darby gets off easy while Aimes is executed. Aimes' last words: "What I did that day was wrong. But I'm not the one who killed those people. You're executing the wrong guy."
 * Wolf Boss in Western Animation//KungFuPanda2 carries out Shen's plan without much mercy, but his death (stabbed by  for refusing to fire his own men) is really saddening.

Literature
"Martel: You always said I'd come to a bad end, little mother, but you were wrong. This isn't so bad at all. It's almost like a formal deathbed. I get to depart in the presence of the only two people I've ever really loved. Will you bless me, little mother?"
 * Count Olaf from A Series of Unfortunate Events, one of the few cases where it works for the main villain.
 * Severus Snape in Harry Potter. Yes, he did have his reasons, but we didn't know that at that point in the story, and it was still a sad scene.
 * Peter Pettigrew as well. He was unrepentant about what he did, but the way he died and the reason he died (strangled by his own magical hand for sparing Harry's life) makes it seem like it was more than he deserved.
 * Grand Admiral Thrawn from The Thrawn Trilogy. "But it was so artistically done..." As the first major Imperial who was ruthless and pragmatic but not outright evil, he was always a fascinating character. Even his enemies couldn't help but admire him - an X-wing jockey once said, "I'd like to meet him, shake his hand. And then kill him, of course" - and his underlings adored him. Since he was killed in the same trilogy where he first appeared, other books involving him either have the New Republic freaking out over his possible return or are set earlier - and the earlier they are set, the more ambiguous they are about how much of a bad guy he really was.
 * The first book of the Inheritance Cycle ends with the main character seeing the memories of the Shade he killed in the finale, revealing how he came to be how he is.
 * Nearly every book in the Redwall series uses this trope, and half the time, it's the Big Bad!
 * Martel's death in David Eddings' The Elenium fits the bill. After three books of playing Worthy Opponent to Sparhawk, he admits he knew Sparhawk was better all along, and both Sparhawk and Sephrenia forgive him and give him their blessings. Just for a minute, the guy who betrayed the entire Pandion Order goes back to being Sparhawk's brother in arms again.

"She shuddered. "She tortured me — yet I pity her.""
 * Similarly, Zedar's fate in The Belgariad makes one almost feel sorry for the guy. Sealed up in the ground, forever? Yeesh.
 * Worse when you consider that his Face Heel Turn was a result of being forcibly turned by the Big Bad, and not of his own volition.
 * Speaking of which, said Big Bad also gets an Alas Poor Villain. Torak was a God of Evil, a Narcissist, and an utter bastard, but his death at the end, screaming for his mother as burning tears pour of his eyes after Garion takes away everything that matters to him? It's not pretty and it's acknowledged in-universe as such. The same could be said for Asharak, whose awful death will likely haunt Garion for the rest of his life.
 * There's a retroactive example in The Malloreon. Taur Urgas, King of Cthol Murgos was a frothing madman, and was played as such in the The Belgariad. In The Malloreon he comes off even worse as we find out what life in his home was like for his children. Garion notes when talking about the terminally-depressed 'Zakath that he would much rather be fighting Taur Urgas ("now there was a man I could cheerfully have gone to war with. He polluted the world just by living in it.") And then Eriond points out that "he was insane, Garion, and that's not his fault." At that point, all of Urgit's comments about his father's fits of madness and irrationality come back to you in a whole different light, as you realise that the man was genuinely clinically insane, and not merely Axe Crazy, and never got any help for it.
 * Warrior Cats has a tendency to do this with most of its villains, due to its Gray and Gray Morality policy.
 * Most notable for Tigerstar, at least in the first series. Firestar notes afterwards that he could have been a great and noble warrior if he hadn't let ambition control him. Not to mention the truly horrible death he suffered: being ripped open, and subsequently bleeding to death NINE TIMES.
 * The reader might not feel this way, but Rafen from James Swallow's Warhammer 40,000 Blood Angels novels feels some sorrow when he sees the corpse of Sachiel.
 * A nice Foil to Sachiel's gloating over Rafen's (presumed) death.
 * From Codex Alera, for all the horror she had caused, all the death and the near destruction of the world, the Vord Queen seems, in the end, to be a sad, lonely child seeking the approval of her father.
 * Cao Cao of Romance of the Three Kingdoms gets a long poem on his death, daring anyone to criticize him.
 * Smug Snake Yuan Shu dies as a result of some mixture of illness, starvation, and dehydration, all the result of his last botched campaign. His last words are a request for a little honey water for his throat, to which his chef replies that there is no water in the camp, save that which is tainted by blood.
 * Many villains from Memory, Sorrow, and Thorn by Tad Williams get this treatment.
 * King Elias, despite playing the Unwitting Pawn and being a complete Jerkass throughout most of the series, reveals that all the evil he commits (and abets) started with grief over his wife's untimely death. At the very end, he begs to be killed so he won't become the host for the Eldritch Abomination that the Big Bad Storm King has become.
 * Fengbald, the viciously amoral leader of Elias' army and the man Princess Miriamele was going to be forcibly married to, dies pitiably when he's caught in the trap of the Fake Defectors at the battle of the Stone of Farewell.
 * Ineluki, the Big Bad himself, is revealed to have committed all the atrocities in his life out of love for his people and a desperate desire to lead them to salvation. In the end, this realization leads directly to his defeat.
 * Utuk'ku, the Norn Queen and The Chessmaster behind Ineluki's rise, is broken by the failure of the Evil Plan, and is left as nothing more than what she always feared to become: a frail old woman.
 * In Otherland, Tad Williams' next offering, the death of Corrupt Corporate Executive Felix Jongleur is suitably karmic as his creation, the Other, turns his worst fears against him. However, given the glimpses we're allowed to see of his upbringing in a Boarding School of Horrors and how his entire adult life has been driven by fear of the Anthropomorphic Personification of Death, it's hard not to feel sympathy for the poor tormented kid who grew up to be a bully himself, but died screaming in absolute terror.
 * A Dragonlance universe short story has Tanis and Flint kill a Black Mage who's been sucking the life out of people. After he's dead, they find out that he was doing it to prolong the life of his sickly son.
 * Test of the Twins: the Archmage Raistlin Majere attempted to become a god by dethroning one of the current ones. He manipulated everyone around him, abandoning or killing them as soon as they stopped being useful, and, as shown in an alternate would, have not only succeeding but have DESTROYED every other god in the pantheon, leaving him sole ruler of the universe. However, he sacrificed himself to save his time-traveling brother, ex-friend, and one of the people he manipulated, because they showed him that he would destroy the world in the process of attaining godhood.
 * Several villainous characters by John C. Wright are pitiable when they die:
 * War of the Dreaming: Angelo Casselo, who knows he's nothing but a pawn in the game; and Manannan, alias Tom, a What Measure Is a Non-Human? who had been desperately playing both sides in an attempt to prevent his people being annihilated.
 * Chronicles of Chaos: Grendel Glum, who, for all his monstrousness, is merely a lonely old man, and Echidna, who is killed in the middle of her Mama Bear rampage.
 * Brandin in Tigana. And he's the main villain too.
 * Steadholder Mueller at the end of Ashes of Victory, simply because he was an Unwitting Pawn.
 * Almost every half-blood villain in Percy Jackson and The Olympians gets this in the final book. Luke tries to kill the heroes multiple times and tries to help the Big Bad, Kronos, rise again (eventually hosting him in his own body). In the final chapters of The Last Olympian, he sees Annabeth bleeding, breaks free from Kronos's mind control, and realizes that he was fighting for the wrong side. He then kills himself to destroy Kronos, and it is indicated that he goes to Elysium in the afterlife. Ethan Nakamura fights in a battle to the death against Percy, and when Percy wins, he refuses to kill Ethan. Ethan repays him for this by betraying him and pledging himself to Kronos, enabling Kronos to rise again. Throughout The Last Olympian, he is seen working for the Titans. Then, Percy convinces him to turn against Luke/Kronos, who kills him, earning him sympathy in the end. Silena Beauregard originally seems like a gentle, romantic daughter of Aphrodite. However, she is secretly a spy for Luke, and the information she has reported has lead to the deaths of many campers. When Kronos and his minions become responsible for the death of her boyfriend, she begins to think twice about her actions and eventually disguises herself as Clarisse, rallies the absentee Ares campers, and charges a Drakon, resulting in her death. Her secret - that she was the spy - comes out as she is dying, but the other campers remember her as a hero anyway.
 * The Phantom of the Opera—Erik's death has this effect both on readers and on his fellow characters.
 * In Robert E. Howard's Conan the Barbarian story "The Slithering Shadow", Thalis tortures Natala, but after the titular shadow swallows her up:

"Olivia closed her eyes. This was no longer battle, but butchery, frantic, bloody, impelled by an hysteria of fury and hate, in which culminated the sufferings of battle, massacre, torture, and fear-ridden, thirst-maddened, hunger-haunted flight. Though Olivia knew that Shah Amurath deserved no mercy or pity from any living creature, yet she closed her eyes and pressed her hands over her ears, to shut out the sight of that dripping sword that rose and fell with the sound of a butcher's cleaver, and the gurgling cries that dwindled away and ceased."
 * In "Shadows in The Moonlight"—Shah Amurath

""I have a cat, you know. Back home. [...] She doesn't have a name. She is just Cat. She curls up on my chest whenever I sit down, and goes to sleep. I hope she doesn't miss me. I'm going to miss her.""
 * In Dracula, Renfield's death invokes this trope. He's mostly unsympathetic for most of the novel—he nearly beats a man to death and attacks one of the protagonists with a knife—but when he realizes that Dracula had lied to him, he attempts to defend Mina Harker from him and is fatally injured because of it. The graphic description of his injuries doesn't help.
 * In Skulduggery Pleasant: Mortal Coil, the death of the Russian assassin Tesseract. After being fatally injured by Lord Vile, Tesseract removes his mask and asks Skulduggery to help him get outside so that he can feel the sun on his face one last time. As they go, he talks about how he'll miss his cat, and how he has no regrets.

"'Wait,' she said, her voice weak and somehow very young. She didn't look like a mad faerie sorceress now. She looked like a frightened girl. 'Wait. You don't understand. I just wanted it to stop. Wanted the hurting to stop.' I smoothed a bloodied lock of hair from her eyes and felt very tired as I said, 'The only people who never hurt are dead.' The light died out of her eyes, her breath slowing. She whispered, barely audible, 'I don't understand.' I answered, 'I don't either.' A tear slid from her eye and mixed with the blood. Then she died."
 * Mandrake is introduced in Duncton Wood three chapters in as a bloodthirsty, giant mole that later becomes an iron-fisted dictator. Then, in a quick moment of Rebbecca's life, he scolds her for enjoying the snow and, after that, delivers a speech against the snow that's quite pungent considering his story. And when he finally dies, he does so half-mad from wandering the Ancient System for months alone, crying for his only daughter while being mercilessly beaten down by a revengeful Stonecrop.
 * Sly Moorcock from Stark by Ben Elton is a ruthless billionaire who has no qualms about leaving Earth with the other billionaires and letting humanity die in the inevitable ecological breadown. Yet he moves more and more into Anti-Villain territory as the story progresses, and shows himself in possession of both moral standards and the capacity to love, and when he commits suicide in the epilogue by throwing himself out of an airlock, it is just as sad as when one of the good guys die.
 * In Azure Bonds, the red great wyrm dragon Mistinarperadnacles lays down her life to destroy the Darkbringer Moander. The heroes mourn her, and one of them, Akabar, notes that Mist's evil was fairly petty while she died saving the world from A Fate Worse Than Death. He even suggests that the group's bard should compose a song about her.
 * Aurora in The Dresden Files, the well-meaning but insane villain of Summer Knight

"Faquarl: Your discovery is remarkable. But it comes too late for me."
 * In Good Omens, the demon Duke Ligur is doused in holy water in a booby trap set up by Crowley. He thoroughly deserved it, but for a demon, it's an amazingly horrible way to die, and his partner-in-crime Hastur immediately goes into Villainous Breakdown and attempts a Roaring Rampage of Revenge on Crowley, chasing him down a phone line.
 * Phoena's death in Fusion Fire was so horrific that Brennen did his best to comfort her in her last moments, despite the fact that not only was she responsible for his capture by the Shuhr, but she also tried to have him and his wife essentially tortured to death.
 * The third Safehold book, By Heresies Distressed, has this happen with Prince Hektor of Corisande. He's been beaten, he knows it, and he is preparing to negotiate terms of surrender with Emperor Cayleb. Before he can, however, he and his eldest son and heir are victim of an assassination that is blamed on Cayleb. Hektor, in his final moments, realizes that he truly loved his son, who had thus far been The Unfavorite.
 * In The Bartimaeus Trilogy, Faquarl achieves the vengeance he's been craving for 5000 years, and discovers that it doesn't bring him the satisfaction he wanted. Then he finds Bartimaeus sharing a body with a human, proving him wrong about the inevitability of conflict between humans and spirits. Bartimaeus narrates that he's never sure if, had he wanted to, Faquarl couldn't have killed them before they shot him.


 * In Death: this has happened with some of the murderers after they get caught or killed. Portrait In Death has Eve and Peabody realizing that the murderer they caught wasn't greedy, vicious, or downright evil, just pathetic.
 * Time Scout's Skeeter Jackson truly feels sorry for what happens to the enraged gladiator who spent the entirety of Wagers of Sin trying to kill Skeeter.
 * Antrax in The Voyage of the Jerle Shannara was just following its programming. Its reaction as it slowly loses contact with the outside world and shuts down is as sad as it is necessary.
 * The Aeneid: Most of the antagonists go out rather sadly. The standout may well be Mezentius, Nay Theist, exiled tyrant, and brutal fighter whose disdain for the gods and vicious rule over his old city-state have brought him to Italy to fight as a mercenary. When his son and Morality Pet Lausus is slain, Mezentius goes ballistic, cutting down opponents left, right, and centre before being stopped by Aeneas; his Famous Last Words, wherein he refuses to pray and asks only that he buried by his son, are quite touching.
 * Durza, the Shade from Eragon, surprisingly earns sympathy just before his death at the hands of the protagonist. While fighting off the Shade's mental attacks, Eragon accidentally breaks through into his mind and sees a quick succession of images from his early life, before he became a Shade. The man who became Durza was originally a young orphan named Carsaib who was taken in by a sorcerer and instructed in the art. When his master was murdered, the grief-stricken young man called upon powerful spirits to get revenge, but they proved more than he was capable of handling and possessed him. Durza was pure evil, but Carsaib was a tragic figure who made a terrible mistake and paid dearly for it.

Live Action TV
""I did my duty for Queen and Country. I did my duty for Queen and Country. I did my duty for Queen and Country.""
 * From Doctor Who, The Master. Repeatedly.
 * Also, that one Dalek, from the episode of the same name. Never has the word "Exterminate" been uttered with such pathos.
 * Oh man, that poor Krafayis from "Vincent and the Doctor", an invisible alien that kills a child in its first "appearance". Who gets the blame? Vincent. And yet, later, after Vincent manages to fatally stab it with his easel, we find out that this particular Krafayis was actually blind, and its supposed "attacks" were just fearful acts of self-defense, having been abandoned and left all alone on Earth by its pack (according to Eleven, it even gasps out "I'm afraid" repeatedly in its last moments). The Doctor realizes this as it's dying and tries to soothe it, even though he can't even see it. Cue tears.
 * Not sure if Cybermen count as villains rather than mind-controlled Mooks, but if they do... "Why am I cold?"
 * Yvonne Hartman, upon her final scene as one of the Cybermen, fighting off all the other ones.

"Doctor (translating the Minotaur's grunts): "an ancient creature drenched in bloodshed" (...) "for such a creature, death would be a gift.""
 * The Minotaur in The God Complex. Spent the whole episode "feeding" on the fears of those trapped in the hotel, but at the end, was revealed to be just another.

"Caligula: And what makes you think that a filthy smelly old woman like you could become a goddess?"
 * Angel's villains go out this way from time to time, which is natural for a show that swims in the Grey area. Nearly all the major antagonists get taken out this way, and it's up to the viewer to decide whether or not their fates were just. Darla, Lindsey, and Lilah each had ridiculously sad and depressing death scenes, while Holtz and Jasmine began to show signs of this trope, but would then yank it away by either setting into motion their own death or by tossing Angel off a bridge and then kissing him to screw with Connor, respectively.
 * Holland Manners, as well. Sure, he was rather unrepetant in his actions, and his role in manipulating Angel led to a particularly Karmic Death, but Angel's leaving him to plead for his life, about to be torn apart by Darla and Drusilla, was treated by Wesley, Gunn, Cordelia, and the audience as a stepping stone in our main character's Moral Event Horizon.
 * Livia, the Evil Matriarch of I, Claudius was so pitiable on her deathbed that even Claudius, who knew her murderous nature well, was touched. Caligula on the other hand...

"Stan: (Crying) C-can we go around one more time? Vincent: I don't think so. Stan: I-I wish you were my dad. Vincent: (Last words) Forgive me."
 * Caligula himself died a rather pitiable death. It must be quite a shock to discover that you are not immortal after all.
 * All the villains of I, Claudius qualify: Tiberius dies asking for lamb cutlets, Messalina frantically begs the soldiers sent to kill her not to take her head, and Sejanus (possibly the most despicable villain in the whole series) asks what has become of his children (both dead, and his daughter raped first because it was against Roman law to execute a virgin).
 * Criminal Minds: poor, poor Vincent Rowlings. Made even more heartwrenching by his last dialogue with his Morality Pet:

"Logan: Beaver, don't! Cassidy: My name is CASSIDY! Logan: Cassidy, don't. Cassidy: Why not? [Logan can't say anything] Cassidy: That's what I thought. [He jumps]"
 * Cassidy from Veronica Mars was very pitiable when he killed himself. Freudian Excuse came into play massively.

"McCoy: I wish we hadn't had to do this. Kirk: So do I. They gave us so much. The Greek civilization, much of our culture and philosophy came from a worship of those beings. In a way, they began the Golden Age. Would it have hurt us, I wonder... just to have gathered a few laurel leaves?"
 * Star Trek: Deep Space Nine: Weyoun. Yes, he dies several times. But a few of his deaths are very poignant, and very much ARE this trope. Particularly
 * After his final death, the Female Changeling breaks her usual Fantastic Racism to mournfully acknowledge him as "the only solid I ever trusted."
 * Star Trek: The Original Series had a few of these (in keeping with its avoidance of actually evil villains). One was Apollo (yes, that Apollo), who spent the episode trying to coerce and cajole the landing party into worshipping him so he could suivive, all to no avail because Kirk and co. have Outgrown Such Silly Superstitions and so, he fades away in a moment of Woobie-ness...

"Jiiya: "Master!" Tsurugi: "Hey, Jiiya?" Jiiya: "What is it?" Tsurugi: "Is it okay for me to dream?" Jiiya: "Yes! Don't worry about anything. Jiiya will always be by your side." Tsurugi: "Thank you, Jiiya.""
 * Another was Dr. Richard Daystrom, whose Motive Rant about being laughed at behind his back and underestimated is legitimately heartbreaking. The fact that Daystrom is portrayed by William Marshall - an amazingly talented black actor who was undoubtedly kept out of roles by racism - adds an excruciating Reality Subtext.
 * The Wire has two examples of this: Stringer Bell in Season Three and Bodie in Season Four.
 * Dollhouse has a prime example of this in one of its final episodes, when Boyd is wiped, strapped up with explosives, and sent in doll state to destroy Rossum HQ. The doll stock line "I try to be my best" clinches it.
 * The villain of Harper's Island, Henry Dunn, is Impaled with Extreme Prejudice by the protagonist Abby Mills, the girl he's in love with. OK, that love is creepy and unwanted, but he goes out professing his love for her.
 * He's a certainly a lot less antagonistic than the other villains in the series, but Sano/Imperer's death in Kamen Rider Ryuki is no less heartbreaking. In summary, Sano had finally attained a semblance of the happiness he'd always wanted, only to be betrayed by a man he thought was his friend and left to dissolve in the Mirror World with no hope of returning home. "I only wanted to be happy", indeed.
 * In Kamen Rider Kabuto, we get the Rich Idiot With No Day Job Tsurugi, who has thoroughly become a lovable comic relief character...until it's discovered he's really the Scorpio Worm. The real Tsurugi's over-the-top personality had over-riden the Worm's, essentially Becoming the Mask. While it seems like Tsurugi has betrayed humanity, even his potential love interest, it's actually all a part of a gambit to lead the Worms to ruin by following his orders. And it succeeds. Every Worm is defeated. Every. Worm.


 * Lost: The Man In Black. Once you learn his tragic backstory and motive, you can't help but feel sorry for the guy.
 * Captain Sawyer of Horatio Hornblower. Cruel towards his lieutenants and especially Midshipman Wellard, unstable, and antagonistic, but you can't help but pity the man who used to be a hero of the Nile. His death comes as both a relief and a tear jerker, especially as, directly beforehand, he had momentarily regained a shred of sanity, and he and Wellard had faced the escaped Spanish prisoners together with dignity.
 * No matter what you thought of Shane Vendrell after he murdered Lem in Season 5 of The Shield, you can't help but feel sorry for him when he killed himself (and his family) in the series finale.
 * NCIS: in-universe example: Ari. Ziva is clearly affected by killing him, she sings a song over his body and is haunted by it. Justified, they are half-siblings. The fans, of course, probably did not feel the same way.
 * Power Rangers Lost Galaxy: Scorpius was a creepy looking Galactic Conqueror, but he genuinely loved his daughter, and his formal deathbed, with her in attendance, is quite sad. The deaths of Noble Demons Loyax and Villimax also tugged at some heartstrings.
 * Queen Beryl in Pretty Guardian Sailor Moon. The real motivation behind her attempt at awakening Metaria and ruling over the world? She wanted to get back at Princess Serenity who always had everything she dreamed of: fame, beauty, power, and, most of all, Prince Endymion's love. 'Why do you... take everything away from me?'
 * Breaking Bad has an interesting subversion. The twins go out in a particularly inhumane fashion and are still treated as the irredeemably evil force they have been up until that point, but that scene served as the climax to an episode that opened with a flashback to their Freudian Excuse.
 * Played straight, however, with Hector and (arguably) Gus in the next season.
 * Nick Cutner in Being Human (UK). Especially after the flashbacks. He was just desperate for approval from people who treated him so horribly, including Hal. In the scene where the Old Ones utterly cut him down his down his devastation is heartbreaking. Then he gets cooked.

Multiple Media

 * Makuta Krika in Bionicle; he was the Noble Demon of the Makuta with a Monster Sob Story, who only went along with the plan of the Makuta of Metru Nui because he saw it as a "damned if you do, damned if you don't" scenario. He made a genuine effort to help the Toa (the heroes) at the end of the Karda Nui arc, and then, when he learned that the Makuta were about to outlive their usefulness, he tried to warn them, and was rewarded by slowly becoming so intangible that all of his atoms flew apart - the kicker of his death was that it was caused by his own power being forced out of control by his brethren, who thought he was lying.

Theater

 * Subverted in Oklahoma!. Curly tells Jud that when he dies, people will cry for him despite being afraid of him prior to his death. When he actually dies, what's the first song that they sing? "Oh what a beautiful morning..."
 * Tybalt. After all, the hero had just murdered him for what had ultimately been an accident.
 * Of course, as this is Shakespeare, the validity of this is really up to the director and the actor. Paris would also be a good example. He's often displayed in a negative light, but ultimately, is simply a man trying to woo a girl he's in love with in the typical fashion of that era, and he's killed while trying to arrest a dangerous criminal who had killed the cousin of the woman he loved, and, for all he knew, drove her to suicide.
 * Javert from Les Misérables gets sent off with an absolute Tear Jerker of a song, after having his entire worldview shattered.

Video Games
"Sora: You're...you're Fading! Axel: That's what happens when you put your whole being into an attack...not that Nobodies actually HAVE beings, right? Hehahahaha..."
 * Although Durandal from Marathon is not technically a villain, he is forcing people to die meaninglessly, and sends the player on suicide missions, sometimes for the hell of it. Tycho also reveals that he doesn't care about humanity or the S'pht (in fact, he might hate humanity), he just wants to find the Eleventh Clan of the S'pht because he believes that they know where he can find the Jjaro, who have the ability to help Durandal become God in the next universe. Nevertheless, he did want to stop the Pfhor invasion of Earth, and killing him was a horrible thing to do. Until, of course, we find out that he wasn't really dead.
 * Most of the bosses in the Metal Gear Solid series gets this, including Psycho Mantis, Vulcan Raven, Sniper Wolf, Fortune, The End and even Vamp.
 * Solidus's defeat was also somewhat pitiful on his part: He ended up killed by the Patriots via Raiden, after working hard to re-establish America as how the Founding Fathers founded it with liberty, especially when he literally had nothing else to leave behind other than this. This is best demonstrated by his final actions: After falling from Federal Hall, his last visible action is him reaching up to a statue of George Washington in longing, as he attempted to redo America the way Washington originally founded it.
 * The kicker though, has to be every single member of the Beauty and the Beast unit from number 4. And if their respective backstories didn't solidify their position as the official Woobies of the game, their death scenes, where their humanity finally shows through, are a pretty good litmus test for deciding if there is an ounce of humanity in you.
 * No sympathy for Zero? Yes, he's the cause of the events of the series (albeit indirectly, it's hard to be responsible for the actions of your AI constructs when you've been brain-dead for most of their reign), but he truly meant well and it just didn't go right. By the time we see him in 4, he's a pitiful old vegetable who can't even take responsibility for the things he didn't know he caused.
 * The Quirky Miniboss Squad from MGS is even more this trope for a lot of people who've read The Last Days of Foxhound. Sure, it may not be canon, but it does a damn good job of characterising them all in a sympathetic manner, even Liquid himself.
 * The Boss' killing. Until a minute later, you really feel this. After that, whatever humanity there was just gets strained as you learn the truth. Considering how well it was done, it may still be a poor villain because of how well the boss played her roll.
 * Godot's defeat in Phoenix Wright: Ace Attorney: Trials and Tribulations could count.
 * Acro's defeat as well, with his remark (that you have to interpret for Regina) about how he wanted to stick around. He's worried that he might be in prison or executed by the time his brother gets out of his coma.
 * Axel from Kingdom Hearts. The fact that he jokes about his death makes it worse.

"Vexen: "I don't want to...go yet..." Lexaeus: "Forgive me, Zexion..." Demyx: "No waaaaaaay! *Sob!*" Luxord: "How could you...Roxas?" Larxene: "I'm...fading? No, this isn't...the way I...I won't ALLOW...!""
 * Even Saix gets a pretty touching sendoff. "Kingdom Hearts... where... is my heart?." Indeed, nearly all of the members of Organization XIII get touching sendoffs (save for Xemnas, Xigbar, and Xaldin), which is one reason why they get the Draco in Leather Pants treatment.

"Riku Replica: So this is the end... figures. But I'm not afraid. Good riddance to an artificial life. I've never had a real heart. Even what I'm feeling now is probably fake. Riku: What are you feeling? Riku Replica: What happens when someone who's not real dies? Where will my heart go? That is, if it doesn't...disappear completely... Riku: It'll go somewhere. Probably the same place my heart will go. Riku Replica: Heh...how original...oh well..."
 * And it's not just the Organization. A certain Artificial Human got a heartbreaking farewell...

"Roxas: Did I... do this to you?"
 * And now we have the death of Xion. As if the events leading up weren't wrenching enough, then comes the Ret-Gone...

"Illusive Man: There...Earth. I wish you could see it like I do, Shepard. It's so...perfect..."
 * Vanitas' death might be the most impressive example of this in the whole series—in spite of being literally made of darkness, the expression he makes right before he dies is so lost and sad that it's hard not to feel bad for him. It doesn't help that his face is identical to Sora's, apart from the eye and hair color.
 * The Fire Emblem series in general is quite fond of this trope. More specifically:
 * In Fire Emblem 8, a vast majority of fans were bawling at the death of Lyon, quite possibly the most likable main villain in the history of the game. Mostly because he wasn't the villain...
 * The cool, ambitious, suave, and incredibly likable (despite many Kick the Dog moments) General Caellach. It was plot essential to kill him, which would have been more saddening if he wasn't That One Boss...
 * Also from Fire Emblem 8: Selena—the good general hopelessly in love with her dead King.
 * Let's not forget that Fire Emblem 6 has Gale, who was never your enemy, and was possibly romantically linked to one of your party members (though it isn't necessary to kill him) and Brenya in the bonus chapters - fighting for a king already dead and knowing she only fights to be killed to stall your army. Hell, the final boss was a frail looking girl, though she gets better.
 * From Fire Emblem 7: Black Fang member Linus, or Lloyd if you managed to get the alternative chapter.
 * Heck, pretty much all the major Black Fang members. Brendan, Uhai, Ursula, Darin, and yes, even Nergal himself, whose death becomes more pitiable depending on how many bonus chapters you unlock. Pretty much the only Fang members you can completely hate at the end of the day are Psycho for Hire Jerme, Church Militant Kenneth, Evil Matriarch Sonia, and Complete Monster Ephidel, who probably has the most satisfying demise in the game.
 * Some people felt that Sonia was broken a bit too much, invoking Sympathy for the Devil.
 * And Kenneth and Jerme might earn a modicum of pity as well when you consider their appearance as Morphs in the finale chapter, Go Out with a Smile included. It is implied by Eliwood and Co. that both men were driven insane by Nergal, especially when you consider that Jerme used to be the Fang's finest assasin before Jaffar joined the Four Fangs - Brendan had already shown he didn't tolerate sociopaths by locking up Pascal Gretzner (who deserves to be on the list of 'completely hateable Fang members') in the past, after the man massacred innocents while gunning for his targets, just because he enjoyed killing so much.
 * Another is Nergal's top lieutenant, Limstella. Despite being a rather creepy, emotionless Artificial Human, she has an absolutely gut-wrenching final moment: "I am not human. This body and this heart are constructs. Yes, as is this sorrow."
 * Back in Fire Emblem: Seisen no Keifu, several people Tear Jerked over Alvis, who was actually similar to Lyon, and wasn't entirely the evil bastard he would appear to be if you took him in context. (One Freudian Excuse later) Heck, he was actually shown to be attempting to stop the Child Hunts that were going on. Even Celice, whose father was murdered by Alvis, later says that Alvis does not deserve to be demonized in history.
 * Even earlier were Camus and Emperor Hardin in the Akaneia series. The former is a Honorable Knight who helps the player at several points even though he works for the enemy and suffered from My Country, Right or Wrong. His death is somewhat lessened by Gaiden revealing that he was Not Quite Dead, but he still gave up his old identity as Camus. The latter was a trustworthy ally who fought alongside Marth, and was a great Hero to the many he rescued from slavery. He ended up going through a Despair Event Horizon and getting Brainwashed and Crazy into being a power hungry tyrant. As he's dying, he reverts back to his old heroic self. Both characters likely inspired the later tragic villains in the series.
 * The remake of the game adds Kleine. Throughout the game, she's depicted as a sadistic, cold-hearted killer, who constantly abuses her adoptive sister Katarina for being useless. So, of course, you look foward to the moment when you finally get to fight her...and her death comes as one of the most heart-wrenching tear jerkers in the series, specially when she asks Katarina "Stay with Me Until I Die".
 * Also, Eremiya from the remake. She seems to be a Complete Monster throughout all her appearances, is the one to blame for Kleine being the way she is (and Katarina, and Roro, and Roro's clones...), then when you finally beat the bitch, it's like a moment to celebra - what's this?! Gharnef put her under Mind Rape when she fell into despair after witnessing the deaths of the orphans she originally cared for during the war, turning her into a Mega-Abusive-Bitch? And now, while she's dying, he completely restores her memories of who she once was, laughs, and lets her bleed to death in complete despair? ...Ouch. Just...ouch! For a character who didn't even exist in the original game, that's some pretty powerful Jerkass Woobie material right there, gosh. Damn that Gharnef - there's a very good reason he earns more loathing than the game's actual Big Bad, Medeus.
 * Let's not forget General Zelgius (Levail as well, for that matter) in Fire Emblem Radiant Dawn. Yes, Zelgius is the Black Knight who killed Greil, but you still can't help but feel sorry for the guy.
 * Then there's his boss,, a Woobie, Destroyer of Worlds and Death Seeker who's out to end it all because he can't see the good in the world anymore. The latter's cohort, Dheginsea is another example, as is Jarod, who for a relentlessly unpleasant Jerkass gets a surprisingly sympathetic send off, going down fighting after giving a Rousing Speech to his troops. The previous game has Antivillains Shiharam and General Bryce, whose death's cross the line into Player Punch territory, and Petrine who while an incredibly vicious bitch for most of the game, goes out so terrified that it's hard not to at least pity her.
 * Optionally, Hetzel might get one. Of all the Begnion Senators, he's clearly the least evil. (eg, buying Rafiel as a slave only to save him and then release him.) Even when you do fight him, he apologizes and says he doesn't want to do it, he's more afraid of what Lekain will do to him if he doesn't go along with it. Data that has been found suggests that he could have been spared, actually.
 * Grom Hellscream in Warcraft. Despite slaughtering his way across two entire planets, despite embracing demonic corruption twice over, despite condemning his people, and despite frequently jeopdardising the future of the Horde...his Heroic Sacrifice and death scene in Reign of Chaos makes up for it. Almost.
 * The final moments of Arthas Menethil in World of Warcraft surprisingly fit this. Despite constantly hearing that nothing remains of Arthas himself, there's still enough for him to cling to his father's specter in search of some final comfort as he lies dying. Somewhat eclipsed by the ensuing Heroic Sacrifice.
 * Given Illidan's official Woobie status throughout much of Warcraft lore, his death (by betrayal, no less) at the end of the Black Temple raid dungeon is tragically empty. What a Senseless Waste of Human Life indeed.
 * Baldur's Gate's Irenicus is rather pitiable in his final moments. Even more so is.
 * Valkyria Chronicles' Selvaria blew herself up with most of Gallia's army, but the look on her face and her reasons for doing so will just make you feel sorry for her.
 * Maximilian. Its clear that the writers intended for him to be sympathetic in his final moments.
 * Aribeth in Neverwinter Nights, if you can't turn her back. All of the other villains in that story and the expansions are of the Ax Crazy variety, though.
 * Darth Malak in Knights of the Old Republic. Despite setting up camp on the far side of the Moral Event Horizon, his doubt and regret as he's dying is just believable enough to earn a little sympathy. Bastila, too, if you decide to kill her (or have to because you can't talk her down, although less so there.)
 * Only if you take the Light Side choice. If he dies in the Dark Side choice, he just mutters that you are eviler than him, and he just doesn't measure up.
 * Many villains in the sequel - Colonel Tobin, Darth Sion, Atris, Kreia...well, maybe not Nilhius.
 * One of the original ones for Video Games was Oddler/Odd Eye in Shining Force II. Dude joined you as a blind kid with no memories, he follows you and clearly admires your skill, and stays behind with Creed. Unfortunately, he turns out to be a greater devil and is fought as a boss, wishing, as he died, that he could live his life again not as a devil.
 * After each of the mind-blowingly epic boss battles in Shadow of the Colossus, you are treated to a brief cutscene of the colossus succumbing to death accompanied by remorseful and heartbreaking background music. Surely enough, you feel like a sick, twisted bastard for killing such a magnificent creature.
 * They're not even villainous. They are only antagonists because Wander made a deal with Dormin to save Mono. They wouldn't be bothering anyone if you weren't there.
 * Hell, Phalanx, the Thirteenth Colossus, doesn't bother anyone even after you try to kill it- It is fleeing from you the entire time. You son of a bitch.
 * In Mass Effect, this applies to Saren if you manage to convince him to shoot himself; he goes out whispering the words "Goodbye, Shepard. Thank you."
 * Matriarch Benezia, as well, particularly since she started out trying to keep Saren from going too far and ended up Brainwashed and Crazy for her efforts.
 * In the sequel, the Collector General, when it's revealed that Harbinger has been possessing it all along. The way it looked around in confusion and reaches up at the hologram of Harbinger (because it is literally all it has), as the space station was blowing up around it just tears your heart out.
 * Although it's uncertain when, exactly, he fell, at the final moments of Mass Effect 3 you're confronted with an indoctrinated Illusive Man. He can either be made to realise this, in which case he shoots himself with a resigned, "I tried, Shepard", or he can be gunned down, following which he looks out, one last time, at the view of Earth and comments;

"Mithos: Farewell, my shadow, you who stand at the end of the path I chose not to follow."
 * The supposed Luna VI that was actually an illicit AI called Hannibal gets one of these when you destroy the last of its mainframes. Sure, it had killed or was trying to kill everyone around it, but when you pull the plug the terminal fills with binary code that, if translated in real life, reveals the word "help" repeated over and over. Hannibal is scared of dying and, basically, is desperately shouting "Help me!" over and over as he fades away.
 * This is made even sadder by the revelation that.
 * All of the God-Generals save Dist, who survives, in Tales of the Abyss get one of these. After the speeches they give about their ideals before their final fights (most of which involve copious amounts of angst), it really makes you feel like a douche for having to kill them. Of course, there's some Gray and Grey Morality in there, given some of them...
 * Arietta's might be the worst, however. She's one of the least malevolent of the God-Generals and has, at that point in the game, lost everything that matters to her...and unlike the other God-Generals, who mostly get fought in Boss Battles and then die off afterwards in cutscenes, she actually does die directly due to the player beating on her. And she's only a little girl!
 * Sync tends to get this the least out of the other God generals (Sans Dist, since he never actually dies), mostly because he didn't seem to give as much of a shit about it all. Yeah, he's got some angst and all...but he psychologically tortures Anise and does all sorts of things that almost push on the Moral Event Horizon.
 * The game also does this to Grand Maestro Mohs.
 * On the subject of a Tales of game, Tales of Phantasia also has one of these. Which was the game's primary twist in the end, since Dhaos had stated in the very end that he didn't want to be ultimately confronted by the heroes since he was just trying to save his people. Even the characters say that they appear to be the bad guys from Dherris Karlan's point of view. Way to go, Cress.
 * Alice in Tales of Symphonia: Dawn of the New World. Most people absolutely despised her after all of the cruel things she did, treating Decus like crap when he is in love with her. After their final fight, Decus even takes Emil's sword for her and died in Alice's arms. She realized that she loves Decus after all, proceeded to go into an Unstoppable Rage to avenge his death. Not to mention that she even cried for him. Then, she said that soon they'd be together again and held his hand as she died.
 * This is following after a few Pet the Dog moments from her, too.
 * Heck, even the first Tales of Symphonia had this with either Zelos (if you got the 'bad' ending), who pulled a Face Heel Turn (in his last words, he's talking about how his death might make life easier for his estranged sister), or Mithos himself, who started this entire 'chosen' and got involved in the 'splitting the world/harnessing mana' mess because he wanted to bring his sister back from the dead. His last words don't help.

"Kefka: Why create when it will only be destroyed? Why cling to life, knowing that you have to die? None of it will have meant anything once you do. Terra: We live to protect what we hold dear. As long as you have that, you can find the meaning on your own. Kefka: Meaning, schmeaning. The whole world's going bye-bye! You included! Life... Dreams... Hope... Where do they come from, and where do they go? None of that junk is enough to fulfill your hearts! Destruction... Destruction is what makes life worth living! Destroy! Destroy! Destroy! LET'S DESTROY EVERYTHING!" *explosion, followed by a sobbing laugh*"
 * Poor Walter in Tales of Legendia. He was just doing what he was conditioned to do since birth.
 * One really couldn't help but feel sorry for Lambda after hearing all of the stuff that was done to him by Emeraude. Almost makes you feel glad for him when he blows her up.
 * Caster in Fate Stay Night's "Unlimited Blade Works" scenario. Yes, she captures and tortures Saber, holds Taiga hostage, and is responsible for many a Bad End in Unlimited Blade Works, including one where she orders Shiro's friend, Issei, to kill him. Yet her last moments were so touching, it almost made you forget all that...
 * Kirei Kotomine in "Heaven's Feel", even more so. Considering that the only thing he finds enjoyable and lives for is to cause pain and suffering, and is apparently trying to destroy the world For the Evulz, when they get to his backstory, you can actually feel quite a bit of sympathy for the guy. Even Shirou admits that he kind of likes Kotomine in that route. But anyway, he tried to be a good person and finally decided that he was going to bring the devil into the world and see if maybe he could get some answers for why his morality was broken.
 * Zouken Matou.
 * Ilya, who in 'Fate' was a psychopathic monster at worst and The Scrappy at best, appeared in 'Unlimited Blade Works' long enough for a Tearjerking finale with backstory that managed to Woobify her without even giving away her whole Freudian Excuse (which was saved for 'Heaven's Feel'). And Beserker, already Deader Than Dead from his Self-Destructive Charge, managed to stand long enough to give her comfort before both died.
 * Baten Kaitos Origins does this for almost every villain in the game, with the exception of the game's biggest Complete Monster and the one who was pretty much horror incarnate. This is particularly notable in the case of the Big Bad and his Dragon, both of whom had their daughters crying over their bodies as they died, but it also shows up in the deaths of the rest of the Five-Bad Band - such as Nasca, who fought despite knowing it was practically suicide simply because "Heughes would never let me live it down!" Then you get to Heughes...who does the same thing because running away would be a bad example to set for Nasca.
 * Final Fantasy has this from time to time:
 * Kefka, of all people, gets this in Dissidia Final Fantasy.

"Revas: You know what? It doesn't fucking matter anyway. [Looks down the shaft with an expression of fear] Just don't forget me... [Lets go]"
 * The end of Final Fantasy IX had Kuja dying at the base of the Iifa Tree. Being a fluke with a crushingly short life-span made him cruel and nihilistic, but only when he was defeated by the heroes and had nothing left to live for did he realize too late what it means to really live. This also gets a callback in Dissidia.
 * Final Fantasy XII: despite their eventual descent into madness, Cid and Vayne have some redeeming qualities, and even Venat manages to garner some sympathy:
 * Vayne is one of the most affable and - dare one say it - likeable antagonists in the series due to the inherent humanity behind his actions, and though he does Kick the Dog on occasion, he's a Well-Intentioned Extremist par excellence with good emphasis on the "Well-Intentioned" part of that description. His genuine love and compassion for his cute little brother Larsa helps immensely.
 * In the case of Cid, it hits especially hard when the player realizes that Cid only started neglecting his family because Venat contacted him.
 * Venat exemplifies all the best aspects of the Satan Is Good trope - the compassionate Defector From Decadence to contrast with the Jerkass Gods, the genuine liking for mortals and a desire for them to attain self-independence (much like Prometheus), and the capacity for kindness when s/he sacrifices his/her immortality simply so that Vayne doesn't have to die alone; as such, they depart the world together and in some semblance of peace.
 * Final Fantasy Tactics: Wiegraf Folles and his sister Milleuda, who both started off well-intentioned and were arguably more heroic than the heroes during Chapter One. Of course, Wiegraf eventually went too far, what with joining the Corrupt Church and selling his soul to the Lucavi, but still...Milleuda, in contrast, was sympathetic until the end - being forced to kill her to progress in the game is a notorious Player Punch.
 * Isilud Tengille, who wasn't even evil - when he realised he was on the wrong side, he tried to stop his father-turned-demon, only to be unceremoniously killed, followed by asking Ramza's sister Alma to send Ramza his apologies for having opposed him.
 * Both Confessor Zalmour Lucianada and High Confessor Marcel Funerbis had incomplete information, and seemed to genuinely believe they were doing the right thing. Zalmour goes out with a commendable dignity as he prays to God - not the Lucavi demons - to punish the wicked for their sins, and Funerbis swallows his pride as he begs Ramza "the Heretic" to stop the demons (after having been run through by the Big Bad and his minions despite pleading for his life).
 * The main (human) antagonist of Xenogears  vowed to use science to create a God to replace the one who had created, and then abandoned, the world. In despair over the death of his unrequited love, Sophia, he succeeded in bringing "God" back to the world in the form of a malevolent alien superweapon. Upon its destruction and his own defeat, he was taken up directly to Heaven by the true God, while telling the reincarnation of Sophia and her lover that he envies their capacity for unsullied human love.
 * The main antagonist of Xenosaga exhibits this trope as well. After commenting positively about the fact that he will no longer have to fear losing anyone (a fear which was the catalyst for his decent into psychopathy to begin with) in oblivion, he tells the protagonist, whom he has known since childhood and who is clearly distraught by the climax of their encounter: "What's with that face? You look like... you just lost your best friend." The protagonist himself is on his knees crying at this point, and you should be too. Ironically, he cries out for the antagonist not to 'leave him alone', a sentiment the antagonist exhibited in childhood upon realizing that he was immortal and would outlive the people in his life.
 * BioShock (series). the Big Daddies. After you kill one, its Little Sister runs up to the corpse, crying and asking for it to get back up again.
 * The Alpha series, those bastards who attacked with no warning. You're going to feel like a true Heel when you learn the reason why they're so suicidal. They lost their Little Sister, who was literally their whole world. Later, you're treated to the fact that one of them spent the remainder of his life crying next to a Gatherer's Garden. Almost makes you want to kill them just to put them out of their misery.
 * What about Andrew Ryan? He can DEFINITELY be considered a villain, with the whole trying to kill you bit, but his death is too jaw dropping for words. And with you realizing he was always free and you never had been, "A man chooses, a slave obeys. OBEY!" Think about it, he ASKS you to kill him!!
 * Skint in The Reconstruction. Towards the end of the story, it seems like he's going to turn out to be the Big Bad, but when your party arrives at The Very Definitely Final Dungeon, you find him collapsed in a bloody heap right outside it. He reveals that he actually tried to stop the Big Bad and was on the heroes' side the whole time before asking Dehl to Mercy Kill him.
 * Interestingly, Cave Story doesn't do this for the Big Bad, but for the little guys. In the standard ending, the cutscene features a slow pan over the various levels of the game and all the enemies in them, set to sad music. Then, the floating island they're on crashes.
 * Also, Misery, except in the perfect ending.
 * Invoked in-game in Super Robot Wars Original Generations, as part of the Retcon given to Axel Almer. Originally, in the face of death, he continued to mock Lamia and died 'being a doll on his own will'. In the remake, however, after his heartfelt confession on how the Artificial Human surpassed his very low expectations, he mutters Lemon's name before his demise, signifying his genuine care; even Raul, who was practically angry at Axel, who caused Fiona to disappear, feels bad on having to kill him. Then, it's subverted in Original Generation Gaiden, when Axel comes Back from the Dead and has a Heel Face Turn.
 * An even better example is Echidna Iisaki, one of Lamia's sisters. Thought to be personality-less as the W Numbers are suppose to be, in the end, she's revealed to be completely sentient when she disobeys orders to come back alive at all costs in order to take a fatal blow for her Mistress's boyfriend, Axel. When asked why, she responds that it would make her Mistress sad if Axel was killed, as, while she can be replaced as many times as needed, humans are gone when they die. Lamia begs her to eject so they can help her, but the dying Echidna defiantly proclaims "I am not... Echidna Iisaki! I... am... W16...". Axel's reaction on both occassions counts for this trope. While the original had him cursing over how a doll he hated saved his life, you feel sorry for Echidna dying and still being treated like trash by her superiors; the remake had Axel lamenting over how her death will end up demoralizing the whole Shadow Mirror army.
 * Kitaniji from The World Ends With You fits this well. He, upon realising he has failed to save Shibuya, leaves it in Neku's hands, accepting his fate for Shibuya's sake.
 * Walter Sullivan, of Silent Hill 4. Spends the first half of the game brutally murdering everyone the player character meets and the second half trying to kill him while laughing hysterically, but it is still almost impossible to hate someone whose final action was to desperately call for his mother.
 * Dark Knight Andoras in Tactics Ogre. All of 'em pretty much were jerks, sans Lans Tartare, Volaq (due to being Out of Focus, but what little we do see paint him as an honorable man), and maybe Ozma in the remake. But then comes Andoras, who actually joins Barbas and Martym in betraying the other three, possibly for personal gain. So you'd probably think he was dislikable, like Barbas and Martym were. But he actually did it because his family and countrymen were enslaved by Lodis, and he wanted to get back at Lodis to free the countrymen he felt were "hostages". Before he dies, he even warns Denam that Valeria must be united, because that was the reason that the Bolmarkians (his nationality/ethnicity) and Nirdums (the Royal family he was a part of) fell to Lodis.
 * In the Gaiden Game, Rictor and Cybil come off this way. Shaher also only wanted attention from God, too.
 * For that matter, a lot of bosses give lines when they die, such as characters lamenting about how they couldn't give medicine to their sick daughter, how the boss was fighting for his wife, and how the wife of said boss was pregnant...Matsuno really wanted to drive home the point of how war affects everybody in terrible ways.
 * In Dragon Age Origins, the moment when (if) Teyrn Loghain is executed is one of these, as his daughter weeps and begs for his life and he looks back saying that little girls never grow up and always have pigtails in their hair. Then she gets spattered with her own father's blood.
 * Iji's final boss, General Tor, gets a death scene like this.
 * Doctor Breen in Half-Life 2, who genuinely believes that what he's doing is the only way that humanity can survive. His Evil Gloating and attempts at Not So Different get increasingly desperate as Gordon gets closer and closer, and right before his death, he tearfully cries "You need me!"
 * Genbu from Tenchu 2 died on his feet and with a smile on his face.
 * No More Heroes often invokes this with the deaths of each boss, many of them being sympathetic and all of them being awesome. Good examples include Dr Peace, Holly Summers, Jeane, Ryuji, and Captain Vladimir.
 * Alice Twilight certainly qualifies. By the time Travis meets her, she's sunk into depression, mourning the loss of Margaret Moonlight who she had some connection to, and honestly just wanted to die. She even basically spells it out to Travis that the reason most of the assasins he's encountered have been so delighted to meet him is because they all just want to be freed of the endless fighting. It's also her death that causes Travis to have a Villainous Breakdown/What The Hell, Hero moment as he finally gets sick and tired of the killing.
 * Thomas and George from Deadly Premonition. Thomas secretly had a crush on George, and was jealous of Emily over the fact that George obviously cared for her. This jealousy was used by Forrest Kaysen to drive him murderously insane, forcing Emily to kill him. As for George...you wouldn't think he'd get a touching sendoff, given his actions, but then you realize that he only did the murders because the horrific Cold-Blooded Torture his own mother subjected him to during his childhood deeply traumatized him to the point that he wanted to become strong above all else. Oh, and like Thomas, he was essentially being used by Kaysen.
 * George's pitiableness is driven home during his Villainous Breakdown, where he tearfully calls out to his long dead mother, saying that it wasn't his fault and begging her to not to hurt him again...
 * Ganon, oddly and impossibly enough, manages to invoke a tiny bit of sympathy with his death in The Legend of Zelda the Wind Waker. The wind is blowing indeed.
 * In The Legend of Zelda Twilight Princess, Link and Zelda also express pity as Ganondorf passes away, though that seems to just make him hate them all the more.
 * Not to mention the fact that his death blow is actually done by Zant, who was his servant and clearly turned on him, likely killing them both.
 * The final rank mission of San d'Oria in Final Fantasy XI ends with this trope. With Prince Trion aiding your party in the fight, the head of the Orcish tribes, Warlord Rojgnoj, falls at your feet. In the FFXI universe, the orcs are beastmen who patrol various regions of the game, attacking adventurers at will - their reasoning for this? The very sword that Trion wields, one with enough power to separate a peninsula from the mainland and driving the inhabitants of a former powerful city underground. Rojgnoj tells all of this to us in broken English (or Japanese or French, depending on where you're playing from) and tells us this was the cause for the orcs waging war against the Kingdom of San d'Oria 20 years ago. It caused him and his people pain, and they simply wanted to destroy it. He dies shortly afterward.
 * Red Dead Redemption: "When I'm gone, they'll just find another monster."
 * Amber and Crystal Bailey from Dead Rising 2. You only have to kill one of them to win the Boss Battle, because when you do, the other will curse Chuck for taking away her "other half", and then commit Seppuku.
 * Cliff Hudson from the first Dead Rising is also an example. A Vietnam war veteran who is experiencing war flashbacks due to the death of his granddaughter at the hands of zombies, and has become psychopathic as a result. When in his death throes, he snaps out of his madness, resulting in an extremely sad death scene. He is one of the few Psychopaths that most players regret killing.
 * The two major antagonists of Golden Sun: The Lost Age, Karst and Agatio, die of hypothermia in Mars Lighthouse after being turned into dragons and forced to fight the heroes until they're too exhausted and injured to warm themselves or escape. Agatio, The Generic Guy to the end, pretty much just tells the heroes to continue their mission and fire the Lighthouse for them. Karst, on the other hand, received just enough Character Development to shed sympathy on her Roaring Rampage of Revenge, so when she begs Felix to comfort her, it's both surprisingly Moe for her and a flat-out Tear Jerker for us. Needless to say, a lot of fans rescue her in Fan Fiction.
 * In Devil May Cry, after you defeat the recurring Worthy Opponent Nelo Angelo, it's revealed that he was really Dante's twin brother Vergil. Vergil also qualifies for this in the third game, when he chooses to stay in the demon world after losing to Dante.
 * In the Dynasty Warriors series, Cao Cao was always portrayed as somewhat villainous and cruel. However, in the seventh game, it showed that beneath the coldness, he does care about the people who serve him, and he does wish for the chaos to end. Right before his death, he pleads for Xiahou Yuan and Dian Wei (both of whom died serving their lord) for their forgiveness.
 * The Nazis at the end of The Saboteur. As you approach their hideout in the Eiffel tower, you first assume that one of them has accidently fallen—you hear him scream and see him splat in front of you. Then, several of his comrades follow suit. The lobby is filled with dead, dying, or sobbing Nazis, one of whom drags himself towards you on his belly, choking out that, "He-he's killing everyone!" One of the soldiers plays a slow and mournful version of the game's theme, 'Feeling good', on the piano. To get to the elevator, you pass by a cluster of Nazis who hanged themselves, and at least two are play a tearful game of Russian Roulette with their pistols. Approach them, and Sean will murmur, "Keep at it mate--you'll get it right soon enough." Brrrr....
 * Ogura in the true ending of Densetsu No Starfy 3. The music doesn't help, either.
 * Many players get this feeling after killing Garl Vinland and Maiden Astraea in Demon's Souls.
 * Gogandantess from Onimusha 2: Samurai's Destiny. Despite his arrogance and the fact that he's, well, a demon, he is also one of the few Genma with a sense of honour and chivalry, and Jubei develops a respect for him, culminating in him actually rushing to Gogandantess' side to be with him in his dying moments, during which they both express their respect for each other. The music during the scene doesn't help, either.
 * In The Legend of Spyro: Dawn Of The Dragon, it's revealed that the Apes were given a Fate Worse Than Death by Malefor so terrible, it's rather hard not to feel some sympathy for them. They were turned into living skeletons, forever cursed to remain in the shadows and feed off the energy of others, unable to ever be full. Even Spyro and Cynder are visibly horrified by this.
 * Thorne in Tron 2.0. Yes, he was greedy and made an exceedingly stupid mistake (that laser caused his wife to die, and his best friend to vanish - Alan Bradley is not kidding about the safety protocols!). But his PDA testifies to a lonely, frustrated life (the contact list comprises work contacts, his mother, and a shrink), and he dies horribly (literally being eaten alive by The Corruption).
 * The Carpenter in Alice: Madness Returns, all of his actions involving sinking ships and building an underwater town were to protect his part of Wonderland from the Infernal Train. Said train smashes its way through the Carpenter's theatre, and he moves himself into its path so it doesn't hit Alice.
 * Surprisingly, vicious and psychotic villain Revas in The Chronicles of Riddick: Assault on Dark Athena manages this as she is suspended over an elevator shaft, just moments before her death:

"Batman: Do you know something funny? Even after everything you've done... "I still would have saved you.' Joker: (By now coughing uncontrollably) Heh... that's actually rather funny..."
 * At the end of Batman: Arkham City, he's been around two games while kicking dogs and generally doing his best to piss you off. However, the death scene of The Joker is surprisingly sad, even when you know he had it coming.


 * Portal 2 has GLaDOS and, arguably, Wheatley. Neither of them die, but during the core transfer, GLaDOS screams in pain and it's terrifying. Wheatley shoots right into antagonist territory, destroying her power. And then you transfer them again, and throw him into space, and he gets an absolutely heartbreaking apology monologue. It makes you wonder who to feel sorry for at that point.
 * The Great Wolf Sif in Dark Souls. He can't really even be called a villain—Sif is just having a knee-jerk reaction to someone trespassing near his friend's grave. Near the end of the battle, Sif even starts limping in pain as he valiantly struggles to protect Artorias' grave from an Undead monster (i.e. you). Sadly there's no way to spare him since you need Artorias' ring to proceed with your quest, and the only way to get the ring is by killing Sif.
 * Shinji Matou in Fate Extra. A Jerkass and a Smug Snake who is constantly treating everybody as if they were below him. But once he loses, he immediately starts lashing at his Servant for being weak and you for beating him; all while whining he does not want to die. Then, we get his last words:.
 * Dragon Age II has two major examples: . Both started out as reasonable people who were corrupted by a combination of   and both have tearjerking death scenes:
 * Duvall, the main villain in Haze, is an extremely arrogant and over-confident jerk for the entirety of the game. When's he fatally wounded in the final duel, however, it's hard not to feel sorry for him when he's sobbing, and then begs you not to tell his mom what he's done (slicing off fingers, killing people, etc.).

Web Comics
"Demon-roach: So what? Who cares? MitD: Exactly. That's why I'm sad."
 * Miko's death in The Order of the Stick. It's still debated on the forums whether or not she deserved it.
 * In strip 830, it's really hard not to pity Tsukiko—an unrepentant Card-Carrying Villain who sold out her own city to Xykon—when Redcloak usurps control over her wights, who she'd treated like her own children, to prove that undead are little more then automatons for necromancers of any stripe. And then he has them drain her to death. And then eat her. She was a sick, twisted, self-confessed necrophiliac who was obsessed with Xykon because every living person she ever met in her entire life treated her like crap. What puts her solidly in Alas Poor Villain territory is that she really and truly loved him, and only died because she discovered concrete proof that Redcloak is manipulating Xykon, and that the MacGuffin they're after won't get Xykon the power he wants. The point really gets hammered home when the only person to mourn is the Monster in the Darkness, who points out that in the end, Tsukiko just wanted to be loved.


 * Whenever Oasis dies in Sluggy Freelance, it's treated with sadness, even when she's been in full-on Ax Crazy, Stalker with a Crush mode, since we know she's only like that because Dr. Steve Brainwashed her. However, as Oasis becomes more heroic and we learn she'll always come back from being killed, this has faded.
 * The entire cast of The Last Days of Foxhound. Except Mantis and Ocelot.
 * Violent Glaswegian Dougie in What the Fu suffers a breakdown from the revelation that he's not actually Scottish. Zac almost feels sorry for him, except he's "still a murderous psychotic bastard".
 * Homestuck:
 * Vriska Serket, who had spent the entirety of Act 5 Act 2 getting closer to John and finally admitting that she wanted to try living a normal life. She was killed by Terezi in order to prevent her from fighting Jack, which in an alternate timeline got everybody except Vriska and Aradia killed. Her final message? Telling John that if and when they finally do meet, she'd like to go on a date.
 * Courtyard Droll, Jack's clueless underling who pretty much fails at being evil, which gets his superiors pretty annoyed with him. When he finally manages to follow one of Jack's orders to the letter (Jack had ordered him to kill Jade, something Jack himself couldn't do due to his Undying Loyalty from Bec's prototyping), Jack snaps and kills him.
 * In Our Little Adventure, in universe, the body gets dump with the epigraph: You poor, stupid kid.

Web Original

 * Happens quite often in Survival of the Fittest:
 * Bobby Jacks' death, committed after realising the path he took. Read it here.
 * Laeil Burbank goes out with a fairly tragic death, accented by how violently and sadistically she received her fatal injury and how she was almost saved. Found here.
 * Clio Gabriella gets a fairly touching send-off, dying in her boyfriend's arms while she begs for him to save her after being shot. Again, readable here.
 * In the tradition of its source material, Stray does this for one of its villains - the Tyke Bomb Patriot agent Esau.
 * Mega 64 Version 3 ends with the legitimately tragic death of Dr. Poque, who started the series as the main antagonist.
 * In the Global Guardians PBEM Universe, the villain Hardcase was generally thought of as a brutish, selfish thug who liked to beat up women for fun, drank too much, and was generally a sleaze. And on September 11, 2001, he gave his life by using his superhuman strength to save people from the collapsing North Tower of the World Trade Center. The heroes not only campaigned to get him a posthumous presidential pardon, they sprang for a funeral the likes of which are normally reserved for deceased presidents and popes.

Western Animation
"Cheetor: He wasn't just one of us... He was the best of us."
 * In Beast Machines, Rhinox, a former ally, has become Tankor, a powerful enemy. After Tankor's death, the heroes hold a memorial for their fallen friend.

"Batman (Terry): Freeze, you have to get out of here! The whole place is coming down! Freeze: Believe me... you're the only one who cares."
 * It's debatable whether Starscream in Transformers Armada even counted as a villain anymore by the time he had his Redemption Equals Death moment, but Megatron definitely counted.
 * Ditto for Scorponok in Transformers Energon.
 * Also, Demolishor, although he got better.
 * In nearly every Mr. Freeze appearance in the DC Animated Universe (except the one where he finally gets a happy ending and the one from The New Batman Adventures), he is defeated in a notably tragic and even Tear Jerky way, culminating in this final exchange in his last appearance (both in Real Life and in the Universe timeline), where he allows himself to be caught in a collapsing building.

"Grundy: Do you think... Grundy's soul is waiting for him? Hawkgirl (A confirmed atheist): Grundy, I don't belie- (stops herself) Yes. It's waiting for you. Grundy: Then Grundy... gets his reward."
 * Don't forget Solomon Grundy, who, in a single episode (or rather two connected ones), goes from regular villain to sympathetic villain, who dies in his quest to attain his lost soul. For good measure, he's brought back again in a later episode, this time truly souless, and has to be put down Old Yeller style.

"Demona: The access code is... 'alone'."
 * This happens a lot in the DCAU.
 * While Cobra Commander was always an ineffectual coward in G.I. Joe, one can't help but feel for him in The Movie where he is lying on the ground, in agonizing pain, having been exposed to virulent spores that are mutating him into a snake, and slowly losing his mind.
 * Though she doesn't actually die there, Demona's defeat at the end of "City of Stone" certainly counts, as a broken Demona, for a brief moment, realizes and regrets the evil she's done over her thousand-year life, and then gives the heroes the password they need to shut down her scheme. It doesn't hold, but for a moment, you stop hating her and just feel sorry for her.

"Leonardo: You heard the man. Let's go stop the Shredder."
 * Especially since, when you stop to consider who is actually responsible for what, Demona is actually only the 4th most responsible individual for the original slaughter of the clan, preceded by Hakon (the guy who actually did the smashing), Princess Katherine (the racist brat whose contempt for the beings safeguarding her and her people went beyond Broken Aesop), and the Captain (who combined her betrayal with passing up the opportunity to risk himself to stop Hakon from smashing the sleeping gargoyles), and she's just ahead of...Goliath himself, whose ready acceptance of Katherine's abuse resulted in the injustice shown to his own clan's children. The only people living who really had a reason to hate her at that point were the surviving kin of the few people she killed during "City of Stone".
 * Speaking of the Captain, he was so wracked with guilt that he spent the next thousand years haunting the castle's remains after his death. Hakon was also haunting the site, but out of continued hate for Goliath (who killed them both Disney style, although he wanted a far more gruesome kill). When Goliath shows up at the castle again, they harass him, make him hallucinate and attack his own friends, and, finally, drive him to an ancient ritual site where they can exchange his life for theirs. The Captain realizes what evil he is about to commit, repents, and uses his brief physical form to destroy the site. With his last moments, he thanks Goliath for forcing him to acknowledge his sins and begs for forgiveness as he travels to the afterlife. This is such a Crowning Moment of Awesome that Goliath happily mourns him as a friend who is finally at peace. Hakon is still stuck, trapped within the ruined site, alone to wallow in his hate.
 * Hard not to feel a little bad for Azula by the end of the finale of Avatar: The Last Airbender. You may remember her from works such as that time she fried Aang, that time she inexplicably gave Zuko credit for it, or that time she ruined an invasion -- without firebending—using only her natural skills in acrobatics, taunting, and sarcasm. The past few weeks haven't been so good; she lost all her friends, she got rejected by dad, she banished all her servants, she chopped off a bunch of her hair, she hallucinated her mother simultaneously shattering her worldview and saying she loves her, and she lost to her loser brother and a peasant. Once an irresistably sinister and brilliant prodigy, she is left chained to the ground, madly wailing, sobbing, and breathing fire at the sky. Well, at least she can still firebend.
 * General Shiva in Exo Squad; imprisoned for not slaughtering the Australian Resistance to the last man, he is given a chance to "redeem himself" by retaking Venus, which he knows to be a suicide mission. But, being a good soldier, he gives it a go anyways. When he gets shot down, even the Exoscouts who find him see it as a tragedy.
 * While he has a number of fans who sympathize with him, Vlad Masters in Danny Phantom remains the overall Big Bad and performs his share of Moral Event Horizon acts. Still, his final moments gave him a big woobie moment when he not only had to deal with the fact that everyone he wanted would not give him their love, but his most hated "friend" of all people rejected him when he refused to change his evil ways. Now, Vlad doesn't have anyone and is stuck in an area where he has to confront his greatest fear: loneliness.
 * Hun in Turtles Forever, after the Turtles finally convince him that The Shredder is going to destroy The Multiverse. Hun is erased from reality right afterwards. Of course, the same thing happened to Casey and April, and we see them both get better once reality is restored, so we can assume Hun was brought back too.

"I PROMISE I'LL PAY Y'ALL BACK!!!! I JUST NEED A LITTLE MORE TIME!''"
 * The Princess and the Frog: He spent nearly the entire movie trying to kill Big Daddy and enslave the souls of the entire city of New Orleans as a goodwill payment to his ''friends", and mode-locked Naveen into a frog, but if you don't feel even the least bit of pity for Doctor Facillier at the end of the movie, I worry you may not have a soul. He is, literally and rather graphically, dragged into Hell by his shadow, screaming and begging the entire time. It's so bad that Tiana, whom he just put in a Lotus Eater Machine and is the indirect CAUSE of his death, can only watch in abject horror.

"Nox: Twenty minutes? All that wakfu spent for a jump of twenty minutes in time? Two hundred years of researching and collecting wakfu for twenty mere minutes? NOOOOOO!"
 * About the only way you won't feel pity is if you're too busy being scared out of your mind by the puppets and Tiki/Voodoo masks chanting, flailing away on drums, and screaming/singing "ARE YOU REEAAADY!?" Being Disney, it very easily could have fallen into Narm territory... It didn't, because his soul is being collected by his own Villain Song!
 * Wakfu, at the end of the series. Poor Nox.


 * Actually, he doesn't die then. Instead, he goes to the grave of the family he loved so much and quietly kills himself. Which is even more depressing.
 * In the Fantastic Mr. Fox, all the animals are saddened by the death of Rat, even Fox himself (who dealt the killing blow), despite his being the traitorous head of security for farmer Bean. In fairness, Rat did manage to come to his senses in his few final moments when he revealed that he had turned traitor because he had become too addicted to the apple cider of Bean.
 * The death of Spider-Carnage in Spider-Man: The Animated Series. He was a demented, Axe Crazy loon who was trying to set of a Class Z apocalypse, but when he has a Heel Realisation and kills himself it's all but impossible not to feel bad. There's just something about seeing someone with the face of the show's hero brought so low that not only does suicide seem like a good idea, it's the best option that there is.

Real Life

 * During the American Revolution, the death of John Andre, who was executed as a British spy, was mourned by British and Americans alike.
 * Likewise, Manfred von Richthofen, the Red Baron, inspired such respect in his enemies that when he finally did fall in battle, they showed him the utmost respect and buried him with full military honours, with enemy airmen serving as his pallbearers.
 * Some English citizens were reputed to feel this way towards Joan of Arc when she was burned at the stake, according to The Other Wiki. Her executioner, Geoffroy Therage, later stated that he feared he'd damned himself. Of course, Joan of Arc wasn't a villain, just an enemy of the English. Nowadays, most consider her execution wrong, and thus the feelings of sadness are justified.
 * Juan Camilo Mourino, a Mexican politician of Spanish ancestry holding the position equivalent of vice president. Frequent target of left-wing political cartoonists and activists who accused him of being a foreigner and wanting to privatize the Mexican oil industry. Then, on November 2008 he died on a plane crash, making his former critics to mourn him. In fact, one of his most rabid cartoonist critics made an eulogy in his blog titled "When Death doesn't laugh".
 * Muammar Gaddafi. As horrible as he was, his death was just so brutal that a lot of people couldn't help but feel sorry for him.