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* ''[[Naruto (Manga)|Naruto]]'': many, if not ''most'', of Naruto's opponents over the course of the series, notably:
** Gaara of the Sand before {{spoiler|Naruto beat the crap out of him.}}
** Sasuke's status is [[Base Breaker|debatable]], but he essentially [["Well Done, Son" Guy|struggled for his father's approval]], only to lose his entire family in the Uchiha clan massacre.
** Neji is introduced looking down on his teammate, Lee, and hating Hinata enough to [[Hannibal Lecture]] her about her inferiority and trying to kill her. It is later revealed that he believes that his father was killed for the main branch when he was young, and he can be punished at any time, potentially fatally, if the Main Branch members activate the Cursed Seal on his head. Once he learns the truth, he overcomes his previous belief that [[You Can't Fight Fate]], which results in him working to improve his relations with the main family and getting along with Lee when he isn't acting too eccentrically.
** Pain is responsible for many deaths, {{spoiler|razed the Leaf Village and almost killed Hinata}} to teach Tsunade and Naruto lessons about pain, and is incredibly ruthless toward his goal of enforcing peace with tailed beast-based jutsu weapons, but his childhood was a long process of losing everyone he cared about and trying and failing to bring about peace.
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* Bonten from ''[[Amatsuki (Anime)|Amatsuki]]''.
* A large portion of the cast of ''[[Code Geass (Anime)|Code Geass]]'' not only do nominally immoral things for their cause, but also find themselves treating others poorly when it's obvious that either that's not what they really ''want'' to do, or they're too far gone to really do anything: Lelouch, Suzaku, Kallen, C.C., {{spoiler|Rolo, [[The Emperor]], Marianne, Guilford...}}
** There's also Mao, who takes this trope in a different direction. His personality is [[Jerkass|abrasive]] and many of his actions are [[Moral Event Horizon|utterly cruel]] but he [[One -Scene Wonder|still]] inspires sympathy from some measure of the viewers once they learn that he's essentially [[Adult Child|a child in the body of a seventeen-year-old]] who has [[Moral Myopia|no sense of perspective whatsoever]], [[Unhappy Medium|in constant pain]] [[Blessed With Suck|from his mind-reading Geass]], and abandoned by [[Single Target Sexuality|the one person]] who could interact with him at all normally (who is also [[Love Martyr|the only person he loves!]]) because he couldn't bring himself to {{spoiler|killing her and taking her immortality, and because she [[What an Idiot!|actually thought that it was a good idea]] to leave him to live totally alone for the rest of his life.}} And all because he became an [[Unhappy Medium]] at the age of ''six!''
* Misa Amane from ''[[Death Note (Manga)|Death Note]]''. If she weren't so damn amoral, she'd be a very sympathetic character - what with her [[Parental Abandonment]] issues and her devotion to Light, which is both ''very'' crazy (seeing as how he doesn't really care about her at all and is merely using her as a pawn and eventually wants to kill her when she outlives her usefulness) and ''very'' genuine. She, ultimately, is an aversion (at least to [[Americans Hate Tingle|American audiences]]), due to the fact that her abandonment issues are rarely focused on--rather, her bubbliness and cluelessness are.
** She turns even more woobie-ish when {{spoiler|you learn she kills herself eventually.}}
** Her live-action movie incarnation is even more of an example of this trope, as the death of her family is more focused upon (she mentions that she's fine with dying because "she should have died along with her family" when they were murdered, and she even keeps a picture of them in her room next to one of Light). The movie also shows that, if not for her insane fixation with Light, she could be a good person (she ends a killing spree out of hesitation when called a murderer, and later cries when she realizes that Light {{spoiler|is willing to kill his own father.}})
*** Misa in custody. Imagine the mental state of the poor girl. {{spoiler|She's taken off the street, continuously blindfolded and restrained for two ''months'', under constant surveillance, and ''she has no idea why she is there or if she will ever be untied.''}} If she wasn't crazy before, she has every excuse to be afterward.
** To a smaller degree, Kiyomi Takada. Specially because of {{spoiler|[[Alas, Poor Villain|her VERY ugly death]], [[You Have Outlived Your Usefulness|orchestrated by none other than]] [[Villain Protagonist|her beloved Light]].}}
** Light Yagami himself qualifies. He [[Used to Be A Sweet Kid]], he was a [[Nice Guy]] with a bright future ahead of him before becoming a [[Serial Killer]] with a [[A God Am I|God Complex.]] [[Word of God|Even the author]] says his life was ruined the moment he picked up the Death Note [[Break the Haughty|and over the course of the series he gets put through hell]] and {{spoiler|fails and dies horribly in the end}} ''but'' he has no one to blame but himself.
** Mello, a mob boss that kidnaps innocent (and not-so-innocent) girls and [[Arson, Murder, and Jaywalking|a overbearing jerk that shouts at people]] but he acts that way out of a severe inferiority complex. He {{spoiler|blows up his base, blows up his face, gets his best friend killed, and dies horribly at the hands of Takada.}}
** Beyond Birthday from ''[[Death Note (Manga)|Death Note]]:'' ''[[Another Note (Light Novel)|Another Note]]''. L's neglected [[Beta Test Baddie|Backup]] turned [[Serial Killer]]. As much of a [[Complete Monster]] he was, {{spoiler|he was born with the ability to see when everyone is going to die, he was raised at an orphanage, neglected by his role model, and saw his classmate commit suicide (and of course knew it would happen). He's batshit crazy and totally psychotic but ouch, he attempted to burn himself alive!}}
* Lucia from ''[[Rave Master (Anime)|Rave Master]]''. The one that had to watch his mother die and got locked up for ten years for no reason when he was 6, and proceeded to commit mass murder immediately after escaping.
* ''[[One Piece (Manga)|One Piece]]'' has Nami, the self-centered, [[Tsundere|mood swinging]], thieving [[Insufferable Genius]] of the Straw Hat Pirates. However, her personality, in particular, her obsession with money, [[Freudian Excuse|is explained as a result of being an orphan raised]] by the Marine officer Bellemere, along with Nojiko. The family was too poor to afford the things Nami wanted, and when [[Complete Monster]] [[EverythingsEverything's Even Worse With Sharks|Arlong]] came along and imposed a tax on the people in her village, with the penalty for not paying as death, Bellemere only had enough money to pay for two. She chose to save her children rather than herself, and was shot in front of her children's eyes. Arlong then forced Nami to be a part of his crew, even going so far as to [[Tattooed Crook|forcibly tattoo her]], and said that if she manages to get 100 million belli, her village will be freed as well as herself. Even worse is that [[I Lied|Arlong had no intention of keeping his end of the bargain]], and wanted to enslave her for the rest of her life. Good thing she met Luffy and the other [[Ragtag Bunch of Misfits]] who dealt with Arlong personally.
** Similarly, Boa Hancock was introduced as a literally [[Kick the Dog|puppy-kicking]] [[Vain Sorceress]]. She showed herself to be an aloof, arrogant, complete [[Jerkass]] who wasn't above defenestrating her grandmother for giving the sincerest of warnings and [[Taken for Granite|petrifying]] her subjects for allowing a man (Monkey D. Luffy) [[Lady Land|onto their island]]. She was even complacent with her two younger sisters, Marigold and Sandersonia, ''breaking them in their petrified state'' just to mess with Luffy - just a hair's breath of crossing the [[Moral Event Horizon]]. However, when Luffy defeated the sisters and spared their pride by hiding their tattoos, this brought to light another side of Hancock unseen before: as she explained to Luffy, the tattoo was forced upon Hancock and her sisters (sensing a pattern here...), and is an eternal source of shame from slavery under the [[Aristocrats Are Evil|World Nobles]], descendants of the founders of the World Government and, as shown in the previous arc, a whole 'nother ball of the MEH wax, known for kicking, shooting, and ''blowing up'' their slaves if they get frustrated or bored with them. The three sisters, who were just pre-teenage girls back then, spent four whole years enslaved to those [[Complete Monster|Complete Monsters]] and were force-fed a Devil Fruit [[For the Evulz|strictly for their entertainment]]. Hancock's own experience was such that she couldn't even talk about it without being reduced to tears. The very fact that she kept the law of her island to the letter could be explained due to her personal experience with one particular World Noble who was in her words "the very object of terror itself", [[Does Not Like Men|which jaded her view on the opposite gender]]. It's only that Luffy didn't care that she and the other two were slaves, and hates the World Nobles anyway (for shooting a friend of his, who ''wasn't even one of their slaves'') that caused [[Defrosting Ice Queen|her icy persona to warm up a bit]], and even fall in love with the guy.
* Shinn Asuka from ''[[Gundam Seed Destiny]]''. Yes, he may be an abrasive jerk who needs to wake up and stop seeing the world in black and white, but during the story, he goes through such hell that you can't help but feel sorry for him. Especially considering how badly Sunrise and [[Fan Dumb]] abused him, coincidentally contributing to his total breakdown.
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** Once you get glimpses of their backstories as {{spoiler|[[Artificial Human|Artificial Humans]] who were bred ''only'' to pilot Gundams}}, the Trinity siblings from [[Gundam 00]] come off a pretty damn pitiful. Of course that does '''not''' excuse the heaps of shit they pull on everyone [[Even Evil Has Loved Ones|except for each other]].
*** [[The Smart Guy|Tieria Erde]]. At first, he's cold, stern and the most dedicated to Celestial Being's mission. However, after (thefirst) Lockon's death in season 1 and the separation from VEDA, we see that Tieria is a very insecure man.
* Any teen character in ''[[Ranma One Half½ (Manga)|Ranma One Half]]'' you might be inclined to feel sympathy for is a [[Jerkass Woobie]].
** Ranma Saotome has had a ''horrible'' childhood that, among other things, means that he has been inflicted with a [[Gender Bender]] curse that not only embarrasses him and frequently gets him into strife, but puts him at the risk of having to commit [[Seppuku]] at the hands of his [[Yamato Nadeshiko|good-hearted]] but [[Cloudcuckoolander]] [[Hot Mom]] -- which means that he will not only die painfully, but die knowing that he disappointed his beloved mother so badly that she thought it would be best to die. He also routinely harasses his (admittedly, no saint herself) fiancée by hitting her where it hurts her the most (her ''relatively'' small chest [in comparison to his [[Gender Bender]] form and the rest of his fiancees]] and her inability to be properly feminine no matter how hard she tries), sometimes actively encourages his fiancées, and loves to harass and torment his rivals, despite ''knowing'' that they'll come after him with the aim of brutally thrashing him.
** Ryôga Hibiki has terrible luck, is cursed to assume the form of a [[Baleful Polymorph|small, defenseless pig]] when he gets wet, has one of the worst ever seen cases of [[No Sense of Direction]], the direction issues are inherited from both his parents and so he almost never sees his family, is a [[Courtly Love|dedicated romantic]], is too shy to even talk to other girls (despite the fact most would probably find him [[Mr. Fanservice|highly attractive]]), and the one girl he's in love with is engaged to someone else. He's also bad tempered and masquerade as her pet to get affection from her, even if it's only as her pet.
** Mousse spins a heartbreaking tale of devotion and unrequited love that spans the better part of a decade, refusing to give up on his attempts to woo his childhood acquaintance no matter what blows life deals, to the point that an audience in-series cries after hearing it. However, the object of his affections makes it clear that he's more a [[Stalker With a Crush]] who happens to have been a childhood friend than the [[Unlucky Childhood Friend]] he sees himself as. There's also the fact that his response to the [[Love Triangle]] he's personally caught in as part of the [[Love Dodecahedron]] is to literally [[Murder the Hypotenuse]], and as he [[Blind Without 'Em|has very poor vision]], even ''with'' his glasses, and literally doesn't care who gets in the way...
** Akane Tendô is [[Naive Everygirl|a generally nice, placid]] [[Girl Next Door]] who has [[Overshadowed By Awesome|lost her position as]] [[Action Girl|the best martial artist around]], [[Can't Catch Up|seemingly irreversibly]], and been saddled [[Arranged Marriage|against her will]] with a fiancé who seems to enjoy hitting her most sensitive spots, like her "modest" figure (in comparison to [[Gender Bender|his]] own and those of her rivals) and her failure to become a [[Yamato Nadeshiko]] which is one of her greatest wishes. On the other hand, she's prone to [[Tsundere|tremendous mood swings]], jabbing him where it hurts as well, manipulating him for her own purposes, and lashing out [[Armor -Piercing Slap|violently]] when he does something that she suspects is perverted...and she has very little trust for him ''not'' to do something perverted.
** Shampoo, particularly in the anime, genuinely loves and cares for Ranma, but gets little affection from him. Due to his [[Harmful to Minors]] training and a [[Baleful Polymorph]] curse inflicted on her as punishment early in the series, he actually runs away from her quite frequently. She's also a stranger in a strange land and has no friends at all outside of Ranma and Mousse (Akane might have counted as well if she and Shampoo had not been rivals in love). However, she's also coldly efficient to the point of being frighteningly amoral, perfectly willing to kill off someone she considers an enemy, and her preferred victims are the aforementioned Mousse and Akane, treating the first with incredible cruelty and being determined to get rid of the latter.
** Ukyô Kuonji is Ranma Saotome's [[Unlucky Childhood Friend]], who felt so ashamed after Ranma apparently broke their [[Childhood Marriage Promise]] and stole her father's cart that she devoted her life to seeking revenge and even became a [[Wholesome Crossdresser]] because she felt that she was unworthy of being a woman. Even when she gives this up and tries to resume her courtship of Ranma, he not only does his best to avoid giving her any romantic favors at all, but he ruthlessly exploits her feelings. However, she is also quite willing to beat the hell out of any perceived rivals for his hand, slap Ranma around if he gets her flustered and upset, and team up with others (like Ryoga and Shampoo) to try to get the upper hand.
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* ''[[Axis Powers Hetalia (Manga)|Axis Powers Hetalia]]'':
** Ivan/Russia. A creepy, mentally unstable [[Stepford Smiler]] who [[Psychopathic Manchild|has fun]] terrifying and abusing his subordinates, especially [[The Woobie]], Lithuania...but his [[Despair Event Horizon]]/[[Start of Darkness]] is nothing short of heartbreaking, and he truly loves his [[Fragile Flower]] older sister, Ukraine, as much as his insanity lets him. You also can't help but feel sorry for him as he's constantly being pursued by his even crazier sister, Belarus, who wants to marry him. Also, Himaruya's new profile on him points out that he truly wants to have new friends. However, if that is true, it won't happen, because he's so scary that he ends up driving away potential friends.
** Gilbert/Prussia can also qualify. He's an unrepentant, egotistical [[Memetic Badass]] who delights in causing trouble for others and seems to only think about himself...but at the same time, he's also something of a [[Butt Monkey]] who [[Small Name, Big Ego|isn't as awesome as he likes to think he is]], and is shown to be secretly lonely and trying to pretend that he doesn't care about not being a nation anymore or not having any friends at all. And if you see him with [[Shipping Goggles]] on, there's the added "pain" of being the [[Unlucky Childhood Friend]] to a [[Ninja Maid]], who's head over heels in love with the local [[White Prince]].
** [[Fanon]] sometimes interprets England as this, with him being quite ruthless and manipulative in his acquisition of his empire and family members and them eventually leaving him alone and lonely. Whether or not he actually ''is'' one in canon depends HIGHLY on [[Alternative Character Interpretation|your personal interpretation of his character]], considering that the one who broke his heart the most was one he was shown to care very deeply for and take good care of in canon, which would probably make him a straight-up [[The Woobie|Woobie]] instead.
** Japan sometimes gets this kind of interpretation too, from fans who believe that as ruthless and double-crossing as he may have been toward his siblings during his [[Imperial Japan|imperial period]], he probably still did not deserve to have two atomic bombs dropped on him and may very well have become as [[Break the Cutie|emotionally]] [[Broken Ace|broken]] as his siblings in his [[Well -Intentioned Extremist|misguided]] [[Lonely At the Top|pursuit of empire status]].
** Romano, the elder of the Italy brothers and a notorious [[Tsundere]], has shades of this: harboring a [[Hair -Trigger Temper]] and generally negative demeanor, yet also having an inferiority complex and abandonment issues stemming from [[Parental Favoritism|his grandfather ignoring him in favor of his more talented younger brother]] and feeling like others only wanted to use him for said grandfather's inheritance. An early profile even stated that being pushed around by [[The Mafia]] made his viewpoint of the world more slanted and negative. Of course, [[The Woobie|the more sympathetic traits]] run the risk of being blown out of proportion by Fanon, where [[Fan Dumb|some fans]] opt to [[Ron the Death Eater|lay all the blame instead on the younger brother, Veneziano]], who ''does'' care for his "fratello" and tries to help him with mixed degrees of success.
** Belarus, a terrifying [[Ax Crazy]] [[Yandere]] became this when Russia threatened to send her to Siberia because Lithuania expressed reservations about accompanying him to a meeting. Can you imagine your own brother caring so little about you that he uses sending you to the horror that was the gulags as an incentive to make someone else do what he wants? If this happens on a regular basis, her bitterness comes as no surprise. Even if it's Belarus, that's just not right. There's also the fact that the poor girl is hopelessly and creepily but also very genuinely in love with Russia, her brother, who will never, ever return her feelings. Of course, let's not forget the [[Jerkass]] part, specifically how she scares off anyone who is around her brother because she's jealous of them and how she once broke Lithuania's fingers on a date with him (the poor guy is such a sweet [[Nice Guy]]... but he refuses to see that Belarus not only is flawed, but that [[Dogged Nice Guy|she does NOT owe him pussy just because he likes her]].)
** Even though France is a [[Anything That Moves|lech]], a liar and an all around [[Manipulative Bastard|bastard]] at times, he has his moment to be pitied. At the end of the first volume, there is a sketch of a much younger France with a girl with short hair and wearing armor. And she tells him, "I'm fighting for you, you know!" Yeah, she's Joan of Arc. We know how that ended. To think of France, hedonistic and arrogant, startled and then drawn to this one girl, only to lose her- it makes you feel for him at least a little, right? That's not counting the French Revolution, the Terror...on second thought, those pretty much explain (along with Jeanne's death) why France became the way he is.
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** Also Aki of ''[[Yu-Gi-Oh 5 Ds (Anime)|5Ds]]''. Yes, she was ostracised as a child by her parents for having magic powers, and subsequently found by a lunatic who wants to rule the world for no adequately explained reason other than "I'm different and therefore I should be on top of the world". But that smile she wore when using her magic powers when dueling, especially against Yusei, was damn creepy.
* ''[[Black Lagoon (Anime)|Black Lagoon]]'':
** Hansel and Gretel. It gets easy to see why they were so fucked up and 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]] moment when Rock offers her kindness and even sheds tears for her. When they finally reach a seaport and her wish is granted, she has her brains blown out by an assassin hired by Hotel Moscow.
** Also, Balalaika. Thanks to the Afghan War, the cute teenager who wanted to become an olympic sniper ended up as a cynical, stylishly brutal Mafia queen and cold-hearted [[Magnificent Bitch]]. She's also quite the [[Mama Bear]] who shows no mercy to anyone who harms her subordinates, which proves that she's still human: those men are all she has anymore, so she protects them fiercely.
* ''[[D Gray Man (Manga)|D Gray Man]]'':
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* Akira Inugami from ''[[Wolf Guy Wolfen Crest (Manga)|Wolf Guy Wolfen Crest]]''. He rescues his [[Morality Pet]] teacher from baddies regularly, gives hope to his oppressed fellow classmates, and stops an [[Ax Crazy]] psycho from gunning down the student body vice president at point-blank range, but he can be a cold-hearted snarky jerk to everyone. He also lost his parents at a very young age, has a habit of making enemies who want to violently beat him up and murder him, and is pursued and lusted after by ''two'' [[Ax Crazy]] psychos who are major threats to anyone he is close to or not. Basically, he's a nice guy [[Jerk With a Heart of Gold|underneath]] it all, but he spares NO ONE the [[Deadpan Snarker|snark]] and is literally the [[Doom Magnet|unluckiest bastard walking.]] Which backfires horribly when {{spoiler|his beloved teacher becomes his [[Morality Chain]] -- and one of the [[Ax Crazy]] psychos has her kidnapped and gangraped. Which causes Inugami a heartbreaking [[Heroic BSOD]].}}
* ''[[Berserk (Manga)|Berserk]]'':
** Although he claims to be a complete asshole, Guts is actually a [[Jerk With a Heart of Gold]] who simply acts aloof and unreasonable towards anyone he meets, including his [[True Companions]]. He does truly care for his companions, but since the Brand of Sacrifice he bears attracts monsters from hell, and his [[Hell Hound]] [[Super -Powered Evil Side]], the Beast, tends to make him [[Unstoppable Rage|go berserk and thus dangerous even to his companions]], he prefers [[Its Not You Its My Enemies|to keep them at a respectful distance]]. Also, he is ''very'' much a [[The Woobie|Woobie]]. Probably the biggest one in the entire cast, because the [[Crapsack World]] he lives in has had it in for him and those he loves ''since the moment he was born''.
** Griffith too. Until he crossed the [[Moral Event Horizon]] and became [[Complete Monster|utterly unsympathetic]].
** Rosine, the [[Big Bad]] of the Lost Children arc, qualifies because of the horrible home situation that drove her to become an Apostle, and her yearning for elves to be real. Though she and her "children" commit a number of acts that should make her cross the [[Moral Event Horizon]] into [[Complete Monster]] territory like many of ''[[Berserk]]'''s other villains, she comes across instead as a misguided, emotionally damaged little girl who just wanted a little happiness that she couldn't find at home.
* Souma and Sakurako from ''[[Sakura Gari (Manga)|Sakura Gari]]''. Initially, it seems as if [[ItsIt's All About Me]] with them, and they'll do whatever it takes to get what they want even if they hurt/kill others in the process. Also, every one of Souma's lovers are shown to have horrible endings. He even notices and mentions it himself. Of course, this doesn't stop him from continuing to take lovers. However, even with all their flaws, it doesn't make their [[Break the Cutie|backstories]] and [[Downer Ending|endings]] any less heartbreaking or messed up. And at the end, due to his actions, Souma ends up driving away Masataka, who he had genuinely fallen in love with, and, in the last panel, he is shown crying into one of Masataka's shirts. And as for Sakurako, {{spoiler|we find out that she's actually a ''boy'' named Youya, desperately lonely and unstable after [[Go Mad From the Revelation|his/her mind totally breaks when s/he was a child]], and s/he ends up commiting suicide when s/he thinks s/he's killed Souma.}}
* ''[[Pandora Hearts (Manga)|Pandora Hearts]]'': Oz and Vincent.
** And Break. Sure, he's not always nice, and it's not obvious that he's a [[Jerk With a Heart of Gold]], but he does have his moments. In the past, {{spoiler|it's revealed that he signed an illegal contract to try to change the fact that the family he was bound to protect was betrayed and massacred. Then, he was dragged into the Abyss and had his eye torn out, only to have the family die off anyway.}} Currently, {{spoiler|he's going blind in his remaining eye.}}
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** Hitagi Senjougahara. She acts cold and abusive towards others, especially towards her eventual boyfriend, Koyomi Araragi. She also pulls out a stapler and a box cutter, threatens Koyomi with them by shoving them in his face, and promises to disfigure him with them if he reveals her secret, then uses them anyway (stapling his face as a warning). All this within minutes of the start of the first episode. In episode two, Hitagi recounts how her mother joined a cult when Hitagi was sick, and that one night, her mother brought a higher up from the cult home. Hitagi injured him as he attempted to sexually assault her, while her mother watching without aiding her. As a result, her family was broken apart with Hitagi feeling that she's responsible. After that, she met a crab which took her feelings(weight) and memories of her mother. Hitagi begs the head crab to return to her the lost memories of her mother and her feelings(weight), but despite this, she has forever lost her mother.
** Mayoi Hachifuji. She knows that she is caught in or actually is a supernatural event and doesn't want anyone else to have to get involved. She's a 'snail,' otherwise known as a spirit that distracts people who are avoiding going somewhere and makes them follow her. She knows that she's dead and won't reach her destination, so she tells anyone who talks to her that she hates them so they'll leave her alone and not waste their time on her.
* ''[[Durarara (Literature)|Durarara]]'''s Shizuo Heiwajima. Underneath the [[Hair -Trigger Temper]] and violent, vending-machine-throwing rages is a guy with a severe impulse control disorder that knows fully well that his behavior and strength hurts other people, [[I Am a Monster|hates himself for it]], and [[I Just Want to Be Normal|wants nothing more than to be able to stop and control himself]], but has no idea how.
* ''[[Baccano (Light Novel)|Baccano]]'': hey, everyone, meet Czeslaw Meyer. A [[Really Seven Hundred Years Old]] [[Crazy Survivalist]] who uses [[Adorably Precocious Child|his appearance]] to manipulate people. Tried to get someone to kill dozens of people in the hope of finding one immortal. Is a [[Crazy Survivalist]] because {{spoiler|the guardian he'd trusted [[Fate Worse Than Death|spent 200 years torturing him]] in every way he could think of, supposedly to "test the limits" of their immortality. Czes only escaped by ''eating him'', absorbing all his memories of gleefully tormenting the poor kid [[For the Evulz]].}}
* Sae Kashiwagi of ''[[Peach Girl (Anime)|Peach Girl]]''.
* ''[[Samurai Champloo (Anime)|Samurai Champloo]]'':
** Mugen is a crazy, [[Badass]], insane [[Anti -Hero]] whose childhood makes anyone want to cry...
** Jerkass may be a strong word, but Fuu fits as well. She's often temperamental, unappreciative of her bodyguards (to be fair, they do abandon her a few times), and seems to recklessly search for someone with almost no leads. But like Mugen, she's also lonely and her search for the sunflower samurai turns out to be {{spoiler|because he abandoned her mother.}}
* ''[[Kaze to Ki no Uta (Manga)|Kaze to Ki no Uta]]'':
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** Muramasa. Sure, he personally instigated the [[Empathic Weapon|Zanpakuto]] Rebellion and {{spoiler|incinerated Katen Kyokotsu and Sogyo no Kotowari to death}}, but as Kouga descended deeper into madness, he quickly became a [[Smug Snake|self-centered, arrogant, abusive]] [[Jerkass]] that frequently treated Muramasa as a mere tool, instead of an actual person. However, since Muramasa was the one that led Kouga to his crazy, power-drunken self, one could say that he brought it on himself. This disharmony caused Muramasa to literally lose the ability to hear his master when needed...which led to Kouga [[Kick the Dog|stabbing]] Muramasa as soon as he was unsealed, completely uncaring about Muramasa's explanation.
** Also, Homura from the third movie. There's no denying that Homura was a stubborn, jealous, possessive, and irrational teenage girl, who had the potential to be as unstable as Loly can get at times, with an almost-unhealthy obsession towards Rukia to top it all off; but for all her faults, she was a sincerely sweet and cheerful girl, whose only wish was to reunite with the only other friend and loved one she had. In fact, she wasn't even evil to begin with, just selfish, naive, and misguided, with a justifiable excuse for her implied hatred (and fear) of the Shinigami. Considering her past, her interactions with Rukia are all the more heartwarming; as an orphan, she was forced to survive on her own in a lawless slum district, ended up getting murdered by an (albeit mind-controlled) Shinigami, absorbed said mind-controlling hollow into herself as a fail-safe to keep it from killing Rukia (thereby making it into the subconscious source of her power), and unintentionally causing the now-innate hollow spirit energy to revive and transport them to Hueco Mundo, where she presumably spent most of her life relentlessly fighting for survival against hundreds of cannibalistic monsters in a dimension she knew nothing about after forcing the still-barely alive hollow into submission. And keep in mind that, at the time, she was barely over the age of ten. The final kicker is that Homura was a genuinely likable and sympathetic character, even taking into account her [[Yandere]]/PsychoLesbian tendencies, which makes her death scene even more of a [[Tear Jerker]] than it already is.
** The arrancar Ulquiorra. He's stated to be the personification of Nihilism, is loyal to [[Complete Monster]] Aizen, considers Ichigo and all others below his power level little more than "trash", [[What Is This Thing You Call Love?|cannot comprehend things like love and friendship]], kidnaps Orihime and is very cold towards her, badly injures her friend Ishida's hand (cuts it off in the manga, breaks and burns it in the anime), and kills Ichigo in front of Orihime to prove a point to her. However, he seems to gradually soften up towards humanity thanks to his interactions with the captive Orihime, and Ichigo, too, to a lesser extent. He also regards the senseless killing done by other arrancars as childish, and is [[Even Evil Has Standards|disgusted]] when Nnoitra says that he should [[Rape Is a Special Kind of Evil|rape]] Orihime. His {{spoiler|death}} is also incredibly heartbreaking. It even seems like he is finally starting to understand human bonds, seeing how, in {{spoiler|his last moments, Ulquiorra reaches out to Orihime and asks her if she finds him frightening, mirroring their conversation before Ichigo arrives in the tower. She replies with tears in her eyes that she doesn't and reaches back for him, but his body dissolves before they can touch.}} Of course, however, fans go from considering him a [[Jerkass Woobie]] to [[Draco in Leather Pants|something else entirely.]]
*** His backstory in "Unmasked" also reveals that he never experienced happiness and that his hollow brothers/clan tried to eat him because he was different from them. Again, [[Draco in Leather Pants|don't forget that he is STILL a pretty creepy bastard when at his worst]]
** There's also Kaname Tousen, the only Captain to ever gets The Scrappy status, who betrays Soul Society for a hypocritical reason (going down the path with the least bloodshed by joining the Big Bad). His close friend was killed by her shinigami husband, after she scolded him for killing his comrade in battle. So, he joins up with Aizen, pretty much wants all the shinigami dead, and is willing to destroy a town full of people, all to get revenge on every single shinigami. After being beaten by his vice captain and being reminded of his errors by his best friend, Tousen seems to repent, cries, and wants to have one tender moment with his vice captain...and then blew up in front of his vice captain and best friend.
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** Saionji too. Yes, Saionji was a total [[Jerkass]], but not even he deserved Touga's horrible treatment and manipulation of him.
* ''[[Higurashi no Naku Koro Ni (Visual Novel)|Higurashi no Naku Koro Ni]]'':
** In the Watanagashi/Meakashi-hen arcs, {{spoiler|Shion Sonozaki}} pretty much fits the bill. On the one hand, there's everything that she has had to go through as [[The Unfavourite]] of her family, never mind the [[Cold -Blooded Torture]] she's put through just before she finds out about {{spoiler|her boyfriend Satoshi's disappearance}} -- which she had gone through specifically in order to ''prevent''. On the other hand, her [[Roaring Rampage of Revenge]] goes [[Ax Crazy|so far off the rails]] (specially in the case of {{spoiler|Satoko, whom she straps to a cross and tortures to death, and Mion, whom she forces to watch as she murders poor Satoko}}) that it's hard not to be relieved {{spoiler|when she finally gets her [[Karmic Death]] near the end}}, if only for her own sake.
** {{spoiler|Takano, to an extent. Growing up and being tortured into insanity in an [[Orphanage of Fear]] after the death of her parents after a massive traffic accident caused by [[Contrived Coincidence|the bus driver]] dying of a sudden heart attack, having her guardian's life's work trampled on by his colleagues [[Determinator|made her do everything to prove that the man who had cared for her wasn't full of shit.]]}} Possibly inverted by the time of ''[[Umineko no Naku Koro Ni (Visual Novel)|Umineko no Naku Koro Ni]]'', {{spoiler|when Lambdadelta said in the supplementary materials that Takano's goal, when she was a young child, was [[A God Am I|to become a god.]]}}
* ''[[Ooku (Manga)|Ooku]]'': Shogun Iemitsu the Younger (or [[She Is the King|Lady Chie]], depending on who you ask). We first see her when the former buddhist monk Arikoto is presented to her, given a 'maidenly' name, and ''beaten about the head and face'' '''by''' ''her until he bleeds, for not answering to it fast enough''. However, even without factoring in the [[Deus Angst Machina|improbable extent]] of her [[Dark and Troubled Past]], it becomes clear that she is, in truth, a prisoner in the Shogun's castle who has been stripped of both her name and, to a large degree, her gender as well. Not to mention the fact that the closest thing to love she gets {{spoiler|[[A Match Made in Stockholm|before Arikoto comes into the picture]]}} is from someone who she knows [[Loving a Shadow|only sees the reflection]] of [[Child By Rape|a father she never knew]] in her.
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* Arguably, [[Haruhi Suzumiya (Literature)|Haruhi Suzumiya]]. She learns, rather painfully, that she isn't all that special, and in her quest to make her life special, goes on a hunt for aliens, time travellers, and ESPers after some inspiration from Kyon. This leads to her general sociopathy and her obsession with cosplaying Mikuru. Kyon says that, through her [[Character Development]], she's not exactly turning into a good person, but is ''returning'' to be the kind kid she once used to be.
* Ayato Naoi of ''[[Angel Beats (Anime)|Angel Beats]]''. He's kind of a [[Jerkass]] to everyone, [[Ho Yay|except Otonashi]], but when alive, his brother was his father's apprentice in pottery, while he remained in his room, ignored by the world. Then his brother died and he had to take his place, but wasn't nearly as good at the craft as his brother. Having no choice but to live his life as someone else, he began to think that his entire life was a charade.
* ''[[Angel Sanctuary (Manga)|Angel Sanctuary]]'': [[Dysfunction Junction|Pick a character, any character]]. The entire freaking cast is full of [[The Woobie|woobies]] ({{spoiler|[[God Is Evil|save for God Himself]]}}), the overwhelming majority of which are [[Jerkass|jerkasses]] ''[[Black and Grey Morality|at best]]''. One character wins gold on both counts, however. Is it [[Brother -Sister Incest|Setsuna or Sarah]]? [[Unlucky Childhood Friend|Kurai]]? [[Noble Demon|Kato]]? [[Stalker With a Crush|Kira]]/[[Empathic Weapon|Nanatsusaya]]/{{spoiler|[[Because Destiny Says So|Lucifer]]}}? [[The Atoner|Zaphkiel]]? [[Unwitting Pawn|Raziel]]? [[I Just Want to Be Loved|Astarte]]/[[Sharing a Body|Astaroth]]? [[Broken Bird|Alexiel]]? [[Tragic Monster|Rosiel]]? [[Mad Love|Katan]]? [[All Love Is Unrequited|Belial]]? [[Can't Catch Up|Michael]]? [[The Unfavourite|Arachne]]? [[Lonely Rich Kid|Metatron]]? [[And I Must Scream|Sandalphon]]? No. Believe it or not, it's [[Evil Chancellor|Sevothtarte]]/{{spoiler|[[Break the Cutie|Lailah]]}}. {{spoiler|As an up-and-coming scientist, [[Shrinking Violet|Lailah]] was outshone ([[Unknown Rival|unintentionally]]) by [[The Ace|Anael]] in both work and love. When she finally rose in status, jealous co-workers [[Rape As Drama|raped]] [[Rape As Backstory|her]]. Though she murdered them and [[The Scapegoat|successfully blamed]] [[Love Martyr|Nidhogg]], [[No Sex Allowed|losing her virginity]] (even non-consensually) left her branded a [[Fallen Angel]]. [[Freak Out|Her entire world crashing around her]], Lailah [[Deal With the Devil|sold herself to Sandalphon]], taking a new face to [[Villainous Crossdresser|impersonate a dead male soldier]]. As Sevothtarte, Lailah became a Seraph, Chairman of [[Council of Angels|The High Council]] and caretaker of [[Regent for Life|Metatron]]. From there, Lailah tried to "purify" heaven of all sinful/deformed angels. However, [[The Hero|Setsuna]]'s interference and [[Evil Versus Evil|Rosiel's return]] [[Laser -Guided Karma|publicly]] [[Humiliation Conga|exposed her fraud]] and freed Sandalphon, who [[The Dog Bites Back|raped her]] and [[Villainous BSOD|destroyed her psyche completely]].}}
* Kevin of ''[[Karate Shoukoushi Kohinata Minoru (Manga)|Karate Shoukoushi Kohinata Minoru]]'' is established as one of these in chapter 66.
* Kuromi from ''[[Onegai My Melody (Anime)|Onegai My Melody]]'' may qualify, giving that the reason why she's acting like a jerk is because My Melody made her life miserable.
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* Akira from ''[[Togainu no Chi]]''.
* Lots of these show up in ''[[Fairy Tail (Manga)|Fairy Tail]]''. Looks like Hiro Mashima loves this trope.
** [[Knight of Cerebus|Gerard]] [[Used to Be A Sweet Kid|Fernandez]] (or Jellal, [[Spell My Name With an "S"|however you want to call him]]), Erza's childhood friend who, like her, was [[Made a Slave]] by a bunch of Zeref cultists who could charitably be called [[Complete Monster|Complete Monsters]], and ended up being locked up in a cell and tortured almost to death when he wasn't even in his double digits. Flash forward to the present time, and Gerard, after being possessed by Zeref himself, getting a well-deserved revenge against the slavers and having completed the Tower of Heaven, had cooked up a plan to create the "World of Magic" where everyone would be free...which would require mountains of corpses, the sacrifice of Erza herself, and, generally, screwing things up royally for anyone who wasn't magically gifted. He had gone through so much hell in his short life that he thought no sacrifice was too great if it would mean nobody would have suffer like him. {{spoiler|And just for grim irony, it turned out that his plan of reviving Zeref had no chance of succeeding from the very beginning, and that it wasn't Zeref who was speak to him}}. All in all, [[Base Breaker]] as he is, you can't deny that his life ''sucked''.
** [[Magnificent Bitch|Urtear]] [[Time Master|Milkovich]], [[Big Bad]] Hades' right hand woman {{spoiler|and the person responsible for Gerard's [[Start of Darkness]], since it was her who spoke to Gerard's mind, pretending to be Zeref}}, was revealed to be one as well at the end of the Tenrou Island arc. Want the lowdown? {{spoiler|When she was just an infant, she was separated from her mother Ur by a bunch of heartless scientists who wanted to use her for her immense magical potential. (Ur had asked for their help for her ill child. Those monsters took away the little girl and told her mother that Urtear had died from her fever and that her body was too horribly mangled for a mother to see.) Raised as little more than a sentient lab rat, Urtear was told that her mom had abandoned her and grew to resent her...but, most of all, she desired to go back in time to the moment of her abandonment and prevent it from coming to pass. In order to do so, she grew up into a brilliant and Machiavellian [[The Chessmaster|Chessmaster]] and [[Manipulative Bitch]] who would stop at nothing to awaken Zeref and uncover the World of Magic, confident that all her evil actions would be erased the moment she travelled back in time and averted the very event that sparked them.}} In the end, Urtear committed a lot of terrible things which were fueled by her desperate desire to {{spoiler|meet with her mother and achieve some happiness for herself. When her plan failed, she fell into such shame and depression over what she had become that she tried to commit suicide to atone...and, ironically enough, she was saved by her [[Morality Pet]], Meredy, a young girl Urtear had taken under her wing (after destroying her village...) and treated like a real daughter.}} Now, will someone please punch this woman in the face, and then give her a big hug?
* Suzu of ''[[Peacemaker Kurogane (Manga)|Peacemaker Kurogane]]''. Suzu becomes an insane [[Jerkass]] after he thinks that Tetsunosuke (his only friend) killed his master, Yoshida (whom he admired and was the only person who cared for him). Not to mention that he was taken in by a [[Depraved Homosexual]] old man and raped when he was alone and starving on the streets.
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* [[Cute Bruiser|Taiga Aisaka]] of ''[[Toradora (Light Novel)|Toradora]]''. Her violent emotional mood swings and stature complex stem more [[Parental Abandonment|from having a broken family]] than romantic issues, making her a borderline [[Broken Bird]].
* Michio Yuki of ''[[MW (Manga)|MW]]'' judging by his backstory of being kidnapped and {{spoiler|molested}} by a criminal who becomes a priest in the future. Does that end for him? No, he gets exposed to the titular chemical warfare that not only turns him into the villain that he is, [[Ill Girl|but also gives him occassional headaches, getting hospitalized at one time, and only has a few years left to live]]. You can't help but feel sorry for this guy even if [[Complete Monster|he's beyond redemption]].
* In [[Nausicaa of the Valley of The Wind (Manga)|Nausicaa of the Valley of The Wind]], Kushana, who is introduced in the film version as a seemingly steriotypical evil queen ("Nice valley. Think I'll keep it."), her status as an apparent [[Card -Carrying Villain]] is quickly subverted. This apparently was deliberate on the part of the writers: Miyazaki describes Nausicaa and Kushana as "two sides of the same coin", largely differing in that Kushana has "deep, physical wounds".
* ''[[Azumanga Daioh (Manga)|Azumanga Daioh]]'': [[Alternate Character Interpretation|If her dreams are any indication]], [[Inferiority Superiority Complex|Tomo has massive insecurities, which leads to her]] being such a [[Jerkass]].
* Rin from ''Kodomo No Jikan'', especially in the earlier volumes. Yes, she has had a rough childhood and clearly needs to be helped, but the way Rin behaves - ways that could get a basically innocent man sent to prison, or seriously hurt someone - is just nasty. And she knows it.
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