Being Evil Sucks

""I'm the bad guy! I don't save the day, I don't fly off into the sunset, and I don't get the girl! ...*sigh* I'm going home.""

- Megamind

It's good to be bad? Think again.

Despite what certain morally ambiguous personages would have you believe, being Evil isn't necessarily all it's cracked up to be. It can destroy you, your Soul, and everyone you love and care about. Sure, evil may be temporarily satisfying, and man, it sure bakes good cookies, but cookies are unhealthy and fattening, and once those cookies are gone, what do you have left once you've given up everything just for that tasty, tasty murder, uh, I mean treat...

The thing is, you may enjoy yourself for a little while, but eventually it will come back to haunt you in unpleasant ways. Kicking the morality pet has the unfortunate side effect of making you lose sleep at night or consuming you with guilt over the horrible things you've done. Letting your anger rule you is fun and easy... but you'll probably Kick the Wrong Dog in your bloodlust. Oh yeah, and there's also the likely chance that you will go mad, which really isn't as cool as it sounds when you're in a straitjacket.

Because, you see, true happiness can only be achieved through The Power of Love or the Power of Friendship. Anybody can cross the Moral Event Horizon, but once you're there it looks pretty bleak. Nobody wants to be your friend because they're all terrified that you'll kill them in their sleep (or you already have), you've done nothing to better your position except cause more suffering and generally made the world a worse place to live in. And through it all you've nourished so many bad feelings that not even Evil Feels Good anymore, you don't even remember what it's like to feel good for a change.

Of course, such a change of heart can be made much harder if it turns out Being Good Sucks, too. This is the likely reason behind many a Heel Face Turn, and may result in The Atoner or an Anti-Villain; it is a staple of almost every Tragic Villain. Even if the villain doesn't turn from his evil ways, having him realize this can make him much more sympathetic, and it can be rather tragic when the Well-Intentioned Extremist reaches the point where he realizes that he's not the good guy after all.

Compare Ineffectual Sympathetic Villain and This Is Your Brain on Evil. Being evil can be even worse when you're bad at it.

Anime and Manga

 * General Regius Gaiz of Magical Girl Lyrical Nanoha StrikerS. After years as a corrupt official, guilt came knocking at his door in the form of Zest, his best friend who shared his dreams of justice . Once he learned about his return, the formerly pompous general spent his time sitting in his desk in a defeated state, waiting for Zest to come.
 * Gaara of from the series Naruto doesn't quite realize this until he gets the snot kicked out of him by Naruto in full "I fight for my friends" mode.
 * In Code Geass, Lelouch finds out that being evil tends to get karma screwing you over, and
 * Light Yagami of Death Note, who starts out as a normal yet highly intelligent high schooler who could truly make a difference in the world in a positive way, but also has too much free time on his hands. That is until he finds the Death Note, which at first he claims to use only on irredeemable criminals under the alias "Kira". He quickly comes to use it to kill off anyone who gets to close to uncovering the truth or questions his motivations. He grows progressively more paranoid and unhinged, jumping of the moral slippery slope as he tries to ensure Ryuk doesn't grow too bored (who will kill him otherwise) and manipulates just about everyone he knows including his own family to serve his ends. It all comes to a head at the end of the series,

Comic Books

 * in Watchmen. His intentions, of course, were never entirely evil; he wanted to stop World War III before it started, and
 * Also, half of The Comedian's mental background comes from this.
 * Unsurprisingly, Golgoth finds this out early on in Empire. However, by the end
 * Spider-Man's enemy the Sandman eventually got sick of all the grief that came of being a criminal, and tried to go straight. He stayed a good guy for twenty years, real world time (just a couple of years, comic book time). Then his old evil teammate the Wizard stuck him in a brainwashing machine to make him evil again, causing him more grief. Poor dude.
 * Superhero team the Thunderbolts was founded as a front for a group of supervillains to gain the trust of the world's various peace-keeping forces in preparation for a world domination scheme, by changing their identities and pretending to be heroes. At least half the original team members came to realize that they really liked not being feared and hated and decided to give up on world domination and remain good guys.
 * Superhero team the Thunderbolts was founded as a front for a group of supervillains to gain the trust of the world's various peace-keeping forces in preparation for a world domination scheme, by changing their identities and pretending to be heroes. At least half the original team members came to realize that they really liked not being feared and hated and decided to give up on world domination and remain good guys.

Fanfic

 * In the BLoSC Fan Verse of For Good, Warp Darkmatter holds this opinion beneath his front of Evil Pays Better. It's a crucial factor in his eventual Heel Face Turn.

Film
""And I kept asking myself all the time, how did I buy into this shit? It was because I was pissed off, and nothing I ever did ever took that feeling away. I killed two guys, Danny, I killed them. And it didn't make me feel any different. It just got me more lost and I'm tired of being pissed off, Danny. I'm just tired of it.""
 * American History X has Derek turning away from his neo-Nazi lifestyle as he realizes how unhappy and basically crappy it has made his life:

""Calling someone else fat won't make you any skinnier. Calling someone else stupid doesn't make you smarter. And ruining Regina George's life certainly didn't make mine any happier.""
 * This is the lesson Cady learns at the end of Mean Girls.

"I look at my red hands and my mean face, and I wonder about that man that's gone so wrong."
 * In Battle Beyond the Stars, Roger Corman's Magnificent 7 In Space, one of the recruits is the galaxy's greatest assassin. He's amassed great wealth, but he muses that he lives alone and bored because he's feared everywhere he goes. The kid promises a home on his planet where no one knows him and where he can be happy if he helps them fight off the slaver.
 * Lucy Diamond in D.E.B.S.. After she falls in love with Amy and realizes that she'll have to give up her life of crime to be with her, she says "Being bad doesn't feel good anymore."
 * Star Wars: Anakin's turn to the dark side costs him everything and everyone that he loves as well as leaves him locked in a robotic life-support system.
 * Michael Corleone in The Godfather is one of the best examples. He was a likable young man who could have done a lot of good in the world. But somehow he made the wrong choice, partly through upbringing. And partly through focusing too much on loyalty. And partly because while he always wants to do a Heel Face Turn and comes close on a couple of occasions (as with his talk with the future Pope), he can't bring himself to give up wealth and power. He was very good at being evil but something inside him always seemed to consider that the worst fate of all.
 * He always justifies his actions as being done for the wellbeing of his family but by the end of the second movie he starts to realize that they have actually destroyed his family. By the end of the third movie almost all the people he cared for are dead as a result of his choices.
 * This is the point of any Mafia stories that we can bring up, although they tend to be very cynical in nature. Scarface, for example.
 * As the massive Misaimed Fandom shows, Scarface also frequently intertwines this with Evil Is Cool.
 * Subverted (somewhat) with Goodfellas. Henry Hill's life of crime ultimately leaves him in the witness protection program, divorced and living his life as (in his own words) a "schmuck". And he knows very well the alternative was death. But the final monologue of the movie is Hill pining for the old days of crime, wealth and excitement.
 * The eponymous character in The Assassination of Jesse James qualifies for this. The myth around him has developed to the point where he finds it impossible to escape it and he is constantly reminded of the consequences of what he has done. While he is an unstable bully, he feels genuine remorse for all the lives he has taken and wants nothing more than death. Beautifully summed up by his line:


 * Lord Shen in Kung Fu Panda 2 is haunted by the perception that his parents hated him, and now is out to conquer Gongman City and then China to have something worthwhile in his life. However when pressed, even he can't say whether his dream is worth anything other than an excuse to kill anyone in his path.

Literature
"He wouldn't be able to walk on a street on any civilized planet in the galaxy; people wouldn't be able to abide his presence. Nor would he blame them. He couldn't stop thinking about it. He didn't believe he would ever be able to stop thinking about it. The dead would haunt him, forever. How could a man live with that?"
 * A Series of Unfortunate Events For the first few books, it seems Count Olaf will always win, but slowly we realize that he alienated the one person he loved and lost practically all his henchman, all on the hopes of getting the Baudelaire fortune. Guess how well that worked out?
 * Harry Potter:
 * Severus Snape: All of his years devoted to the dark side eventually gained him nothing but destroying the one thing he'd ever loved, although  didn't really seem to do anything to improve his happiness. But he did spend the rest of his life trying to atone for  . In other words, being Snape sucks.
 * Draco Malfoy learns this the hard way near the end of the series. There's a big difference between idolizing a "cool" Evil Overlord from a safe distance and being ordered by said overlord to commit murder with the threat of having your entire family killed. Draco also finds out that he really doesn't have it in him to directly kill a defenseless person right in front of him. In Book 7 he learns that he doesn't enjoy inflicting Cold-Blooded Torture.
 * Also Voldemort himself who is completely uncapable of feeling love. he is driven solely on ambition and greed, and does everything he can to ensure that he'll live forever,  Its also shown that Being Evil Sucks for his followers as well who are under the constant threat of being murdered by him if they try his patience in any way. And once they're in, they're in for life.
 * In Death Star, the gunner who fired the superlaser that destroyed Alderaan, who had always wanted to fire the biggest gun, finds that following orders and actually getting what he'd wished for led to misery beyond his wildest dreams, a personal Moral Event Horizon. He can't justify it, can't either make it less of a crime or blame someone else, and is unable to sleep for guilt and horrible dreams. When the Death Star is in range of Yavin he stalls desperately, hoping that something would happen and he wouldn't have to pull that trigger again. He got that wish.


 * While the Dark Ones in Night Watch use every opportunity to brag about all that freedom, independence and strength The Darkness had given them and to make some lenient remarks on the poor deluded Light Ones who are so very constricted by their rules and who fuss over humans so much... It turns out that vampires are haunted by persistent insatiable Horror Hunger, werewolves have to deal with feats of feral uncontrollable rage once in a while and all the Dark Ones in general live in a world of constant paranoia and distrust towards their own brethren and superiors. Especially superiors who wouldn't even bother notifying that You Have Outlived Your Usefulness before they set up and sacrifice you as a part of their Evil Plan.
 * Considering that the Light Ones aren't much better (Light One attempts at "social engineering" caused both Hitler and Stalin), and that the Light One commander-in-chief Gezar basically only hasn't given in to suicide because he is so used to scheming all the time that he doesn't know how to do anything else, you could also consider this a very Russian commentary on the evils of bureaucracy and the Cold War. No veteran member of either of the Watches is ever portrayed as genuinely happy with their life, while the one non-Watch dark magician we see is shown enjoying himself in a restaurant with his lovely wife and happy children.
 * After Edmund Pevensie gets captured by the White Witch, he realizes that satisfying his greed wasn't worth the consequences it entailed for Narnia and his siblings.
 * This is pretty much the whole thing about vampires. Sure, you'll remain young for all eternity, but in due time life will lose its thrill, and you've seen your last sunrise as well. Both metaphorically AND literarily speaking. You'll have some really neat super powers, too, possibly including, but considering the fact that all vampires are different, most likely not limited to: Super Strength, Super Speed, Shapeshifting, Nigh Invulnerability and Flight. But the primary thing that you will use these amazing abilities for is hunting down other humans in order to sustain your accursed life.

Finally, the cruncher: while you may feel emotionally dead, there is still a fairly good chance of you finding your one true love. But bear in mind that said person is also your food. Thus, each time you see his/her exposed neck, you will feel the urge to bite him/her, an act that may curse him/her with the same disease that turned your life into a Fate Worse Than Death (well, unless you're a Succubus that is, in which case you have a rather different way of taking in nourishment. A process which will almost certainly outright kill your significant other. Consequently, you Can't Have Sex Ever). The alternative is either leaving your beloved before anything bad can happen, or, through The Power of Love, resisting the urge... Only to see your loved one grow old and wither away in front of your very eyes. Conclusion: Being a vampire sucks.

It should be noted that in recent years vampires in literature have gone from 'cursed' to 'you, only better than you will ever be', with no real downsides that come close to outweighing the benefits. They've also by and large swapped being villains or antiheroes for being Boring Invincible Heroes. Twilight is, of course, the worst offender and most well known. "What do I fear? myself? there's none else by: Richard loves Richard; that is, I am I. Is there a murderer here? No. Yes, I am: Then fly. What, from myself? Great reason why: Lest I revenge. What, myself upon myself? Alack. I love myself. Wherefore? for any good That I myself have done unto myself? O, no! alas, I rather hate myself For hateful deeds committed by myself!"
 * More recently, in other genres, vampires are often portrayed as Black Mages.
 * Raistlin Majere at the end of the Dragonlance Legends trilogy.
 * This is the overarching meta-theme in Middle-Earth. Evil consumes all it touches, leading them to waste their lives before their miserable deaths. This is true from the first Dark Lord Morgoth to mortals to Sauron to Saruman. Everyone who gives in to darkness ends up bitterly regretting it, and that's if they're lucky. If they're not, it's And I Must Scream time.
 * You also see this in Shakespeare's Richard III, where at the beginning Richard says, "I am determined to prove a villain / And hate the idle pleasures of these days." At the end of the play, he remarks to himself:


 * In the book version of The Talented Mr. Ripley, Ripley gets away with everything. On the other hand, Ripley spends the rest of his life in paranoid fear of the police, wondering if the next cop he sees has figured out what Ripley has done.
 * Sisterhood series by Fern Michaels: Roland Sullivan in Lethal Justice learned this the hard way. However, it is does not cause him to Heel Face Turn...possibly because he's too spineless and weak to do it.
 * A Song of Ice and Fire has . After he , he thinks everyone he betrayed would stay his friends and accept him as their new leader. Instead, he gets 0% Approval Rating. Crossing the Moral Event Horizon   doesn't help his cause either.

Live Action TV
"Harmony: Being a vampire sucks."
 * Buffy the Vampire Slayer - "Selfless". The whole point of that episode was to show how damaged Anya was following her return to vengeance.
 * Even soulless vampires are sometimes subject to this—if, like Harmony or chipped Spike, they're Ineffectual enough to be aware that they're Ineffectual. Harmony flat out says it in season four:

"Mitchell: Well, there are downsides to working for a super-villain."
 * When Faith returns in Season Four it's clear that her hostility is accompanied by deep self-loathing of what she's become. She seemed to be happier with it prior to her awakening, but this is likely because her slide into darkness went in hand with her relationship with her father figure. With him dead all she had left was the knowledge of how badly she'd fallen. Immediately after she leaves the season, she shows up in the first season of Angel attempting Suicide by Cop, but thankfully ends up with a Heel Face Turn instead.
 * The fact that ex-demon Cole in Charmed managed to amass enough demonic power to become Nigh Invulnerable is the main reason that Phoebe divorced him (as he had become a threat to her and her sisters); particularly tragic as he'd only done all of that so he could escape hell to return to her. He couldn't even kill himself from the resulting grief.
 * Mentioned by Mitchell in one episode of Stargate SG-1 after they've captured a Mook and promised him protection from the bad guys. Sam points out that "protection" will mean locking him up:


 * Tony's psychiatrist on The Sopranos frequently hints that Tony's (and certain people around him) mental problems are due to this.
 * Walt in Breaking Bad, because of his meth-cooking, his wife wants to divorce him and he has been racked with guilt over the the results of his actions.
 * An interesting version occurs in Supernatural: apparently Hell sucks even for demons.
 * Er, yeah. Lucifer wasn't sent down there because he was a nice guy, you know! He was sent there because he didn't follow his fathers orders to cherish a, in his eyes inferior, species.
 * Heroes:
 * Well, given that the name of the volume was 'Redemption'...
 * In Kamen Rider OOO
 * In Power Rangers Samurai, Dayu made a Deal with the Devil but didn't get what she asked for in the way she wanted (devils are like that.) By this point, she's sick of being The Dragon to Master Xandred but there's no way out. However, she's no friendlier to the Rangers, at least not yet.

Music
"It gets so lonely being evil. What I'd do to see a smile... even for a little while. And no one loves you when you're evil... [Beat] I'm lying through my teeth! Your tears are all the company I need."
 * Subverted in Voltaire's song "When You're Evil". The last verse sounds almost like the singer is bothered by his villainous ways and longs for some human happiness... 'Almost' being the key word here:


 * Huh. I always figured it was played straight, and that the last two lines refer to the rest of the song.
 * Either that, or it's himself he's lying to.
 * But then there's the "your tears are all the company I need" part.
 * The Who's "Behind Blue Eyes," which was intended to be a song for the villain of Lifehouse, the album that became Who's Next.

Religion/Mythology

 * The original and most ancient concept of Karma, before later doctrines, meant action. Hence, doing anything inherently created a new 'self' which was different. Grossly oversimplified, the first victim of wrongdoing is yourself, since you've made yourself into something less than you were.
 * Similarly, in Christianity and Islam, the wages of sin are death, a weakening of your relationship with God, and eventual damnation if not repented.
 * Satan himself is supposed to be constantly tortured by his decision. The Divine Comedy even has him.

Tabletop Games

 * In the World of Darkness, you just can't win. Not only does being good suck, but if you decide to go the other way and embrace the dark side, you can look forward to a number of side effects - starting with batshit insanity. Each of the game lines comes with its own drawbacks, lovingly crafted to screw with that particular type of critter.
 * Vampires: Stronger predatory instincts and a thinner veneer of humanity, meaning the human prey can sense you want to eat them. This tends to make them want to stay away. But wait, that's not all. You're literally going to devolve into a mindless animal if you do enough evil. And moreover your new society consists of assholes and psychopaths, most of whom are way older and more powerful than you and there is that mutual risk of flipping out and killing each other whenever you first meet another vampire. The original Vampire doesn't let you off the hook lightly either. While meetings between two groups of vampires do not devolve into brawls every time, you're still stuck in the society of manipulative monsters, and the power difference between you and the Powers That Be is much greater.
 * ...Unless you happen to be a member of Belial's Brood. Their sacred rites literally make it impossible for them to betray each other, and they just don't care about being human, so that's also a non-issue. Also, if you're subtle enough with your Vice, there's a chance that the transformation into a dragur will not take your mind with it, although you're still a massive dick.
 * Werewolves: The spirits you're trying to police can tell you're out of balance, and they hate you that much more. You have a harder time performing rituals, and it's that much harder to keep from kill-everything-around-you berserker rage. On top of all that, you tend to develop disturbing obsessions - from breaking every third window you pass to taking a bite out of anyone who looks you in the eye. In the original Werewolf you suffer nothing of the sort and can techically do anything you please. There is just that little problem with the Universe-devouring Big Bad who has a Fate Worse Than Death in store for your entire race and you personally, and whose local representatives are generally empowered by evil acts.
 * Mages: You know that Abyss that hates your magic? The more evil you become, the harder it can smack you around and the harder it is for you to resist it. In the original, you're pretty much free to do as you wish; thing is, there's a horde of Eldritch Abominations seeking to drag reality down into oblivion with them, and their goals are furthered by the spread of evil.
 * Prometheans: You know that whole "I wanna be a real boy" thing you've got going on? Yeah, well, your ability to comprehend humanity is judged in part by how much you understand human morals. You can be a mad murdering monster, but good luck ever earning a soul that way. Oh, and if you want to create a kid/companion like you who'll help you deal with the loneliness, there's a much better chance the process will go horribly wrong and result in the creation of a bunch of cannibalistic aberrations that wish to devour your essence.
 * Changelings: A double-dose of insanity; not only do you suffer specific derangements, but your perceptions are more and more skewed by your Fae experiences. Plus, you become more and more like one of the Fae overlords who kidnapped you.
 * Hunters: One trope: He Who Fights Monsters. And that goes for the previous game, too.
 * Demons: To start, you just spent human history in a Hell far worse than humans comprehend. you get out, but the more evil you grow, the more Torment you accumulate, until eventually you become an Earthbound, an Eldritch Abomination without anything resembling sanity. And God will never forgive you in any event.
 * Sin-Eaters: You find it harder and harder to enter and navigate the Underworld. Kerberoi and geists can tell you're out of sync with your geist, and become more reluctant to deal with you. You also find it more difficult to perform ceremonies. Hit absolute bottom, and you end up as a Meat Puppet for your geist to drag around.
 * Wraiths: Your Shadow, your resident Enemy Within, grows more and more powerful, working against everything you care about. When it's finally able to take over, you become one of the local servants of Oblivion, and now work to the destruction of everything.
 * Geniuses: (yes, it's fanmade, but shut up): the you that's actually, well, you slowly dissipates and your personality is overtaken by some strange, unknown and terrifying will that leads you to horrible acts. Also, the Geniuses who haven't given in to Illumination (likely including your friends and Mentor) will hunt you down and kill you. Granted, at that point it could be considered a mercy to you.
 * The fate of most servants of Chaos in Warhammer Fantasy Battle and Warhammer 40000. Sure, the lucky few become immortal and godlike Daemon Princes, but the vast majority is doomed to become consumed by their emotions and end up as blood-crazed berserkers who live only to kill and die in battle, jaded hedonists who have to keep doing more and more depraved things simply to feel something, sorceress who are forever driven to expand their knowledge in an attempt to reach an impossible goal, or disease-ridden husks who are kept alive by supernatural powers despite their bodies rotting away. That is, if you don't simply end up becoming a mindless mass of betentacled gribblyness because of all the mutations you've been receiving, or simply sacrificed, as cannon fodder, as an experiment, to slate the hunger of ravenous daemons, as a sex toy to rapacious daemons, or simply For the Evulz.
 * Do enough truly evil stuff in Ravenloft and you'll end up becoming a darklord, along with the requisite powers and your own domain. Sounds fun, right? Except that you're confined to to your realm, you're forever being tormented by the objects of your desire, and the only way to escape is through a Heel Realization. Of course, as the sourcebook states, if you were the kind of person to ever have a Heel Realization, you probably wouldn't have become a darklord in the first place.

Theater

 * Several villains in Shakespeare plays find this out. Macbeth and his wife find that killing the king so that you can inherit the throne wasn't worth it, and Claudius also ends up learning that same lesson.

Video Games

 * in Neverwinter Nights turned to the dark side to get vengeance fully understanding that being evil sucks, and counted on the fact that her boss would betray her and kill her because she felt she deserved death for turning in the first place.
 * Being evil for Darth Nihilus in Knights of the Old Republic really sucked, as indulging his supernatural hunger ate him away from the inside.
 * So you are saying he got "sucked" to death?
 * BioWare used to run with this in general. In both Jade Empire and Knights of the Old Republic, taking the dark path means you'll end up having to slaughter most of your party, delivering a Player Punch and making the endgame more difficult.
 * in The World Ends With You. As a result of.
 * Sephiroth has power beyond what anyone can imagine but at the expense of his sanity, memories, emotions and very humanity.
 * While in the original Final Fantasy VI, Kefka was painted as a psychopath without remorse, restrains or regrets who actively, and successfully, tried to make every bad situation much, much worse, all of it because he found it entertaining beyond reason, the developers for Dissidia Final Fantasy decided to run with an Alternative Character Interpretation. There he is instead depicted as a man who's nigh-godlike powers have ruined his ability to feel joy to the point where he can only feel it when destruction is involved. The reprise of his well-known, hateful, nihilistic rant about the futility of the world from the original game takes on the nature of a wistful lament, and even as Kefka dies, he laughs. A sad laugh.

Visual Novels

 * Kotomine in Fate/stay night discovered a long time ago that Being Good Sucks but kept trying anyway. After all, even if it brought him no satisfaction he did have a moral compass. And then his Ill Girl of a wife died and he had a chat with Gilgamesh and decided to be evil instead. By the time the story starts, Being Good Sucks and Being Evil Sucks and it pisses him off so much Basically: If being good is supposed to be a good thing, why doesn't he like it? If he should just be evil, why does that feel wrong to him?

Web Comics

 * Trudy of General Protection Fault loves Nick, but her scheming to take over the world and using him in those schemes ultimately drives him to reject her. In the Bad Future, this leads to her killing him, losing her sanity in the process and hunting down the rebels to "avenge" his death. In what actually happens, she tries to kill him, but is unable to go through with it, and ends up on the run, tormented by dreams of guilt about her actions and by Nick's last disappointed look toward her. After Nick and Ki get engaged, she slips past the Despair Event Horizon and once attempts suicide, but meeting Akhilesh enables her to come to terms with herself and work more toward atoning for what she has done.
 * As the Fuchsia Succubus begins to see.
 * During the "Court of Karnak" arc in Dominic Deegan, Karnak and Bulgak both realize that reigning in Hell is utterly meaningless—no one truly rules Hell. They are all prisoners.
 * Bulgak responds by renouncing his old, selfish, egotistical self, which releases his essence back into the world. Karnak simply appoints himself warden.
 * Alt-Schlock in Sluggy Freelance learned this far far too late after he'd eliminated nearly all of humanity and created a Crapsack World of only one city who's few remaining citizens are living drug addled lives with no memories and that the only way to maintain it will slowly destroy what's left. He finally shuts off the nano machines keeping himself alive because he's lost everything and doesn't even want to live anymore. Schlock prime is heading in the same direction.

Web Original
"Voldemort: Killing people doesn't make them like you, it just, it just makes them dead."
 * The Order of the Stick prequel book Start of Darkness details the origins of Xykon and Redcloak. Redcloak eventually learns how much being evil sucks after Xykon makes him.
 * Doctor Horribles Sing Along Blog.
 * A Very Potter Musical has this gem:

Western Animation

 * The Batman: In the episode "The Apprentice", a kid in Barbara Gordon's class falls in with the Joker. Both have a weird sense of humor, and Joker makes him his sidekick as a mock to Batman and Batgirl. However, when they succeed against the caped duo and the Joker tells him to kill Batgirl, the kid is horrified. He just wanted to make a statement and defy convention, not kill. He wisely bails and the now favorable odds let the heroes beat the Joker.
 * This is essentially the reason for Dinobot switching sides during the first story of Beast Wars.
 * Actually, he thought Megatron had screwed up big time and so challenged him for leadership. When that didn't work, he challenged Optimus Primal to a fight to the death. Dinobot would have lost, but Primal spared him, so Dinobot joined the Maximals for his own honour. But he did eventually realise being evil sucks, leading the greatest CMOA ever.
 * In Avatar: The Last Airbender, Zuko realizes,, that despite having everything he ever wanted, he is dissatisfied with the methods he used to get there.
 * Similarly, Zuko's sister Azula learns the hard way that being a Magnificent Bastard may get you all the power and success in the world, but it also means that everyone around you is only there because they're scared of you or were manipulated into it. Unlike Zuko, Azula's pride won't let her admit that she was wrong; the resulting conflict pretty much destroys her mind, though Word of God claims that it's not totally beyond repair.
 * South Park, in the "Woodland Critter Christmas" episode, Kyle willingly takes the Antichrist's essence into his body, but immediately feels the excruciating pain of "having one's soul on fire". Stan replies with "what did you expect, dude, he's the son of the devil!" "Yeah, but I didn't think it'd be so... dark and evil!"
 * In the Bravestarr episode "Brother's Keeper," Bravestarr captures one of a pair of bandits who are brothers. The bandit admits the life of crime sucked and he's glad it's over, and the only reason he'd kept on with it was to look out for his brother, who is a much more unrepentant low-life.
 * In the Batman Beyond episode "Joyride", one Jokerz initiate tags along as another member of the gang hijacks an experimental advanced fighter craft. He becomes increasingly horrified as the hijacker goes mad with power and does things like attacking a rival gang armed with nothing but chains and tasers. When he overhears the guy denouncing the Jokerz as a crutch and ignoring Terry's warnings that's the last straw. He knocks down the lunatic with a folding chair and leaves the Jokerz forever.

Real Life

 * Alexis de Toqueville once met a plantation owner who had impregnated several of his slaves and was surprised to learn that by a quirk in the local law he could not free them: Which meant that he had to live knowing that his own children would grow up as slaves.
 * This was actually a common practice amoung slaveowners, at least in the U.S. Most slaveowners, however, just thought "hey, free slaves".
 * It was highly frowned upon for a reason. Despite it being a major reason for the Civil War, the practice was starting to decline, largely due to diplomatic pressure.
 * In general, after committing a crime, especially major ones, there is always the worry of getting caught and making enemies that are willing to make your life a living hell, or just outright kill you. You can become paranoid even if nothing is actually happening because there is always the chance of it really happening. And of course, general jail life is boring and dangerous. You never know when someone could rape or kill you in turn. Not to mention, even after the long prison term is over, you essentially HAVE to continue living as a criminal because there is now a document of your actions sent to every employer that might have given you a second chance at life even if you did turn over a new leaf. It's extremely, extremely rare for someone sent to prison twice for major crimes to ever have a chance at freedom (of any amount) and happiness again.
 * One additional problem is illegal money. While it is relatively easy to get away with the actual crime, good luck getting away with the money without being targeted by the IRS.
 * A story told once personally was about a crime boss in Philadelphia. A young man wanted for all the world to see him up close. So his friends took him to a club where the man spent his evenings. He was thin and pale, and spent the entire night chain smoking and looking around the room for enemies. The impression it left on the young man was life changing enough for him to pass it on to another.