Perhaps Rousseau was onto something, and no human being is really happy being evil. Or at least some people are unfit for a life of villainy. Rather than being a construct of pure evil, a villain can be a surprisingly normal person despite the tragic flaws and obsessions driving him to hatred and madness. He may even manage to have admirable qualities, becoming a sympathetic Anti-Villain. Along comes a chance at salvation: a skilled plastic surgeon, an influential psychiatrist, a doctor with a miracle cure, or maybe just an old friend. With that person's help, the villain manages to overcome his madness and look forward to some semblance of a happy and productive normal life.
However, something eventually goes wrong. Maybe they start having blackouts, and can't remember what they've been doing. Maybe they get visited by an old comrade who forces them back into crime. The voices in their head may resume their chorus. Or maybe they see their old nemesis and just have to test them, for old times sake... Ultimately, their returning obsessions become too much, and they can't resist them any more. They give in, and they eventually fall back into their self-destructive, villainous lifestyle.
If done right, it's Tragedy. If done wrong, it seems like an Ass Pull. The likelihood that the writer's attempt falls flat is greater when the real reason for villain's relapse is not the result of an honest artistic decision, but is merely catering to the demands of Status Quo Is God. A sadistic god indeed, who will never, ever allow the villain redemption, no matter how many times he tries during the series' long, long run and many spinoffs, it will forever remain a Tragic Dream. Chronic Villainy is perhaps the uglier, viler twin to Joker Immunity.
Compare Reformed, but Rejected, where the villain has repented and wants to go straight, but may find that the hero, or society in general, doesn't trust him enough to let him. Indeed, a particularly bad case of Reformed But Rejected can easily fuel a case of Chronic Villainy. A Self-Fulfilling Prophecy, courtesy of What the Hell, Hero? or All of the Other Reindeer. Compare also Redemption Failure, where the villain is pushed back to The Dark Side not by internal residue compulsions, but by external circumstances. Also compare Just a Gangster, where a criminal of some kind resists attempts to make them or their business legitimate.
Contrast The Farmer and the Viper, where a villain is given this same opportunity...and twists that goodness into a torment for the one who offered them redemption. Often, villains who try (and fail) to reform have some Idiosyncrazy.
This is not a villain who only pretends to reform and settle down; see Falsely Reformed Villain for that.
Note that those with the opposite affliction, Chronic Hero Syndrome, rarely suffer as much angst over it.
- Pokémon has Team Rocket. The trio are mostly Punch Clock Villains, and there are many times that they are able to start their own legitimate business. But they are still compelled to do their old job of stealing Pokémon, or something related to Pokémon, no matter how puny or mundane it maybe.
- Though the Saiyan race was described throughout Dragon Ball Z as Always Chaotic Evil, Shenron in Dragon Ball Z: Battle of Gods and Dragon Ball Super reveals that a group of ancient Saiyans tired of their race's villainy, and defeated them with the first Super Saiyan God. Of course, it wasn't long before the race returned to their Blood Knight ways even before Frieza showed up.
I've got you now, Joker. Heaven help me...I've got you.
- The Crown Prince of this is The Riddler, who has reformed countless times, only to fall back into crime due to obsessing over beating the Bat. However, this trope still applies to a large portion of Batman's rogues gallery, most prominently, Two-Face (who is probably a close second to the Riddler), The Ventriloquist, Mr. Freeze, and Harley Quinn. The second version, of a character whose power makes them evil and slowly returns them to villainy, is present in Man Bat and certain incarnations of Clayface.
- One comic book for The Batman animated series had The Riddler asking Batman for help, because the Joker had kidnapped his favorite staff member at Arkham. But The Riddler couldn't just ask, he sent riddles, because he has a compulsion to do so, whether committing crimes or not.
- This compulsion goes all the way back to the 1960's Adam West Batman (1966) tv show. In one episode, Riddler's girlfriend asks him why he even bothers with riddles since Batman always figures them out. Riddler answers that the only reason he even became a criminal is so he could use riddles to stump Batman. Without riddles, he says, crime would be pointless.
- A reviewer of the Batman series once went to the point of calling it nigh-Calvinistic.
- The Joker underwent a Riddler Reform in "Going Sane", a Story Arc from the comic Batman: Legends of the Dark Knight. The only times where he's ever been indicated to reform are when he thinks Batman's dead.
- As such, Batman: The Animated Series had a couple of these. There was a noirish episode involving Two-Face in which this was the Twist Ending, and one involving The Riddler (aptly named "Riddler's Reform", the original suggested title for this trope) in which he gave up a fortune because he couldn't get past his obsessions.
- The live-action Gotham has provided a new explanation on the Riddler's compulsion: while Edward Nygma has a fascination and fixation on puzzles and riddles and complex plans, he's able to turn it off when necessary. His real addiction is that he's an adrenaline junkie and realizes he gets a high off of nearly getting caught. Given his obvious genius, how better to ensure that people not as smart nearly catch him? Leave clues and hints behind.
- And in an episode of Batman Beyond, Mr. Freeze winds up as a particularly tragic example after spending most of the episode Reformed, but Rejected. (What's particularly tragic about that episode is that he gets a human body, and for no explicable reason, gets his ice powers back. However, Mr. Freeze has a history of tragedy in the DCAU, and while his backstory gave him depth, his later appearances in the The New Batman Adventures made him a bit of a Butt-Monkey.)
- In Batman & Mr. Freeze: Sub-Zero, his wife is revived and cured of her illness. What happens? It turns out his body is rapidly decaying, and soon, all that's left of him is his head.
- Harley Quinn got such an episode (appropriately called Mad Love). Over the course of it, she gets better, and finally realizes that the Joker doesn't care about her (after being left for dead by him) but sees a card that says "Get well soon - J" and instantly snaps back. (If you know the character, it's not an Ass Pull.)
- The Cluemaster, a minor Batman villain compelled to leave clues at the scenes of his crimes, was one of Arkham's few success stories. Unfortunately, he was cured of the compulsion to leave clues behind, not of a desire to steal things. His main claim to fame is being the father of Stephanie Brown, aka Spoiler / Robin / Batgirl / Spoiler.
- The Chronic Villainy of Batman's Rogues Gallery is justified by the common factor that almost all of them share: complete insanity. In their cases, villainy is almost their mental illness, one that seems impossible to remove. This is especially evident in Batman: The Dark Knight Returns, where both the Joker and Two Face go through apparent, but non-permanent, reforms.
- But then, even the Penguin, often regarded as the Only Sane Man among his enemies, had this once. In a two-part story (released as homage to the late Burgess Meredith) Cobblepot got restless and bored in his current role as The Don, and despite having vowed to stop getting involved personally, undertook a series of crimes just to prove he was superior to Batman. He failed, but convinced Batman to let him go (as he'd likely be let Off on a Technicality if arrested), and decided to go "back to my lounge booth - where I should have stayed."
- A major theme of more modern Batman comics is that Bruce Wayne may not be much saner than his rogues' gallery, meaning that he has a heroic version of this that isn't Chronic Hero Syndrome (which is about righting every wrong you're presented with, rather than being unable to give up running about all night punching people). This is most notable in the "Going Sane" arc, in which the Joker disappeared from sight at about the same time that Batman did. Bruce, who has recovered in a small town and has been striking up a romance with the woman who nursed him back to health, returns to Gotham, hoping against hope that he won't find any trace of the Joker and can return there. Then he digs into local video rental store records and finds a lot of classic comedies being rented by a "Joseph Kerr". He actually finds this rather upsetting.
- Many enemies of The Flash who are genuinely insane have gone through this, most prominently, Wally West's ex-girlfriend, Magenta (another case of psychotic power). Pyromaniac recidivist Heat Wave went straight with a federal job...but he burnt down a bar he went to after leaving the office. (Frustratingly, this came after a pretty lengthy period of nonvillainy—the character has been straight for nearly as long as he's been a criminal.)
- One Silver Age story had Abra Kadabra brainwash the governor into pardoning him, and then attempting to form a legitimate career as a puppeteer. However, the show he did was a sort of (extremely amateurish) parody of the Flash, who had a really oversensitive reaction to how popular it was and so decided to get intense in his war on crime, making him popular enough that the inhabitants of Central City (who are apparently all simpletons) stopped coming to the puppet show, so Abra Kadabra turned the Flash into a puppet and used him in the show.
- It's been revealed that Barry Allen brainwashed one of his Rogues, the Top, into becoming a genuine hero. Unfortunately the brainwashing went wrong, and the Top performed a similar, subtler Mind Rape on a number of the Flash's other Rogues before he went insane. This was used to justify how Wally West was able to befriend people who'd been written as hardened criminals (well, by Silver Age standards) while Barry was alive. Eventually the Top invoked this trope himself by undoing the brainwashing.
- The Sandman, no, not that one, reformed somewhere in the '80s after going through Body Horror, and became a reserve Avenger and joined Silver Sable's Wildpack for a while. Then John Byrne got his mitts on him again, and had the Wizard hypnotize him into his "proper" personality, then he nearly turned good in an early 2000 Peter Parker: Spider-Man comic in which he split into four different Sandmen (and one Sandwoman), but at the end of the story, his evil side takes over his good side, and his good side, outside of the main body collaboration, dies.
- The Bronze Age Superman story "Luthor Unleashed" has Lex suffer one painful defeat too many at Superman's hands, and decides to throw in the towel. He retires to the alien planet where he had once taken a wife (whom he had, till then, shamefully neglected) and tries to settle down to be a model citizen there. He even has a child. But despite his best efforts, he can't stop obsessing over the fact that Superman beat him. He finally builds a suit of Powered Armor in anticipation of Superman tracking him down, but then uses it to relieve his tensions by using it to wreak havoc on his new home, becoming its first supervillain. Superman does indeed arrive, and in the ensuing fight, Lex accidentally detonates a powerful gizmo and blows up the planet, killing his wife and infant son. He blames Superman and ends up more obsessed with his destruction than ever before.
- This is a pretty defining point about Lex Luthor and one of the best and most tragic examples. In many stories, Lex is a man who genuinely wants to do right by humanity and use his intellect for good. Its just that he can never get past his hatred of Superman. It also leads into the selfish spect of his personality: He wants to destroy Superman so the world will see him as the true savior of mankind.
- Eddie Brock, the former Venom, even after being separated from the symbiote. While trying to be a hero as Anti-Venom, he discovered that his benefactor, Mr. Li, was the supervillain Mr. Negative. He was so disillusioned that he now struggles with homicidal urges. Bets are open as to how long it will take for him to become Venom proper again. Plus all the times he went back and forth between being a villain and an Anti-Hero as the regular Venom.
- Brock lost his powers as Anti-Venom and tried to go Anti-Hero again... by murdering other symbiotes, who he views as inherently evil. Small wonder that he's back to being Ax-Crazy now that he's bonded to Carnage's spawn, Toxin.
- Spider-Man villain Norman Osborn has not reformed, but to the general public, it appears he has. However, nobody who actually knows him expects it to last, since everyone thinks he is going to have a Villainous Breakdown and go into a more overt form of this trope.
- Loki never stops trying to usurp Asgard and defeat Thor for many reasons. He is The Unfavorite of Asgard, being a trickster magician instead of a warrior, and so he can never truly believe that Odin and Thor truly love him as family, despite the fact that every time Loki's schemes fail, Odin and Thor always eventually forgive him and give him another chance. It got so bad that Loki actually let himself die at the conclusion of "Siege" and be reborn as a relatively innocent child in an attempt to escape Chronic Villainy. As the last remnants of his past life explains to the new Loki, he had become predictable in his treachery and, as a god of chaos and trickery, he would rather die than be predictable. And, predictably, all of that actually was a scheme to dupe others into thinking that Loki has truly changed (at the moment when everyone but Thor gave up any hope of redeeming him), by using Kid Loki's innocence and then overwriting his personality with the Old Loki memories. Proving once again that Loki cannot escape this trope. His younger self calls him out on it, though he tries to deny it.
- Greg Rucka's run on Elektra ended this way. After a whole run of issues in which she was forced to recognise just how much damage she'd done to innocent people, started seriously trying to reform, and came close to rejecting the conflict between the Chaste and the Hand altogether to just do good for its own sake, the Hand killed her new mentor and kidnapped the guy who first started her on the reform path. She killed all the Hand guys, but finally also killed the kidnapped guy because... well, presumably out of a momentary flash of despair that she'd been forced to kill a whole load of people, although it wasn't convincingly explained. There were stories that this was due to Executive Meddling, because the writer of an imminent crossover event decided that he wanted "classic" Elektra to be involved in it.
- Any Lucky Luke story about trying to redeem the Dalton Brothers is doomed to end with them being back to villainy, due to them being Card Carrying Villains to such a degree they genuinely think leading a honest life is horrifying. Most notably, Marcel Dalton, which involves their uncle trying to reform them as employees in a bank he recently bought, has the entire book focused on them struggling to get accepted in the town and competing with a corrupt rival banker. They eventually succeed... only for the Dalton to turn on their uncle at the last minute and escape so they can go back to being criminals. After this event, Marcel Dalton recognizes his nephews cannot be redeemed, and allows Luke to arrest them.
- Button Man: After years of trying to get away from the Killing Game and living in peace, Harry finds himself drawn back when he runs out of funds, plus the simple fact that he enjoys these duels to the death and is damn good at it.
- Sabretooth is a big example, when it comes to his predatory instincts. He was inverted during AXIS and tried to genuinely atone for all his evil. But, the inversion wasn't meant to last. He shows signs of slipping in Uncanny X-Men (2015) when he's hunting a dinosaur and tries to reign himself in, but can't. Chapter 17 has a lengthy inner monologue with him admitting that his inverted self is a lie, but confessing that he doesn't wanna let it go. He tries to hold on to it, but the old him is coming & fighting back -the Creed who cared about nothing but the kill. He also thinks about how he daydreams of slaughtering the X-Men while he fought alongside them, because that's what he was supposed to be doing. Monet St. Croix becomes his Morality Chain when he thinks about fighting for her -wanting to help cure her curse and stay true to his promise of keeping her secret. The run's finale showed he ran off with her.
- Sadly for the reformed Creed, he's not doing as well with the Resurr Xion relaunch, He doesn't appear completely evil yet, but he's clearly not as good as before. He's no longer with Monet and was shown living by himself in the woods at the start of Weapon X. For now, he's focusing all his sadism & murderous tendencies on bad guys -as opposed to innocents. Word of God says he's going to continue exploring Creed's morality in the series.
- A downplayed case in Spirou and Fantasio; when Zantafio was first introduced in Spirou et les Héritiers as a crooked rival to Fantasio for their uncle's legacy, the book ended with him saving Spirou and Fantasio, reconciling with them and giving up on the legacy (despite Fantasio being willing to share it), deciding instead to make his own life in Palombia. When he came back in Le Dictateur et le Champignon, it turned out he had become a ruthless dictator in Palombia and was now planning to make a War for Fun and Profit, putting him in an antagonistic role once again. Every appearance after this has despicted him as possibly the vilest character in the series.
- Cruella de Vil in 102 Dalmatians. Went to jail, got reformed, but an accident with the main puppy caused her to start seeing dalmatian spots all over town. Kind of a disturbing scene. In a perversion of Pavlov's Dog, the researchers responsible for Cruella's behavioral modification into the saintly Ella accidentally discovered that the sound of a bell reverses the process. Needless to say, the minute Ella hears a bell ringing, she's back to being the sociopathic Cruella. This in a city that is famous for a hugantic friggin bell by the nickname of Big Ben.
- Lord of War has Yuri Orlov, the greatest arms dealer in the world (described to have been on first-name basis with several dictators), tries to reform and run a lumber company when a Federal agent tells his wife what he does. But trying to live honestly is too hard (or not so much hard as boring), so he goes back to gun-running.
- Gollum in The Lord of the Rings is a pretty solid example. After being subdued, taken captive, and his life subsequently spared by Frodo, he is slowly calmed and rehabilitated by Frodo's attempts at kindness until he ultimately breaks down in a "fight" between his two personalities, and defeats his Gollum side, reverting to a much more cheerful and helpful Sméagol persona. Then, an unfortunate run-in with Faramir has him beaten and seemingly betrayed by Frodo, making him break once and for all back into his murderous, deceptive self. A similar process occurs in the books, but is much more subtle.
- Michael Corleone in The Godfather Saga: "Just when I thought I was out, they pull me back in."
- His father, Vito, wanted to avert this chronic loop and was truly brokenhearted when he failed.
- Well done by Mickey Rourke in the titular character of Johnny Handsome.
- Frank Abagnale Jr in Catch Me If You Can eventually becomes addicted to the thrill of living like a playboy by conning money and eluding the authorities, while becoming tired from having to look over his shoulder all the time. He needs his father's support to stop, but Frank Sr. refuses for selfish reasons. Even when Frank tries to settle down his past catches up with him and he goes further into the criminal lifestyle. When Hanratty finally tracks him down in France, Frank almost seems like a thrill-seeking junkie, and Hanratty has to save him from getting himself killed. Subverted when he is released from prison to work for the FBI catching criminals like himself, and he almost goes back to his former life. He comes back into work on Monday and greets Carl as usual.
- Shot Caller: Jacob continues the Aryan Brotherhood's activities as soon as he's out of prison, as the only acceptable retirement is death. Ultimately, he gives up his freedom and usurps control over the entire organization as the sole method to reliably protect his family from reprisals.
- In Soon I Will Be Invincible, Dr. Impossible knows that no matter how perfectly he builds his machines, no matter how well he prepares his world domination plot, no matter what he does, the invincible superhero Corefire will just waltz through all his weapons and defenses, beat him up, and put him back in jail. Probably on live television. But as of the book's start, he's on his thirteenth attempt.
- He also mentions that people at the extreme far end of the intelligence bell curve - like him - suffer from "Malign Hypercognition Disorder", which compels them to be evil supervillains and try to Take Over the World. Even though he knows he'd be better off using his genius in more legal ways, he can't help trying to conquer the world.
- The Lord of the Rings: Smeagol really strived between his two selves about his conflicting desires and his relationship to Frodo. It is made clear, that Sméagol (as he was originally completely sane) killed his friend in order to take hold of the Ring (Gollum references Sméagol being a murderer in both films he/they are featured in.) The Gollum personality came later, during his decades of isolation. Really, he's an example of a person who instantly fell into the power of the Ring, but was otherwise a relatively decent sort of person. A person very susceptible to temptation. Smeagol ends up representing in his mind who he used to be and what he lost, while Gollum was what he became and the safety that he had in staying the same, rather than remembering or regretting.
- Harmony Kendall from Angel. During her appearances on the show, her Chronic Villainy seemed to alternate between tragedy and Ass Pull. Either way, it seemed like she genuinely wanted to do the right thing, even though it was against her vampiric nature. She even once said, "It's not like I have a soul! I have to try a lot harder!"
- Spike from the Buffyverse flickers like a moral strobe light. Dark: the punk vampire based on Sid Vicious, his original form. Light: helps Buffy Save the World from Angelus because he likes it here and because he loves Drusilla. Dark: has Angel tortured for a phlebotinum ring. Light: has a chip in his brain that stops him hurting people, but helps Buffy because he can still attack other demons. Dark: drives a wedge between Buffy and her friends (The Yoko Factor) and kidnaps a doctor to get the chip removed. Light: falls in love with Buffy and goes back to fighting on her side; cries when she dies. Dark: takes sexual advantage of the risen Buffy's depression; tries to rape her when she comes to her senses. Light: gets his soul back, fights on Buffy's side again. Dark: used as a sleeper agent by The First. Light: saves the world at the cost of his own life. Dark: becomes a ghost and tries to rob Angel of his prophesied redemption. Light: takes over Angel's former job of helping the helpless; ends up fighting with Angel in the last battle. I count 11 toggles of the good/evil switch.
- Arvin Sloane from Alias appears to go straight a few times (though whether the attempts were genuine is debatable) but he inevitably has to get involved with the prophecies of Rambaldi that he has an obsession with. One particularly disturbing scene has a Mook who states that Rambaldi's ultimate plan was to become immortal, causing Sloane to snap at his shallowness and beat him to death. (While that season showed that Rambaldi's plan was far more than immortality, the next season showed that a key part of it was immortality, which Sloane pursued with disturbing gusto.)
- The tragedy of Londo Molari in Babylon 5. He is a good man at heart and frequently tries to use his influence for good or turn his back on the constant schemes of his old allies. But he is addicted to power and it takes only slight nudges from his former friends or personal tragedies to have him forget about his ideals and the previous times he set lose an avalanche of events he couldn't stop.
- Breaking Bad: Former chemistry teacher and ruthless meth kingpin Walter White always goes back to his meth business, regardless to how much danger he puts himself and his family in. In the last season, he eventually decides to leave the drug business and try and regain some semblance of normalcy in his life. Naturally, his crimes are discovered by his brother-in-law in the DEA less than 24 hours later, forcing him to go back to being Heisenberg again.
- Sylar (a.k.a Gabriel Gray) from Heroes has become quite familiar with this trope lately. The show tried to play around with the idea of redemption somewhat inconsistently during Volume 3, but it didn't take, partially thanks to liberal amounts of extreme rejected reform, and as of the current story arc, he's back to his superpowered, sociopathic ways, only now, with 90% more snark and a Kid Sidekick.
Parkman: The last time I was in your head, you turned my life into a living hell. What makes you think I'm gonna risk that?Sylar: Janice and the kid. I really do want to change. But I'm insane, remember? All I have to do is point.
- After seeing his biological father in a recent Volume 4 episode, however, this tendency might be In the Blood. When Sylar displays his regenerative ability, Daddy Gray, who is dying of lung cancer, tries to take it, even though he previously claimed to have gotten bored of killing and swore off it many years ago.
- His actions have finally caught up with him by the end of the final season. His slew of trauma, murder, and issues all come to a head, and, as a last resort, he hunts down Parkman to have his mind wiped clean. Parkman isn't buying it and refuses until Sylar threatens his family.
- The killer in the Criminal Minds episode "The Big Wheel" kills not because he wants to, but because he has a compulsive disorder forcing him to. The most he can do to stop himself is add the message "help me" to a video of one of his killings before sending it to the police. It seems that, in the past, he'd been a genuinely heartless killer, but the son of one of his victims somehow sparked in him the last vestige of goodness and made him reform. Unfortunately, when the kid is about to move away, the stress of this causes murder compulsions to overwhelm him. Towards the end of the episode, he dies, but not before telling the kid "forgive me...". Poor guy.
- There was the guy from Everybody Hates Chris, who he sent to jail. He comes back and asks Chris to help him complete high school. They succeed, but he goes back to robbing because it's more exciting than a real job.
- Happens both times the Stargate Atlantis team tries to use the retrovirus on Michael. The second time, they used it on a whole hive ship in addition to Michael. They just never learn.
- In later seasons, Deep Space Nine's recurring bad guy, Gul Dukat, was portrayed as being on a path of redemption or at least Noble Demon status, as he saved his mixed race daughter from slavery (despite cultural precepts which said he should have killed her) and fought against the newly antagonistic Klingons as they invaded his people (seemingly gaining an ounce of empathy after being the underdog for once). Unfortunately, he finds an opportunity to regain power on Cardassia, and reverts right back his tyrannical old self. When his plan is revealed and he betrays the good guys, he even lampshades how it never seemed quite right that they were on the same side. Later, after he has been defeated again and his daughter has been murdered in front of him, he has a Heel Realization and embraces it, going full Card-Carrying Villain for the last part of the series.
- General Hospital: Manny Ruiz, an Ax-Crazy serial killer who terrorized Jason and Sam for months, is revealed to be suffering from a brain tumor that apparently caused his psychotic tendencies. When Patrick Drake removes said tumor, he's believed cured... but he soon returns to his villainous ways.
- Played for drama in The Sopranos with Cousin Tony.
- Glee is a perfect example in the Ass Pull category of this trope. No matter how many times Sue Sylvester takes a liking to the club or helps them or shows some depth to her personality, it will be completely forgotten by her next appearance and she will always return to her scheming and villainy.
- in Once Upon a Time Gold's arc is built over playing with this trope. He becomes too reliant on the power dark magic has to offer him, and eventually misses out on all the uppotunities he had to become a good man and a hero, no matter what he had to sacrifice in order to get this uppotunity (his wife, his child - twice, his second marriage...)
- Regina eventually subverts this trope, after spending most of seasons 1-2 being chronically evil.
- Christianity (particularly Orthodox) states that this is the main cause of people's suffering. As a consequence of the Fall of Man, people cannot help but sin, unless they recognize this fault, repent, and overcome it with God's help.
- Macbeth realizes several times, most prominently after the feast, the wrongness of what he's done and that he still has a chance to turn back. He doesn't.
- Similarly, Doctor Faustus almost repents frequently throughout the play, but keeps convincing himself that he's too far gone, even when an angel tells him otherwise. Even as he's about to be sent to Hell for eternity, Faustus makes a speech begging to be given more time to live so he can repent, even though he could easily just repent then and there and save himself.
- Fate/stay night's Kirei Kotomine, so, so very much. He perfectly understands right and wrong, just the 'switch' inside humans where we feel good for doing good is stuck the other way. Did some evil, felt happy, realised he was doing evil, tried to do good, became a priest specialising in healing magic, and settled down with a family. His wife died, and he realised that all he felt was disappointment that he hadn't been able to kill her. He then realises that he is utterly unable to get any pleasure from life unless he's causing pain and suffering. From there, it just took a small push (thank you, Gilgamesh) for him to try to unleash every evil known to mankind on the world. When The Hero asks him why he's doing it, he replies with a speech that can be summed up as: "Just as some people find music or art entertaining, I can only find amusement in watching other people suffer."
- Michael in Grand Theft Auto V. A former bank robber who retired and went into Witness Protection, he finds himself bored by civilian life and cannot come to terms with it, and therefore embellishes the financial troubles that his wife Amanda's spending causes him in order to more easily justify and excuse his wish to return to a life of crime.
- As mentioned under Science-Related Memetic Disorder, this is a recurring problem for reforming mad scientists in A Miracle of Science; the medication makes their heads fuzzy so they can't think clearly, and they tend to abandon it and relapse. In the words of one, "When you're a recovering mad scientist, you're always afraid you'll lose control and wake up some morning with a half-built time machine and a plan to go back in time and pants Hitler..."
- Oasis suffers from this in Sluggy Freelance. Even when she resists her insane obsession with Torg and fights crime, she's still a particularly brutal Vigilante Woman who's a little too callous about slaughtering dozens of people. Her assassin instincts even kick in during mundane tasks, such as when she makes pancakes and "doesn't stir the batter so much as stab it lots."
- Defection: Keanan's mother, one of the higher ups on the list of big bads, tells him that she isn't a villain because she wants to be, but because she is insane.
- To be fair to the woman, The Nostalgia Chick has tried to be a good person before, and she does still have Pet the Dog moments. She's just so miserable in life and willing to crawl back into a bottle because she's lonely that it just never really lasts.
- Ask That Guy with the Glasses: Invoked by the title character.
- Happy Tree Friends: Flippy manages to get rid of his Superpowered Evil Side in "Autopsy Turvy", but "On My Mind" showed that Evil Flippy's destruction was undone by Snap Back just like all the other deaths on the show.
- Lampshaded in Justice League, where the Trickster returns to his obsessions and is talked down from it by The Flash.
The Flash: (admonishingly) James... You're off your meds, aren't you?
The Trickster: Better off without 'em. Take 'em if I start feeling down.
The Flash: You know that's not how the medicine works. You're not well!
The Trickster: I'm fine! (brightening up) You wanna throw some darts?
The Flash: No. (beat) Listen, James, you're wearing the suit again!
The Trickster: I am? (looking at his suit) Well, what do you know...
- In Avatar: The Last Airbender, we have Jet, a character with justified obsessions with taking down the Fire Nation, and incredibly unjustified actions towards that aim. Eventually, he decides to stop and try to live a normal life as a refugee. However, upon discovering that Zuko and Iroh are Fire Nation (they were technically lying about being escaped Earth Kingdom POW's, but were still harmless nonetheless), his attempts to convince others of this fall on deaf ears, and his obsessions get the better of him, eventually resulting in him openly attacking them in a crowded shop, getting arrested, Brainwashed, sent to kill the Avatar, and eventually Killed Off for Real. Ouch.
- In Conan the Adventurer, Wrath-Amon's Dragon, Windfang, discovered a spell that would restore him to his human form. Soon after, he returned to his homeland, accompanied by Conan and his companions, to reclaim the throne. Unfortunately, two hundred years had passed since he became Windfang, and the entire kingdom, including the woman he loved, was long since gone. After Wrath-Amon found him and demanded that he return with him, the poor guy surrendered without a fight, now knowing that he had nothing to go back to.
- In the WordGirl episode "Tobey Goes Good", Tobey McCallister III finally realizes that, to win WordGirl's affections, he must convert to the side of truth and justice. However, this is completely wiped away once his completely superior, humongous robot loses "The Young Inventors Challenge and Friendly Competition" to a combined apple and egg slicer because the judge liked the free food.
Tobey: I have to hand it to you, Word Girl, you were right about me. I hadn't changed into a no-good do-gooder! *Quickly wipes a tear away* It doesn't pay to be nice! After all, try to be nice — not destroy things — and look at what happens! You end up losing to an egg-slicer!
- Xiaolin Showdown had an episode with the villain Jack Spicer offering to study with the heroes at the temple and become a xiaolin monk himself. His greed and ambition eventually get the better of him when he's presented with an opportunity to steal their Shen Gong Wu. The rules of a subsequent Xiaolin Showdown force him to talk to Omi about his betrayal and admit that he really was trying to reform.
- In an even straighter example of the trope, the only reason he ran away was because he was afraid that he was not good at being good, and Failure Was The Only Option. Maybe Spicer's a bit smarter than we'd guess.
- A Spongebob Squarepants episode had him befriending Plankton. Everything seemed fine until Plankton steals a krabby patty.
- The Movie of Codename: Kids Next Door portrayed this trope tragically with the Delightful Children. The brainwashing Father put them under is so incredibly powerful and rooted deep into them that any attempts to undo it would be temporary at best, and they'll morph back into their evil selves. They cannot be good because they are forever under Father's influence.
- Remy Buxaplenty on The Fairly Oddparents makes a truce with Timmy at the end of one episode. In his next appearance, he uses Timmy's new-found trust to trick him into his latest scheme.
- Yuck, Yin and Yang's Evil Twin from Yin Yang Yo!, ends up succumbing to this due to a particularly vicious case of Reformed, but Rejected from the two, culminating in beating him senseless at his unveiling of a statue dedicated to their new friendship, destroying the statue in the process.
- In one T.U.F.F. Puppy episode, Snaptrap falls in love with Dudley's mom and quits D.O.O.M. and joins T.U.F.F. for her. However, he has trouble with the whole "good guys don't steal" thing, and he keeps letting all the bad guys get away.
- Dr. Doofenshmirtz of Phineas and Ferb has twice attempted to quit villainy. The first attempt involved becoming a cheese maker, but that went south when Perry the Platypus, in a moment of weakness, ate the world's tastiest cheese Doof prepared while the doc's back was turned. This led Doof to use his cheese-aging 'inator for evil in response. The second attempt was in 'Agent Doof'; There, Doof joined the OWCA, but became a Hero with an F in Good, and subsequently fired. This time, however, he's elated to hear Major Monogram state that Doof was more of a threat inside the organization than outside it and went back to villainy thinking he still had it. He turns good for real in the Series Finale.
- This was intended to happen to Kevin in Ben 10: Alien Force: the writers originally intended to have him starting to use his energy absorption powers in season 3, which would have caused him to gradually turn evil again, and, despite trying to resist the urge, eventually turn back into Kevin 11. This plot was however rejected by Cartoon Network in favour of bringing back Vilgax. Eventually, the idea was accepted for season 1 of Ben 10: Ultimate Alien, but with several changes, including Kevin reforming again at the end.
- In Ultimate Alien, the Vreedle Brothers were last seen having reformed from their life of crime and became Plumbers, even ending up opposing their mother when she tried taking them back in crime. Comes Ben 10: Omniverse, we learn they ended up blowing up the Plumber Academy for fun, left and became thugs again.
- A particularly sadistic exemple in The Batman, where Dr Hugo Strange eventually succeeds in curing the Ventriloquist from his insanity. The guy immediately tries to go back to a normal life... but Strange, being who he is, immediately works to ruin his life and turn him insane again for the sole sake of seeing how it'll turn out. By the end of the episode, he is back to being a criminal.
- Norman Osborn in Ultimate Spider-Man is cured from his mutation into the Goblin at the end of Venom's Bomb. As he is trying to get back to a normal life, he genuinely attempts to make up for his crimes, tries to be a better father to Harry, and even becomes a super-hero as Iron Patriot. Sadly, a few episodes later, Dr Octopus, still trying to get revenge on him, kidnaps him and turns him back into the Goblin.
- In Star vs. the Forces of Evil episode "Princess Quasar Caterpillar and the Magic Bell", Ludo is trying to give up his evil ways, particularly the part where he tries to steal a magical artifact from a princess. It becomes an uphill battle when his well-meaning brother Dennis begins rebuilding his castle from Season 1 and hires some of Ludo's old minions to help.
- Thomas the Tank Engine: After the Spiteful Brake Van torments Douglas by deliberately making his trains late, Donald confronts him on this. The Spiteful Brake Van promises to stop his ways, but he tries to do his same shtick again when Douglas is trying to assist James on his hill. Needless to say, the Spiteful Brake Van ends up getting crushed by Douglas for his troubles.