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  • Amphibia: Despite King Andrias being an evil, power-crazed tyrant, his defeat at Anne's hands is downright brutal, dark, and sad. She strikes him at the exact moment he decides to repent and open himself up to defeat. Whilst Andrias does survive Anne's finishing blow and later cement his repentance, Word of God confirms that the damage has numbered his days.
  • Arcane: Silco is a ruthless sonofabitch who's responsible for destroying the sisters Vi and Powder's adoptive family and flooding the streets of the Undercity with Shimmer. His relationship with Powder turned Jinx, though surprisingly sweet at times, is also deeply unhealthy as he encourages her worst traits while jealously trying to keep Vi away from Jinx by lying that Vi's only there for the Hextech crystal. Yet he dies rather sympathetically. In an intense standoff with Vi over Jinx, Silco prepares to shoot Vi but in a moment of absolute panic, Jinx mortally wounds Silco. He spends his dying breath providing reassurance of his love to the daughter who just riddled him with bullets as the girl profusely mourns his death.
    Silco: I never would have given you to them. Not for anything. Don't cry. You're perfect.
  • Archer:
    • Major Jakov. The sheer brutality with which Barry usurps and then murders him makes his death a dramatic moment, both for the audience and In-Universe.
    • If he even counted as a villain, then Captain Murphy-he wasn't even a bad guy, just a harmless, if unstable, guy who went nuts and started making terrorist threats due to being trapped at the bottom of the ocean, but Archer's idiocy gets him killed, and he tells them how to escape the lab with his dying breath.
  • In Avatar: The Last Airbender Princess Azula is brutal and manipulative – and is only fourteen, with a long history of parental abuse, grooming, and learned violence-for-violence type behavior. Usually she's such a chessmaster that you forget to feel sorry for her, and then she spends the whole series finale going steadily crazier and crazier, with her Freudian Excuse coming to the surface as she starts hallucinating her mother being near and becomes paralyzingly desperate for her father's validation. She finally snaps after she loses to Katara, and the last shot of her in the series is her screaming and sobbing uncontrollably, with Zuko and Katara themselves looking upset that nobody ever tried to help her. Azula in the end knows that no one is coming to help her, and nobody wants to, so it breaks her. Azula got the help she needed eventually by interacting with Zuko and her mother, and even when she somewhat reverted to her old ways, she still has Zuko saying he still wants to be her brother.
    • Implied also for her great-grandfather Fire Lord Sozin. He began the Hundred Years War and left his former best friend Avatar Roku to die in an erupting volcano so they couldn't stop his plans. By the end of his life he was a sad old man, realising how bad his ambitions were, but it was too late to stop it.
    • Jet. The young guy is introduced kicking an elder citizen, trying to burn down an innocent Fire Nation colony and trying to kill Sokka to silence him, but in Book Two, Jet is revealed to have severe issues after his own village was burnt down by ruthless Fire Nation soldiers, losing his parents in it. And when Jet tries to turn over a new leaf and helps Team Avatar find Appa, he is killed by Long Feng, one of the people in the Earth Kingdom he fought so hard to save in the first place.
  • Batman Beyond: Ian Peek, the Villain of the Week in "Sneak Peek", is an unethical and slimy Paparazzi who murdered a scientist to steal an intangibility belt and use it to jump-start his career, and nearly exposes Terry's secret identity for the sake of ratings. However, his ultimate fate is played surprisingly sombrely; his belt malfunctions and leaves him permanently intangible, resulting in him sinking into the center of the Earth, presumably for all eternity. Terry is noticeably saddened by this, regardless of how much a scumbag Peek was.
  • In Beast Wars, although it's fairly minor, Dinobot does seem to briefly mourn the untimely deaths of the Predacons in victory. Whether he still feels a sense of affection and camaraderie for his former teammates (as Optimus assumes) is left unclear, though knowing Dinobot it's more likely he saw it as a waste of warriors who deserved honorable deaths. He even quotes William Shakespeare!
    Alas, poor Tarantulus! I knew him, Cheetor! This is the leg that stalked so many victims! (Sighs) So it should come to this...
  • In Beast Machines, Rhinox, a former ally, has become Tankor, a powerful enemy. After Tankor's death, the heroes hold a memorial for their fallen friend.
    Cheetor: He wasn't just one of us... He was the best of us.
  • Beetlejuice: Claire Brewster can be considered villainous, with her massive ego and strive to humiliate Lydia (she'd succeed if not for the Ghost With The Most). But one episode had her rung through the wringer on a Beetlejuice-staged foreign exchange student program to where she's dirty, disheveled and her clothes are torn. When she tries to enter her own home for a big fancy party, the butler dismisses her as a poverty-stricken waif. Lydia (at the party) sees Claire outside crying her eyes out, so she sneaks Claire in through a back window, cleans her up and gets her ready for the party.
  • Vlad Masters of Danny Phantom fame pulls more than a few evil acts. Still, in his final moments he not only had to deal with the fact that everyone he wanted would not give him their love, but his most hated "friend" of all people rejected him when he refused to change his evil ways. Now, Vlad doesn't have anyone and is stuck in an area where he has to confront his greatest fear: loneliness.
  • Darkwing Duck: In "Star-Crossed Circuits", D-2000 has spent the entire episode causing trouble, first acting as a Job-Stealing Robot and then becoming a yandere obsessed with Darkwing. However, Launchpad still gets sniffly when it shuts down proclaiming its love for Darkwing, despite understanding how much it needed to happen.
  • This happens a lot in the DC Animated Universe.
  • Exo Squad:
    • General Shiva was a Neosapien commander imprisoned for not slaughtering the human Australian Resistance to the last man, he is given a chance to "redeem himself" by retaking Venus, which he knows to be a Suicide Mission. But, being a good soldier, he gives it a go anyways. When he is mortally wounded after being shot down, even the initially hostile Exoscouts who find him see it as a tragedy.
    • While about as complete a monster as there can be, Phaeton still has a brief moment in the final hours of the war when he recalls perhaps the only time in his entire life when he felt at peace and content. It reminds us that once upon a time Phaeton might have been more than a half-mad genocidal dictator, and between being born into a Slave Race and fighting multiple wars, exactly how little room there was for anything decent in his life.
      Phaeton: Have you ever known happiness, J.T. Marsh?
      Marsh: Not since I met you.
      Phaeton: I was happy... once. It was after the First Neosapien Rebellion. I had been invited to speak at the University of Chicago on the future of Neosapiens. Before the speech I decided to take a walk. It was a beautiful day, and the sun was warm, and I heard church bells in the distance... and for a brief moment, I was at peace.
  • Played for laughs in the Futurama episode "Anthology of Interest I". In a fantasy sequence, Bender is depicted as a giant who smashes up a city before being killed. As he lays dying, he laments he was unable to carry out his dream of killing all humans and expires on this line:
    Bender: "Who's the real seven billion ton robot monster here? Not I. Not... I."
  • Gargoyles has the Captain of the Wyvern Castle guard, who was so wracked with guilt for accidentally causing most of the Gargoyles' deaths when he betrayed Wyvern Castle to the Vikings that he spent the next thousand years haunting the castle's remains after his death.note  Hakon was also haunting the site, but out of continued hate for Goliath (who ironically had nothing to do with either of their deaths who killed each other Disney style, although he wanted to deliver a gruesome kill). When Goliath shows up at the castle again, they harass him, make him hallucinate and attack his own friends, and, finally, drive him to an ancient ritual site where they can exchange his life for theirs. The Captain realizes what evil he is about to commit, repents, and uses his brief physical form to destroy the site. With his last moments, he thanks Goliath for forcing him to acknowledge his sins and begs for forgiveness as he travels to the afterlife. Goliath happily mourns him as a friend who is finally at peace. Hakon is still stuck, trapped within the ruined site, alone to wallow in his hate.
  • Infinity Train: Simon Laurent in Book 3 ends up as one of these. Yes, he's a multiple murderer and tried to kill his friend Grace a grand total of 3 times, but he was also taken away from his family as a little kid, betrayed by his Parental Substitute in the train, and taken in by Grace who taught him the Apex's deeply flawed philosophy, which ultimately resulted in him losing everything he ever cared about and dying a Family-Unfriendly Death at the age of 18 when a Ghom drains him. Even Grace is saddened by his death due to how horrific it was and how easily he could have turned out better.
  • In The Legend of Korra, Tarrlok and Amon/Noatak end up on a boat escaping Republic City after Noatak's lies are revealed to the public. Deciding they could not live, for any various amounts of implied, but unsaid reasons (being the legacy of an evil bloodbending criminal, knowing they'll be hunted for the rest of their lives, coming to terms with evil deeds), Tarrlok uses an Equalist shock glove to blow up the boat's engine, killing both of them. This follows Noatak having said he wanted to start a new life with his brother. Tarrlok even remarks "it will be just like the good old days," and Noatak remarks how he almost forgot the sound of his own name and sheds shed a single tear right before the explosion. Depending on who you ask, the tear indicates (among other interpretations) that he knew what Tarrlok was about to do and didn't try to stop him, or that he genuinely wanted to have the peaceful life with his brother that he'd been talking about.
  • Miraculous Ladybug: Chloé Bourgeois gets a minor one at the end of "Revolution" when her parting shot at Marinette backfires. Her pride and arrogance completely shatter in that moment and she drops her mask of entitled brattiness as she breaks down tears, showing the audience what's truly underneath it: a lonely and broken teen who has realized her actions have left her friendless, powerless, and under the control of a more tyrannical mother.
  • Monster Loving Maniacs: Edith, Ernest, and Bo can't help but feel hollow and unsatisfied by defeating Dracula, understanding that by killing him and being made true monster hunters as a result, they had essentially proven Arthur's point about it being impossible to help all monsters (on top of also learning Dracula's interest in the Van Alten family was driven by his loneliness and how dead he felt inside without a family of his own). This drives them to resurrect Dracula shortly afterwards, this time intent on helping the one monster they failed to save.
  • Primal (2019): That poor Argentinosaurus in "Plague of Madness" never wanted to be bitten by an infected Parasaurolophus and subsequently transformed into a flesh-hungry undead monster. Its demise by falling into lava is horrific, and at the same time, downright merciful. Even Spear and Fang, who the infected Argentinosaurus had spent the entire episode trying to kill, both watch the sauropod burn to ashes mournfully.
  • Samurai Jack:
    • It's very hard not to feel sorry for the Villain Protagonist of "The Tale of X9", a robotic assassin, who was one of several murderous robots created by Aku, but was the only one given emotions and feelings. After years in the service of Aku all the other robots of his series have been destroyed, but he has survived because of his emotions. However, when he meets a tiny dog named Lulu (sweet thing), he finally hangs up his assassin hat for good. Unfortunately, when Jack arrives, Aku becomes desperate and decides that he has to pull his greatest assassin out of retirement by holding Lulu hostage. Jack knows nothing of this, and when X9 launches his attack, Jack cuts him down just as effortlessly as he would any other mook. His final words are asking Jack to finish caring for his now abandoned charge.
    • Princess Mira from "The Princess and the Bounty Hunters" is another enemy of Jack's that is after him for a noble cause; she hopes to use him as a bargaining chip to free her nation from Aku's tyranny. When she and her allies ambush Jack, he effortlessly dispatches all of them with only Mira standing. Realizing that she is so badly outclassed by the samurai, Mira can only slump over and cry, seemingly accepting that she will never save her people, while Jack wanders off into the forest without a word.
    • In Season 5, Jack is pursued by female assassins known as the Daughters of Aku, who were brutally trained from birth by their abusive mother with the purpose of killing the samurai. While Jack himself is initially unaware of this, it's made abundantly clear to the viewer that they were just abused young women than anything else. When he is forced to kill one in self-defense, its treated as a very somber moment for marking the first time he killed a real human being and not a robot. After killing five more in combat, Jack is so wracked with guilt he begins to hallucinate with dozens of crows calling him "MURDERER".
  • Played for Laughs in the She-Ra and the Princesses of Power episode "Roll with It" when a tiny spybot is accidentally destroyed.
  • It's almost impossible not to feel bad for Gargamel and Azrael in most of the cases he's defeated in The Smurfs (1981).
  • South Park: A non-lethal version. In South Park: Post Covid: The Return of Covid, Eric Cartman self-destructive behavior leads him to become a homeless alcoholic whom nobody wants to be around. This would be pitiful enough if it weren't for the fact that he ended up like this because his original future self went back in time and willingly sacrificed his happy ending so that Stan, Kyle, and Kenny could have a second chance at earning theirs, which prevented him from leaving South Park, meeting Yentl, and having a Heel–Faith Turn; instead leading him down a path of complete misery and loneliness. Stan and even Kyle feel extreme pity for him.
    Stan: Man, poor Cartman [Cartman is across the street throwing drunken fits].
    Kyle: It's so sad he never did anything with his life.
  • The death of Spider-Carnage in Spider-Man: The Animated Series. He was a demented, Ax-Crazy loon who was trying to set of an Omniversal Metaphysical Annihilationapocalypse, but when he has a Heel Realisation and kills himself it's all but impossible not to feel bad. There's just something about seeing someone with the face of the show's hero brought so low that not only does suicide seem like a good idea, it's the best option that there is.
  • Savage Opress from Star Wars: The Clone Wars caused more than his share of death and destruction while apprenticed to Count Dooku, Asajj Ventress, and later Darth Maul. However, this was due in large part to his brainwashing at the hands of the Nightsisters, and when he is unceremoniously impaled on the lightsabers of Darth Sidious, he dies in his brother Maul's arms, expressing regret that he had not reached Maul's expectations.
    • Queen Scintel surprisingly. Her arc presents a horrifyingly accurate look at slavery and she herself is the unrepentant head of a slaving empire. Despite this she grows genuine affection for Anakin and while he doesn't reciprocate romantically, he still grows a certain attachment to her. However all her plans for to make Zygeria a galactic power come crashing down on her when Count Dooku demonstrates just how much above her the Sith really are and strangles her with the Force. She dies realizing she was as much a slave as anyone else and willingly tells Anakin where his friends are being kept.
    • In Star Wars Rebels, the death of Darth Maul is a major Tear Jerker, one of the biggest in the whole series, when he realizes how badly he's failed and how much of his life has been completely wasted. He's past his prime, everything he has worked for is for nothing, his family is dead, and he spends his time tracking down Obi-Wan Kenobi for one more duel. As Maul dies, the two have a quiet conversation on the Chosen One and Maul saying that he will avenge "us" - Maul, and either his brother or Obi-Wan.
    • Also from Rebels, there's Imperial Lieutenant Yogar Lyste. Despite being a jerkass who seized land from innocent farmers for the Empire, it's hard not to feel sorry for him when he gets framed for treason by the actual mole. He's last seen being dragged away protesting his innocence, and the only person who actually seems to care about what happens to him is the same man who framed him in the first place.
  • Steven Universe:
    • Before being corrupted, Jasper is revealed to be an angry and vengeful loyal soldier who, from her point of view, lost her colony, her planet and her leader (Pink Diamond) because of Rose Quartz. She spends her last moments roaring at Steven for every wrong she thinks Rose Quartz did. On top of this, it's implied she's nothing more than the equivalent of a grown up Child Soldier who's been indoctrinated from birth to think the way she does. Word of God later confirmed that she refused Steven's help because she hated herself for being (in her eyes) too weak.
    • Bismuth is also this. Fighting in the war against Homeworld, she saw her comrades shattered at the hands of Homeworld Gems. She believed they'd lose the war unless they stopped following Rose Quartz's policy of not shattering enemy Gems. When she made a weapon designed to do just that, Rose was mortified. She poofed Bismuth to keep her from telling the others, and lied to her friends about her disappearance for 5000 years. When Bismuth is stabbed with Rose's sword by Steven, she delivers some heart-wrenching words before she poofs.
      Bismuth: You should have shattered me back then. At least if I were in pieces, I wouldn't have to know how little I mattered to you! You didn't even tell 'em. You bubbled me away and didn't ever tell your friends. My friends!
      Steven: I'm going to tell them. I'm going to tell them everything.
      Bismuth: [chuckles] Then you really are better than her.
    • The Rubies are all generally incompetent, childlike morons, aside from Eyeball, who has a little more experience due to being a Shell-Shocked Veteran. All of them are Thrown Out the Airlock by Steven, a possible Fate Worse than Death, due to the fact Gems don't need to breathe and are The Needless, condemning them to a possible eternity of floating through space, something Steven expresses heavy guilt over in later episodes, in addition to the fates of Jasper and Bismuth.
    • Peridot, in her first appearances can be considered this. She was only sent to Earth to perform a checkup on the progress of the Cluster, something she had little to no involvement with the production of. As a result, she had her work constantly interfered with and all her equipment broken by the Crystal Gems solely because she was from Homeworld. Later on, when she had to be escorted by Jasper to get rid of the Gems so she could finish her work, she ended up being stranded on Earth with the Cluster about to emerge and destroy the planet. Even worse, the Crystal Gems have no knowledge of the Cluster and thus continue to hunt her down and stop her methods of getting home because they still view her as an enemy. Eventually, while she’s on the verge of a Villainous Breakdown over her situation, she gets caught by them and loses all her tech she had never been without before, having to then adjust to a completely new lifestyle she is essentially forced into. Her only option then is to work with her enemies to save herself and the planet she was stuck on. While she does end up pulling a Heel-Face Turn, saving the Earth, gaining new powers and ending up much happier than she was on Homeworld by the end of the series, one can’t help but feel bad about all she had to go through simply because she was trying to do her job.
      Peridot: "Go to Earth", they said. "It'll be easy", they said.
  • In the Teenage Mutant Ninja Turtles (2003) episode "Nano", a colony of Nanomachines are separated from the main group and create a body made from junk, which is found by a jewel thief who "adopts" it (seeing as it has the intelligence and personality of a child) and uses it to commit crimes. Eventually, as the nano-bots multiply and it gets stronger, the Turtles have to destroy it by dumping it in a vat of molten iron, but they're pretty bummed about it later:
    Michelangelo: I kinda feel sorry for the guy. He was like a little kid.
    Donatello: Too bad he had such a rotten father...
  • Transformers
    • It's debatable whether Starscream in Transformers: Armada even counted as a villain anymore by the time he had his Redemption Equals Death moment, but Megatron definitely counted.
    • Ditto for Scorponok in Transformers: Energon.
    • Also, Demolishor, although he got better.
    • Transformers: Prime:
      • The Decepticons got some of their members killed unceremoniously. Breakdown was eviscerated by Airachnid. And Dreadwing, who wanted to kill Starscream who zombified his brother Skyquake, was killed by Megatron for disobeying his order to stand down.
      • Additionally, several MECH members end up being killed by Silas as he views them as useless now he is a human-Transformer hybrid, just after they saved him of all things. It's pretty hard not to feel sorry for them in this case.
  • TRON: Uprising: Keller's a scientist forcibly drafted into the occupation to force them to mind control other programs. She chafes, and helps the Renegade stop her concoction before going on the run, with the Occupation force chasing after her. She spends an entire episode in a state of panic, trying all manner of options to desperately escape while trapped on a train, nearly dying at least twice, and Beck, sympathetic to her position, trying to recruit her. At the very end, cornered, she goes back to the Occupation with Paige promising her no harm, but not before covering for Beck so no one knows he's a Resistance sympathizer. She goes to back to the general, who welcomes her back, and kills her like every other minion who displeases him.
  • Wakfu:
    • Poor Nox. The real kicker is when Yugo chews Nox out for committing so many atrocities in the name of his delusions. Finally seeming to understand the truth, or that he never had a chance of seeing his family again, Nox breaks down crying. When the soldiers of Sadida show up to pass judgement on him, he doesn't put up a fight. Likely because, on top of everything else, Nox had managed to convince himself (and attempted to convince others) that it was okay to do any horrible thing in pursuit of his goals because it would all be undone when he finally succeeded. He'd get what he wanted and no one would really be hurt. But of course, it didn't work out that way. Then he teleports away and travels to the grave of his beloved family, whom he wanted to see again so badly that it was the key motivation for everything he'd done, and dies either by quietly killing himself or running out of power after he surrendered the Eliacube to Yugo and couldn't draw on its energy anymore. Take your pick on which is even more depressing.
      Nox: Twenty minutes? All that wakfu spent for a jump of twenty minutes in time? Two hundred years of researching and collecting wakfu for twenty miserable minutes?! NOOOOOO!
    • Though debatably less sympathetic (and definitely less anti-villainous) than Nox, Qilby himself is a pretty sad character. From birth he was involuntarily Blessed with Suck by the fact he and his dragon sister alone retain all their memories every time they die and reincarnate, making him slowly and increasingly go mad as he surpassed the Time Abyss threshold — developing a Lack of Empathy as he watched everything in the Krosmoz one way or another, sooner or later return to the dust from whence it had risen, while he and his siblings remain eternal. His other siblings either didn't recognise his problems or just couldn't be bothered to help him, which further detached Qilby from everyone and everything but himself and his twin. And when Qilby finally acts out twice by forcing his people to become Space Nomads so he won't be bored with eternity, what is his punishment? Imprisonment, exile? Nope — being thrown into a Blank White Void for eternity without his sister or anyone (or anything) else, which surely doesn't do anything to get him over his crazy before he comes back out after thousands of years wandering around in total, lethargic nothingness. He escapes his oblivion for a while and has something other than nothing around him again, only to get thrown right back in his former prison after his temporary reprieve, condemned once more to sobbing alone in eternal oblivion — but not before the very immortal twin he sought to reunite with, the only other being in the Krosmoz who he truly though he could rely on, has rejected him for going too far alongside every one of their people.
    • Oropo was born one of the Eliotropes, an Eliatrope-like species that was accidentally created by Yugo when he used the power of the six Eliatrope Dofus. His species went through numerous hardships, and they prayed to Yugo and the deities of the World of Twelve to help them only to be ignored numerous times. When the rest of the Eliotropes died, Oropo was left alone as the last remaining member of his species, with their power being given to him. Much of his sympathy is later thrown out the window when it's revealed that he instigated most of the series' conflict by making Ogrest depressed and indirectly killing Nox's family and then nearly killing Lady Echo when she exposed him. However, he slowly reminisces about his good times with his Brotherhood and dies along with Echo when the bomb he created explodes, with Echo holding onto him and them kissing each other. The fact that Yugo didn't even know of his or his race's existence makes it all the more heartbreaking when Yugo presumably mourns Oropo's death.
    • The majority of the Brotherhood of the Forgotten can be considered this. They're the demigod children of several major deities who were either neglected or forgotten about by their biological parents, with it being shown that they have ill will towards their parents. It doesn't help that Oropo took advantage of their misfortunes and manipulated them from the start. It's only when he reveals the stuff he did that they officially turn against him.

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