[[quoteright:311:[[Film/KingKong1976 http://static.tvtropes.org/pmwiki/pub/images/kong_dead_6058.jpg]]]]
[[caption-width-right:311:[[TearJerker/KingKong All he wanted was to be loved...]]]]

->''"Nature has a way sometimes of reminding Man of just how small he is. She occasionally throws up terrible offsprings of our pride and carelessness to remind us of how puny we really are in the face of a tornado, an earthquake, or a Godzilla. The reckless ambitions of Man are often dwarfed by their dangerous consequences. For now, Godzilla - that strangely innocent and tragic monster - has gone to earth. Whether he returns or not, or is never again seen by human eyes, the things he has taught us remain..."''
-->-- '''Steve Martin''', ''{{Film/Godzilla 1985}}''
%% One quote is sufficient. Please place additional entries on the quotes tab.

So, there's a villain. Right. Murdering, world-conquering type. The series is ending, so it's time to get rid of him. [[PayEvilUntoEvil Slowly and painfully.]] So he goes out with... a final touching quote and a OneWomanWail?

As odd as it may seem, if you want the audience to feel sorry for a villain, a good death scene is probably the way to go. This works best if you know their FreudianExcuse; [[LawfulStupidChaoticStupid Chaotic Stupid]] need not apply for this sort of thing. Also works best if this is a supporting villain. This is easiest to do with a BigBad's minions: we can identify with TheDragon, and especially the QuirkyMinibossSquad, over time and may be sad to see them go. If a FallenHero dies, expect everyone to [[ManlyTears weep openly]]. A few well-chosen LastWords may also be used to create this feeling.

Note that if you want the audience to take the scene seriously then it helps to add some humanizing elements to your villain beforehand. See LikableVillain for ways in which this can be done. Neglecting to do this may result in Narm or just confuse the audience.

Compare DracoInLeatherPants, CryForTheDevil, WhatASenselessWasteOfHumanLife, AntagonistInMourning, and DeathEqualsRedemption. See MonsterSobStory when the villain's death isn't required to garner sympathy. Do not confuse with AlasPoorScrappy. Or AlasPoorYorick for that matter.

'''As a DeathTrope, several if not all Spoilers will be unmarked ahead. Beware.'''


* AlasPoorVillain/AnimeAndManga
* AlasPoorVillain/VideoGames


[[folder:Comic Books]]
* Lord Zarak (A.K.A. Scorponok)'s death in ''Comicbook/TheTransformers''. This could seem to not count, since he was trying to stop Unicron, and therefore not dying in a villainous way, but remember that he was the Decepticon leader at that point.
* Moloch in ''Comicbook/{{Watchmen}}''. It was made more poignant because, on many levels, it had more to do with Rorschach than him. This part:
-->'''Edgar Jacobi:''' Heh. Well, you know that kind of cancer that you get better from eventually?\\
'''Rorschach:''' Yes.\\
'''Edgar Jacobi:''' [[TearJerker Well, that ain't the kind of cancer I got]].
* ''Comicbook/TheLeagueOfExtraordinaryGentlemen''
** Mr. Hyde singing "You Should See Me Dance the Polka" as he jaunts off toward the tripod is particularly emotional when it hits you that, for all his unbridled depravity, you'll never experience his brilliantly dark humor again. Throw in his unrequited love for Mina, and it gets exponentially more difficult to read.
** It's also a bit difficult not to feel bad for Moriarty, given the horrifying manner of his death.
* Asajj Ventress from ''WesternAnimation/StarWarsTheCloneWars''. She is given sympathetic qualities in the middle of the series, and her journey to sympathetic-ness is completed at the very end when her hero and mentor, Count Dooku, orders her shot to death because he can't be bothered to wait for her. She makes one last pitiful attempt to kill her nemesis, Obi-Wan Kenobi, and is cut down by Anakin. As she lays dying, she reaches out for Obi-Wan and tells him to watch the Galactic Core and Coruscant. Her final words finally reach this territory:
-->'''Obi-Wan:''' I thought you'd use your dying breath to curse us.\\
'''Asajj:''' Perhaps I have...or perhaps I just...hate Dooku more than I hate you....Or maybe...you were right about me...all along....
** Then, it's subverted when the medical ship that her body was placed aboard mysteriously vanishes, and it's revealed that, [[MadeOfIron terrible though her wounds were]], [[NotQuiteDead it takes more than that to bring her down]].
* When Destro was thought to have died in Marvel's ''[[ComicBook/GIJoeARealAmericanHeroMarvel G.I. Joe]]'' series, Snake-Eyes and Scarlett lay flowers at the place where he supposedly died.
--> '''Lady Jaye''': You fight somebody long enough, you get to know them... and after a while -- [[WorthyOpponent you start to respect them]].
* ComicBook/TransformersLastStandOfTheWreckers: The Decepticon Snare, The Predators security director, is stuck at G-9 under one of the most sadistic Decepticons ever, Overlord. Despite him, and many other troops, disturbed and uncomfortable with everything [[note]] As security director he oversaw the torture and death of many Autobots, making it hard to scare or upset him[[/note]], Snare throws a SpannerInTheWorks by freeing Impactor, and later leading some of the Autobot rescue team to save the rest of them. In the scuffle, he's shot and lays dying, asking Impactor to kill him before Overlord comes and finds what he's done. Impactor does so after thanking him.
* {{ComicBook/Batwoman}}: Abbot, the werewolf leader of the Religion of Crime Cult. Throughout the series he saves Batwoman at least twice (though is at odds with her because he's a criminal who withheld information about her sister and was part of the cult that tried to kill her) and leads his troops into battle against Medusa's forces. Despite being afraid of Medusa and her power, he still chooses to stand with Batwoman, and tries attacking Medusa from behind. Medusa catches him, petrifies him, and shatters his body. Batwoman looks at his remains sadly, and later uses a piece of mirror to give Medusa the same fate.
* {{ComicBook/Daken}}: The title character has done this twice. The first time, he broke down while dying, asking to see his father and apologising for placing a bomb at the Jean Grey Academy, before immolating himself with a bomb. The second, in which he inexplicably came back from the dead, involved him imagining how life could have been with his father and mother, had she not been murdered by Romulus. Wolverine is then forced to drown him to kill him, as by this point he is little more than a pawn for Sabretooth to use against him. Wolverine himself then breaks down, realising they could have had a happy life too. Considering Daken was TheSociopath most of the time... damn.
* After gleefully spending ''Comicbook/TheKillingJoke'' crippling Barbara Gordon and torturing her father James, SelfDemonstrating/TheJoker starts off the story absolutely evil, but his last few monologues leading up to his defeat transform him into a sympathetic lunatic who truly does believe life is cruel and pointless, and that all of Batman's attempts to redeem him are hopeless. Instead of his typical Batman beatdown, [[TearJerker/{{Batman}} he tearfully shares a joke with the Dark Knight, and the two of them actually laugh together in the rain while the cops arrive.]]
* ''ComicBook/KickAss'':
** John Genovese, sort of. Big Daddy drove him nearly to madness, and all because Big Daddy wanted to live his childhood fantasy and chose him as the villain.
** Chris Genovese, who dies saving Mindy and asking her to apologize to his mother for ruining her life.
* Comicbook/{{Thanos}} in the 70s crossover between Comicbook/TheAvengers and Comicbook/AdamWarlock. He's an OmnicidalManiac who wanted to destroy the entire galaxy to impress [[TheGrimReaper Mistress Death]], but is [[TakenForGranite turned to stone]] by Warlock. The last panel shows a tear rolling down his now-petrified face, mourning for his lost love.
* Discussed and subverted in ''Terra Obscura''. The Grim Reaper was once a great hero, but turned bad and ultimately died while attempting to assassinate some old friends for the mob. At the end of the first miniseries, he's buried with the other casualties of the story in a hero's graveyard, complete with a marble statue of himself for a tombstone. However, none of the heroes attending the funerals believe he deserves it -- it's just a political move to keep his actions from ruining their reputations.
* In the ''ComicBook/SinCity'' album ''Hell and Back'', Wallace feels some pity after he kills Deliah, the contract killer who tried to seduce and kill him, calling her a "strange, sad creature" before [[DueToTheDead silently closing her eyes]].
* The Crime Master in the end of Agent Venom's first volume. Not only does he get shot dead by ''his own sister'' but his last words, rather than swearing vengeance or cursing his enemies, are just this:
-->"[[IJustWantToBeSpecial I was meant... for... something special...]]
** Toxin gets a similar reaction from Venom mainly because he was forced into the role and died before Venom could save him.
* When the first Porcupine (Alex Gentry) died helping take down the Serpent Society, ComicBook/CaptainAmerica was deeply saddened by his old foe's demise and even insisted on giving him a memorial in the Avengers Mansion, a right usually reserved for longtime Avengers and worldchanging heroes. Given that Porcupine was a FriendlyEnemy to Cap at best and an IneffectualSympatheticVillain at worst this isn't terribly surprising.
* The Pride's demise at the end of the first arc of ComicBook/{{Runaways}}. [[WellIntentionedExtremist All the evil and bloodshed they did was to build a better world for their children]], (the heroes) and they're [[YouHaveFailedMe all unceremoniously slaughtered by the Gibborim]] after their plan fails. Special mention, though, goes to the Minorus, whose last act [[HeroicSacrifice is to take a final stand against the Gibborim to save the Runaways]], and the Yorkes, who sadly watch their daughter escape and reflect on their own descent into villainy.
--> "So this is what we're reduced to, eh, mother?"
--> "Yes,love. Empty nesters."
* {{Dick Tracy}}: The final arc featuring Big Boy Caprice had several of these. There's the explosion that claims the life of bomb-maker Little as his wife looks on in horror, the pathetic exit of a broke convict hoping to get rich by killing Tracy, and the death of the hired killer known as the Iceman, who was just starting to feel something for Sparkle Plenty. Perhaps the most depressing of all may be the death of Big Boy himself, who dies alone, abandoned by his henchmen, and cut off from all the power that once made him feared. Tracy may think Big Boy was a KarmaHoudini, but the audience isn't likely to agree.

* Though rare, it is not unheard of for this to happen with Voldemort in ''Literature/HarryPotter'' fanfic. One such fanfic used a spell to make Voldemort revert back to the boy he was before he became evil ({{handwav|e}}ing the fact that in canon, young Mr. Riddle was screwed from the beginning), and then [[TearJerker Harry held him and comforted him while the shock of all the terrible things he had done slowly killed him.]]
* Pretty thoroughly invoked in ''Go Not Gently''...somehow.
* Of all the villain deaths in ''FanFic/TheImmortalGame'', the only one that earns any audience sympathy is [[RoyalBrat Empyrean]]. He's only a villain because [[BigBad Titan]] forces him to, and [[IneffectualSympatheticVillain isn't even all that good at it]]. His mini-VillainousBreakdown when the Mane Six [[StormingTheCastle break into his throne room]] and [[BroughtDownToNormal strip him of his power]] is pathetic, and it's hard not to feel sorry for him when Titan shows up, [[YouHaveFailedMe decides he's useless without his powers]], and kills him while he begs his father for mercy.
* Several griffon soldiers in ''Fanfic/AceCombatEquestriaChronicles'', but especially Axe and Echo.
* The ''FanFic/PonyPOVSeries'' has a couple of examples:
** [[PhysicalGod Destruction]]. Despite being literally addicted to destruction, he was also the most sympathetic of all the draconequi, as he hated his addiction and wished he didn't have it at all. His desire in the war with the alicorns was to cause so much destruction he'd finally be rid of it once and for all. Him being killed and eaten by his own brother is extremely tragic.
** Also kind of hard not to feel sorry for the Master in the [[BadFuture Dark World]], who the Valeyard subjected to the same thing Discord did to the Doctor (namely, being [[FateWorseThanDeath killed repeatedly with him regenerating each time]]). What's worse, according to WordOfGod, the Valeyard's claim to keep killing him until he gets a good personality was just an excuse to kill him over and over again.
** Despite spending a thousand years massacring entire families with no remorse, following Discord's orders without protest, and generally being the biggest {{Jerkass}} in the Dark World, it's pretty hard not to pity Angry Pie when Twilight gives her a HUGE NoHoldsBarredBeatdown in "Cold Hoof Blues". By the end of the chapter, Angry Pie is crying and begging her foals to forgive her for failing to succeed in her task to bring them back to life. Even the other heroes (whom Angry Pie just tried to kill) are [[WhatTheHellHero shocked and horrified by Twilight's actions]]. Thankfully, they manage to talk Twilight down and she ultimately redeems Angry Pie with a reverse Memory Spell (showing her Twilight's memories instead of her own).
** Similarly, it's hard not to feel bad for Dark World Fluttercruel, even after all she's done, when he watches Discord get literally stabbed in the back by Rancor, which she simply cannot comprehend. She ends up crying and pleading with Discord to absorb her to heal himself. It shows that despite all else, she's still a foal who [[EvenEvilHasLovedOnes deeply loves her father]] and doesn't want him to die. What's she like by the end of the final fight with her? A broken little child who by that point knows her actions were wrong but is too driven by her UndyingLoyalty to her father to make a HeelFaceTurn.
* In the ''Fanfic/PonyPOVSeriesChaosVerse'' (a spin-off of the above), the death of BigBad Nightmare Phobia invokes this. In her final moments, she recovers her [[TheDarkSideWillMakeYouForget lost memories]] and realizes just how in the wrong she was. Her last act is to reach out to Celestia and Discord longingly before dying. Luna even mourns for her afterwards.
* ''[[http://www.fanfiction.net/s/7458771/1/Talen Talen]]'' is this for [[Disney/TheLittleMermaid Ursula]], and easily becomes [[{{Fanon}} Head Canon]] for those wondering how she grew up to become the movie's manipulative, power-hungry witch. (Hint: it involves a FreudianExcuse of FantasticRacism and an all-too-realistic case of AintTooProudToBeg.)
* FanFic/AGrowingAffection has a couple of cases.
** Karin gets just enough time to ask Sasuke for a fake show of affection. Sasuke gives her a real kiss, and she dies in the middle of claiming that he really did love her.
** After Gouki commits SuicideByCop, his last words are to hope that his wife will be able to find happiness in the new world. WordOfGod says he died without knowing she was pregnant.
* The immortal lion cub Shocker in ''[[Fanfic/TheLionKingAdventures The Lion King Adventures]]'' is a good example of this. Despite being a truly despicable character, his fate is rather harsh. He is buried alive, and, being immortal, is forced to choke on dirt for all eternity.
* ''FanFic/MegaManDefenderOfTheHumanRace'' has Ballade, who makes a not-quite heroic sacrifice in order to save a little girl trapped where he was ordered to detonate explosives.
* ''FanFic/{{Hivefled}}'': Dualscar was a slave-taking JerkAss who tried to have his ex murdered, but it's hard to imagine he did anything that would make him deserve the death he got.
* ''FanFic/YoungJusticeDarknessFalls'': Volcanna in this fic was a lustful fire wielding fury who caused nothing but trouble for the league and team, and had a rather [[StalkerWithACrush unsettling obsession]] with Superboy. However, her dying for her comrade Big Barda when they decide to desert the furies was a surprisingly touching moment, and her death was treated not with contempt but with sympathy.
* In the My Little Pony/Dresden Files crossover ''Fanfic/TheDresdenFillies'' False Masks, the ''entire Order Triune'' becomes this. They are sacrificed to a demon by Novel Notion. Considering they spent the whole story trying to kill Harry thinking he was someone who had been dead for 1200 years, endangered many lives, and betrayed the very kingdom they swore to protect, it is karmic. But it becomes tragic when you realize that they had been misled this entire time, [[WellIntentionedExtremist they genuinely wanted to protect Equestria]], and had been betrayed by one of their own. The way they go is also terrifying: running for their lives as the circle swallows them, with the pegasi who tried to fly away being swat down like flies. Afterwards, all that's left of them is some blood. The horrified reactions of the Mane 6, and even Harry seal this.
* In the supercrossover military fanfiction series, ''FanFic/TheTerminatorsArmyOfLegend'', the antagonist of Volume V, Zack Dawson, can be considered this. Even doubly painful considering his [[WeUsedToBeFriends relationship with series protagonist Alex Vaughn.]]
* In [[http://www.fimfiction.net/story/178650/dreams-about-friendship-are-magic Dreams About Friendship are Magic,]] [[spoiler: fake Celestia was disturbingly clingy to Twilight, and tried to keep in what was pretty much a coma for the rest of her life, but because she goes out sobbing pitifully, begging Twilight to be with her and telling her how much she loves her,]] it's esay to feel sorry for her.
* ''FanFic/FalloutEquestriaProjectHorizons'' does this with just about every antagonist, most of whom perform a HeelFaceTurn at some point.
* In ''FanFic/KillOrBeKilled'', [[spoiler:Taeyeon]]'s death. [[spoiler:She was only turned to darkness because she wanted to avenge Leeteuk's death, but it grew to the point where she had to be killed by one of her own group members to stop her. Right before she dies, the POV switches to her as she reunites with Leeteuk in the afterlife.]]
* In ''FanFic/TheLittlePonyLegend'', despite all the horrible things done by them, Korra genuinely mourns the deaths of Tarrlok and his brother, saying that [[spoiler: losing her bending]] was now the 2nd worst thing she experienced today.

[[folder:Films -- Animated]]
* In ''Disney/TheLionKingIISimbasPride'', [[WellDoneSonGuy Nuka]], TheUnfavourite, mostly just wants his mother to appreciate him. In the end, he dies trying to get her attention and fails even at that. He spends his last breath apologizing to Zira for failing, his death prompting one of the only displays of love and affection that Zira probably ever showed him.
* Kadaj from ''Anime/FinalFantasyVIIAdventChildren''. His death scene was a surprisingly effective a TearJerker for some.
* The Wolf Boss in ''WesternAnimation/KungFuPanda2'' carries out Lord Shen's plans without much mercy, but his death (stabbed by Shen himself [[EvenEvilHasStandards for refusing to fire]] [[WeHaveReserves on his own men]]) is really saddening.
* While Cobra Commander was always an ineffectual coward in ''WesternAnimation/GIJoeARealAmericanHero'', one can't help but feel for him in ''WesternAnimation/GIJoeTheMovie'' where he is lying on the ground, in agonizing pain, having been exposed to virulent spores that are mutating him into a snake, and [[VillainousBreakdown slowly losing his mind]].
* ''Disney/ThePrincessAndTheFrog'': Dr. Facilier spent nearly the entire movie trying to kill Big Daddy and enslave the souls of the entire city of UsefulNotes/NewOrleans as a goodwill payment to his [[DealWithTheDevil ''friends"]], and mode-locked Naveen into a frog, but if you don't feel even the least bit of pity for Doctor Facillier at the end of the movie, there is a worry you may not have a soul. He is, rather graphically, dragged into Hell by his shadow, screaming and begging the entire time. It's so bad that [[TheHero Tiana]], whom he just put in a LotusEaterMachine and is the indirect CAUSE of his death, can only watch in abject horror.
-->'''[[VillainousBreakdown I PROMISE I'LL PAY Y'ALL BACK!!!! I JUST NEED A LITTLE MORE TIME!]]'''''
* In the ''WesternAnimation/FantasticMrFox'', all the animals are saddened by the death of Rat, even Fox himself (who dealt the killing blow), despite his being the traitorous head of security for farmer Bean. Rat did manage to come to his senses in his few final moments when he revealed that he had turned traitor because he had become too addicted to the apple cider of Bean.
* ''Disney/WreckItRalph'': King Candy/Turbo's death. Granted he is an evil selfish asshole that only cares about himself but watching him fly into the coke volcano panicking while an epic farewell version of his theme plays in the background might get you to have a little sympathy for this Disney villain.

[[folder:Films -- Live-Action]]
* ''Film/KingKong1933'' and all of its adaptations give sympathy to the ape once it's dead with the final line, "Twas beauty that killed the beast."
* ''Franchise/PiratesOfTheCaribbean''
** ''Film/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl'': Barbossa falls with the final line "[[ImColdSoCold I feel... cold...]]" and mournful violins play as his crew realize they're no longer cursed- but also no longer immortal, and they're immediately taken into Navy custody to be executed by hanging. Koehler gets a final look of shocked, sad confusion as he comes back to life with a sword through his heart.
** ''Film/PiratesOfTheCaribbeanAtWorldsEnd'' gives us one for the Kraken, whose massive corpse stranded on a beach gets Captains Sparrow and Barbossa (both back from the dead) musing sadly about the end of an era it symbolizes, as well as for its master Davy Jones, stabbed through the heart and brokenly whispering the name of his lost love before he falls over the side of his ship and disappears into the maelstrom below.
--->'''Davy Jones''': Calypso...
* The title character of ''Film/KillBill'' goes out much like this when the Bride finally takes her revenge.
* ''Film/SpiderManTrilogy'':
** Norman Osborn/Green Goblin from ''Film/SpiderMan1'': "Peter...''don't tell Harry''..."
** Dr. Octopus in ''Film/SpiderMan2''. [[RedemptionEqualsDeath "I will not die a monster!"]]
* ''Film/TheProposition'': "You got me, Charlie. What are you gonna do now?"
* ''Film/{{Hook}}'' gets this in his [[http://www.youtube.com/watch?v=-wX6_qCCnPc last moments]], before the Lost Children wind up [[TalkingTheMonsterToDeath chasing him into]] the square where the Croc falls on him. Hook kind of spoils it, though.
* ''Franchise/{{Godzilla}}'':
** The American dub of ''Film/TheReturnOfGodzilla'' has [[DamselScrappy Raymond Burr]] reflecting on how this trope applies to Godzilla.
** In ''Film/GodzillaVsDestoroyah'', it's played again, this time ''far'' more successfully. By now, he's a bit of an AntiHero, though.
** The oft-maligned [[Film/{{Godzilla 1998}} 1998 American version]] also has a strong influence of this at the end.
** It goes all the way back to the [[Film/{{Gojira}} original 1954 film]] in which you see that Godzilla is a TragicVillain, and is as much a victim of the atomic bomb as everyone else. It makes his death at the end [[TearJerker all the more heart-wrenching.]]
** In the [[Film/{{Godzilla 2014}} 2014 film]], it's hard not to feel a bit sorry for the Mutos when the mother is mourning the death of her babies, especially when we see them meet and the father feeds a nuke to the mother and they nuzzle a bit before making the nest. The mother's anguished vocalizations manage to convey the message perfectly.
* ''Film/KillTheIrishman''. Real life Irish mobster Danny Greene tries to make peace with the Mafia and get out of the gangster business to [[RetiredBadass retire in Texas]]. But the Mafia wants his head. The orphan who had a tough life is eventually killed with a car bomb, still DefiantToTheEnd when he sees his killer, [[FaceDeathWithDignity point a gun finger at him]].
* ''Film/TheLordOfTheRings''.
** The series frequently shows Gollum's sympathetic side. His death is played for tragedy as he finally gets his greatest desire, only to be destroyed by the attempt.
** Wormtongue finally [[MistreatmentInducedBetrayal turns against Saruman]] and ''still'' gets shot by Legolas. This is after a MyGodWhatHaveIDone moment upon seeing the Uruk-hai, and ''without'' his involvement in the Scouring of the Shire from the books, which is what actually gets him killed in them.
* In ''Film/TheMummyReturns'', Imhotep is abandoned by Anck-Su-Namun -- for whom he essentially damned himself in the first place -- as he is desperately clinging to a ledge. For a moment, he can only stare at the O'Connells -- Evie having just rescued her true love, Rick, from the same situation -- with a look of absolute, crushing despair. Then, with nothing left to live for, he lets go of the ledge and allows what looks like the souls of the damned to drag him into the precipice. The novelization takes it even further. Rick, despite himself, actually tries to save Imhotep from falling into the abyss. Imhotep still lets go of the ledge, but not without a few parting words acknowledging that Evie and Rick's love for each other was the real deal.
* ''Film/BladeRunner'': The death of Roy Batty, leader of the rogue replicants. From his TannhauserGate death speech: [[RedemptionInTheRain "All those... moments will be lost in time, like tears... in rain.]] [[DramaticThunder Time]] [[CueTheSun ...to die."]] And [[DisturbedDoves one dove rises.]]
* ''Film/XMen'':
** Senator Kelly goes through absolute hell in ''Film/XMen1'' and renounces his anti-mutant beliefs before dying.
** In ''Film/X2XMenUnited'', halfway through [[spoiler:her death scene, the mind-control serum wears off and Deathstrike is allowed a few tragic seconds of clarity to realize where she is and what's happened to her; the look on her face says it all]].
* Khan, ''Film/StarTrekIITheWrathOfKhan''. It is absolutely tragic - a man who could've achieved so much, reduced to being so blinded by hate that he's willing to die just to see Kirk die with him, largely because of the death of his wife [[BackStory between his last appearance in Space Seed and this movie]].
* Shinzon from ''Film/StarTrekNemesis''. While not the best Trek villain, there's no denying that Shinzon's life ''sucked''. He was created solely to be a tool of war, and through no fault of his own, he was eventually condemned to a lifetime of back-breaking labor in a hellish mine (while a child, no less). And even though he managed to overthrow his captors and the entire Romulan leadership a decade later, his engineered lifespan ensured that he had a very short time to live. In short, he lived a short, violent, brutal life, and never really had any chance to know love or happiness.
* The Penguin in ''Film/BatmanReturns''. Even though he was a hideous psychotic sewer-dwelling monster, [[http://www.youtube.com/watch?v=S7zuMMuFjpA in his last few moments]], he comes off as quite pitiable, and his burial at sea by his own beloved penguins actually comes across as rather moving. It should've been {{Narm}}, but it somehow [[TearJerker worked]].
* Ironically subverted in Hitchcock's ''Film/StrangersOnATrain''. MagnificentBastard Bruno is dying, and for a second it seems like he is going to admit his guilt; instead, he uses his last breath to further accuse the protagonist in front of the cops.
* The eponymous character of ''Film/{{Blacula}}''. After watching his beloved Tina - the reincarnation of a woman he's waited centuries to see again - get staked through the heart, he deliberately walks out into the sunshine, [[DrivenToSuicide killing himself]].
* Dr. Frank N. Furter's last song, ''I'm Going Home'', and subsequent death is an example of this in ''Film/TheRockyHorrorPictureShow''.
* Robert Webber manages to turn his last scene in ''The Silencers'' into one of these.
* [[CrowningMomentOfFunny Hilariously]] subverted in ''Film/MotelHell''.
* William Foster in ''Film/FallingDown''. "[[HeelRealization I'm the bad guy?]]"
* Little Bill in ''Film/{{Unforgiven}}''.
-->"I don't deserve this. To die like this. I was building a house."\\
"Deserve's got nothing to do with it."
* Calvera in ''Film/TheMagnificentSeven'' goes out trying desperately to understand why. Much of the pathos comes from Eli Wallach being just that good.
-->"You came back. A man like you? [[EvilCannotComprehendGood Why?]]"
* The death of Riley Biers in ''[[Literature/{{Twilight}} Eclipse]]''. In his final moments, he calls out for his lover, Victoria, only for her to ignore him.
* ''Franchise/StarWars''
** [[RedemptionEqualsDeath Darth Vader's death]] is probably one of the most famous examples of this trope.
** The Rancor from ''Film/ReturnOfTheJedi''. A dancing girl and a guard already had the misfortune of being its lunch. Luke has to work hard to avoid being torn apart by this hulking beast, and the spectators are very surprised when he manages to kill it. Then the rancor's keeper bursts into tears and has to be led away.
* HAL 9000 in ''Film/TwoThousandOneASpaceOdyssey''. Despite being an apparently cold, logical computer AI who was willing to murder the crew of Discovery One, it becomes apparent why he did so: He was afraid. He did not want to be reprogrammed for making an error, which would essentially kill him. In the end, he is lobotomised while pleading for his life with the sole survivor (David Bowman), who ignores him. "Stop, Dave. I'm afraid. I am ''afraid'', Dave. Dave... My mind is going. I can feel it. I can feel it..."
* The Creator/StephenKing movie ''Film/{{Sleepwalkers}}'' looks like it's building to this, with the titular [[OurVampiresAreDifferent soul-sucking cat monsters]] constantly stalked by their weakness, and they're possibly the last of their kind. The young male Sleepwalker reads poetry describing their plight in class and seems to be falling for the female lead. A redemption plot looks all but guaranteed... And then when he tries to eat her soul, all the drama around whether or not he's falling for her vanishes and he becomes a gleeful monster with [[MoodWhiplash shocking speed.]]
* Vincent from ''Film/{{Collateral}}'' gives a rather saddening MeaningfulEcho just before he dies at the end of the film.
-->"Hey Max... A guy gets on the MTA here in L.A. and dies...think anyone will notice?"
* Both halves of the BigBadDuumvirate from ''Film/TheWorldIsNotEnough''.
* Gen. Francis X. Hummel from ''Film/TheRock''. The fact that he was actually an AntiVillain makes you feel even more sorry for him when he dies.
* [[StringyHairedGhostGirl Sadako Yamamura]], the DesignatedVillain from ''Film/TheRing'' series, suffers a lot even before she becomes a villain. She is raped in the novels, lost her mother in both continuities, beaten to death by angry actors, and then she bonded with her evil twin and kills all those who harmed her before, including her own innocent boyfriend, before being tossed down the well by her stepfather.
* In ''Ring 2'', Sadako appears before Mai Takano and Yoichi Asakawa as a ghost, asking why they can escape the well and yet she cannot, before allowing herself to fall back down into the well for eternity.
* Samara Morgan, the American version of Sadako in the American version of ''Film/TheRing'', suffers a lot too and is thrown down a well by her adoptive mother. This doesn't help, since her biological mother tried to drown her as a baby. And then she gets trapped in the well again at the hands of Creator/NaomiWatts.
* In ''Film/{{Skyfall}}'' Raoul Silva is a former MI6 agent, who was tortured to the point of severe facial deformity and hinted-at PTSD to keep their secrets. M (who left him for dead) admitted he was a "brilliant agent", and he himself has pulled a NotSoDifferent with James Bond. At the end of the movie, M has been mortally wounded, and Silva begs her to put the same bullet through their heads to end both their suffering.
* In ''Film/TheFaculty'', Casey kills the alien queen, Marybeth. As she is dying, he softly tells her, "You wouldn't have liked it here anyway.", acknowledging that -- despite being a monstrous parasitic alien -- she was just another outcast trying to find her place.
* In ''Film/LawAbidingCitizen''
** Aimes participated in a burglary. The plan appeared to be that his partner, Darby, would knock the adult occupants of the home to the floor with a baseball bat, then Aimes would handcuff them and then throw valuables from the home into a bag. Darby kills two people during the burglary while Aimes watches in horror and protests. Due to some legal technicalities and deals, Darby gets off easy while Aimes is executed. Aimes' last words: "What I did that day was wrong. But I'm not the one who killed those people. You're executing the wrong guy."
** Clyde Shelton, the man whose [[CynicismCatalyst wife and daughter were murdered by Aimes's partner,]] Darby. Beginning as a combination WoobieDestroyerOfWorlds and WellIntentionedExtremist, Shelton quickly [[JumpingOffTheSlipperySlope jumps off the slippery slope]] and has no doubt crossed the MoralEventHorizon by the movie's end. Despite how far he sinks, though, Shelton never fully loses the sympathy points gained from his family's murder, and even shows remorse for his crimes. In the end he [[FaceDeathwithDignity faces death with dignity]], sadly looking at the [[TragicKeepsake charm bracelet]] his daughter made for him in the beginning of the movie, seconds before being killed by one of his own bombs.
* The death of Mr Morton in ''Film/OnceUponATimeInTheWest''.
* The death of [[TragicMonster Prince Nomak]] in ''Film/BladeII'', who was driven to [[CallingTheOldManOut kill his father]] out of revenge for making him the first [[OurVampiresAreDifferent Reaper]]. In a final battle, he is stabbed in the heart and chooses to drive the blade in further to end his suffering. Tellingly, he does so [[GoOutWithASmile with a smile]].
-->"Strange … It hurts … It hurts no more …"
* In ''Film/AlienResurrection'', for all the murderous havoc the Newborn and it's entire race caused for Ripley, she's visibly sorrowful about having to kill it (and in an indirectly torturous manner at that).
* Willie Lopez and Carl Bruner in ''Film/{{Ghost}}''. The scenes of them being literally dragged into the netherworld (not to mention what is probably waiting for them once they get there) are pitiful and terrifying.
* It's hard not to feel a little sorry for the Emperor in ''Film/LegendOfTheBlackScorpion'' when he realizes he was just another pawn in the Empress's plan, and accepts death at her hands because "if it is your will, how can I refuse?" He dies in her lap.
* Subverted in ''Film/{{Scream 3}}'' with the movie's Ghostface Roman Bridger. While Ghostface is dying, Sidney holds his hand because he's her lost brother. Barely a minute later [[NotQuiteDead he gets up to kill them all again]] just when they were sure he ''wasn't'' superhuman. SlasherMovie psycho killers have to be shot in the head to put them down.
* Dr. Elsa Schneider in ''Film/IndianaJonesAndTheLastCrusade''. Indiana attempts to save Elsa when she causes a CataclysmClimax by trying to steal the Holy Grail. He manages to grab her before she falls into a pit; however, her obsession with the grail leads her to reach wildly for it. Indiana tries to hold on, but her hand slips from its glove and she falls to her death. After escaping the temple, Indiana looks back with an expression of regret that he couldn’t save her life. His father shows less sympathy when he says, "Elsa didn't believe in the grail. She thought she'd found a prize."
* General Garza from ''Film/TheExpendables'', [[RedemptionEqualsDeath who is killed]] as he undergoes a HeelFaceTurn and stands up to the true BigBad, Munroe.
* [[BigBad Viktor Cherevin]] from ''Film/JackRyanShadowRecruit'', especially when you find out that [[spoiler: [[YourDaysAreNumbered he has less than a few months to live]] due to his [[TheAlcoholic alcoholism]].]]
* General Zod in ''Film/ManOfSteel''. After losing everything he had due to his refusal to coexist with humanity, he soars across the DespairEventHorizon and commits [[SuicideByCop Suicide By Superman]] by forcing Superman into a situation where he has no choice but to kill Zod. After his death Superman breaks down out of remorse, having clearly wanted to find a peaceful solution.
* Andrew from ''Film/{{Chronicle}}''. Being subjected to [[AbusiveParents his Drunk Father's constant abuse everyday]], his neglectful cousin Matt paying little attention to him [[spoiler:until it's too late to save him]], constantly being bullied by everyone in his school, once he gets telekinetic superpowers you can only imagine what's on his mind. Needless to say, when the time comes for Matt to put him down before Andrew could destroy Seattle, he was extremely reluctant to do so.
* In ''Film/PeterPan'', at the very end, Captain Hook has just found himself right over the water, dangling above the crocodile with the last remnants of his fairy dust magic. Desperate to live, he starts thinking of all manner of things that make him happy while the Lost Children and Darlings repeatedly cheer "Old, alone, done for" to bring him down. Then, finally, Hook, sounding horribly depressed and weary, begins to repeat their chant, stops his flailing, and goes straight as he allows himself to fall into the mouth of the crocodile.
* The Saeki Family in the ''Film/{{Juon}}'' and ''Film/TheGrudge'', or at least Kayako, Toshio, and the cat Mar, who were all murdered by Kayako's husband Takeo under the false assumption Kayako was having an affair. Consumed by their own rage, they now haunt their former home and stalk and kill anyone who enters.
* In ''Film/RunAllNight'', [[spoiler: [[Creator/LiamNeeson Jimmy Conlon]] kills [[BigBad Shawn Maguire]], his old friend, and he lets him [[CradlingYourKill bleed out in his arms]].]]
* In a way, as everything Sheriff Teasle from ''Film/FirstBlood'' tried to do was to prove what Korean War vets are made of after being shunned for so long and to uphold the law in his duty as a policeman, yet now he's wounded in a pathetic state and is about to take more flak then he's ever before imagined.

* In ''Literature/DragonBones'' a minor villain is fed to a [[spoiler: basilisk]] by a more major villain. ''Alive.'' This is a fate no one deserves. The heroes think so, too.
* Count Olaf from ''Literature/ASeriesOfUnfortunateEvents'', one of the few cases where it works for the main villain.
* ''Literature/HarryPotter''
** Severus Snape. Okay, technically, to [[AlternativeCharacterInterpretation say whether he was a villain or not is debatable]] but still. Yes, he did have his reasons, but the audience didn't know that at that point in the story, and it was still a sad scene.
** [[WoobieDestroyerOfWorlds Barty Crouch, Jr.]] Sure, he became a death eater, but all he ever wanted was a loving father. Some fans thought that when he received the dementor's kiss, that his punishment was not only [[FateWorseThanDeath too far]], but also [[TearJerker very sad]], considering how neglected he was by his own father.
** Peter Pettigrew may be the most disgusting and loathsome character with no excuses, but you feel a bit bad that his own hand strangles himself to death because of his one moment of mercy for Harry.
* [[MagnificentBastard Grand Admiral Thrawn]] from ''Literature/TheThrawnTrilogy''. [[FamousLastWords "But it was so artistically done..."]] As the first major Imperial who was [[PragmaticVillainy ruthless and pragmatic]] but not outright ''evil'', he was always a fascinating character. Even his enemies couldn't help but admire him - an X-wing jockey once said, [[WorthyOpponent "I'd like to meet him, shake his hand. And then kill him, of course"]] - and his underlings adored him.
* Nearly every book in the ''Literature/{{Redwall}}'' series uses this trope, and half the time, it's the Big Bad!
* Martel's death in Creator/DavidEddings' ''Literature/TheElenium'' fits the bill. After three books of playing WorthyOpponent to Sparhawk, he admits he knew Sparhawk was better all along, and both Sparhawk and Sephrenia forgive him and give him their blessings. Just for a minute, the guy who betrayed the entire Pandion Order goes back to being Sparhawk's brother in arms again.
-->'''Martel''': You always said I'd come to a bad end, little mother, but you were wrong. This isn't so bad at all. It's almost like a formal deathbed. I get to depart in the presence of the only two people I've ever really loved. Will you bless me, little mother?
* ''Literature/TheBelgariad'':
** Zedar's fate in ''Literature/TheBelgariad'' makes one almost feel sorry for the guy. Sealed up in the ground, forever? Yeesh. Worse when you consider that his FaceHeelTurn was a result of being forcibly turned by the BigBad while trying to be the mole.
** Speaking of which, said BigBad also gets an Alas Poor Villain. Torak was a GodOfEvil, a {{Narcissist}}, and an utter bastard, but his death at the end, screaming for his mother as burning tears pour off his eyes after Garion [[TheReasonYouSuckSpeech takes away everything that matters to him]]? It's not pretty and it's acknowledged in-universe as such.
** The same could be said for Asharak, a high-ranking servant of Torak and manipulative bastard who messed with Garion for years, whose [[ManOnFire awful death]] will likely haunt Garion for the rest of his life.
** There's a retroactive example in ''The Malloreon''. [[TheBrute Taur Urgas]], King of Cthol Murgos was a [[TheBerserker frothing madman]], and was played as such in the ''The Belgariad''. In ''The Malloreon'' he comes off even worse as it comes out what life in his home was like for his children. Garion notes when talking about the terminally-depressed [[TheEmperor 'Zakath]] that he would much rather be fighting Taur Urgas ("now there was a man I could cheerfully have gone to war with. He polluted the world just by living in it.") And then Eriond points out that "he was insane, Garion, and that's not his fault." At that point, all of Urgit's comments about his father's fits of madness and irrationality come back to you in a whole different light, as you realise that the man was genuinely clinically insane, and not merely AxCrazy, and never got any help for it.
* ''Literature/WarriorCats'' has a tendency to do this with most of its villains, due to its GreyAndGrayMorality policy. Tigerstar, at least in the first series. Firestar notes afterwards that he could have been a great and noble warrior if he hadn't let ambition control him. The [[CruelAndUnusualDeath truly horrible death]] he suffered: being ripped open, and subsequently bleeding to death [[CatsHaveNineLives NINE TIMES]].
* The reader might not feel this way, but Rafen from Creator/JamesSwallow's ''TabletopGame/{{Warhammer 40000}} Literature/BloodAngels'' novels feels some sorrow when he sees the corpse of Sachiel. A nice {{foil}} to Sachiel's gloating over Rafen's [[NotQuiteDead (presumed) death]].
* From ''Literature/CodexAlera'', for all the horror she had caused, all the death and the near destruction of the world, the Vord Queen seems, in the end, to be a sad, lonely child seeking the approval of her father.
* ''Literature/RomanceOfTheThreeKingdoms'':
** Cao Cao gets a long poem on his death, daring anyone to criticize him.
** SmugSnake Yuan Shu dies as a result of some mixture of illness, starvation, and dehydration, all the result of his last botched campaign. His last words are a request for a little honey water for his throat, to which his chef replies that there is no water in the camp, save that which is tainted by blood.
* Many villains from ''Literature/MemorySorrowAndThorn'' by Creator/TadWilliams get this treatment.
** King Elias, despite playing the UnwittingPawn and being a complete JerkAss throughout most of the series, reveals that all the evil he commits (and abets) started with [[{{Necromantic}} grief over his wife's untimely death]]. At the very end, he [[ICannotSelfTerminate begs to be killed]] so he won't [[DemonicPossession become the host]] for the EldritchAbomination that the BigBad Storm King has become.
** Fengbald, the viciously amoral leader of Elias' army and the man [[RebelliousPrincess Princess Miriamele]] was going to be [[ArrangedMarriage forcibly married]] to, dies pitiably when he's caught in the trap of the {{Fake Defector}}s at the battle of the Stone of Farewell.
** Ineluki, the BigBad himself, is revealed to have committed all the atrocities in his life out of love for his people and a desperate desire to lead them to salvation. In the end, this realization leads directly to his defeat.
** Utuk'ku, the Norn Queen and TheChessmaster behind Ineluki's rise, is broken by the failure of the EvilPlan, and is left as nothing more than what she always feared to become: a frail old woman.
* In ''Literature/{{Otherland}}'', TadWilliams' next offering, the death of CorruptCorporateExecutive Felix Jongleur is suitably {{karmic|Death}} as his creation, the Other, [[TurnedAgainstTheirMasters turns his worst fears against him]]. However, given the glimpses the reader's allowed to see of his upbringing in a BoardingSchoolOfHorrors and how his entire adult life has been driven by fear of the AnthropomorphicPersonification of Death, it's hard not to feel sympathy for the poor tormented kid who grew up to be a bully himself, but died screaming in absolute terror.
* ''Literature/{{Dragonlance}}'' universe:
** A short story has Tanis and Flint kill a Black Mage who's been sucking the life out of people. After he's dead, they find out that he was doing it to prolong the life of his sickly son.
** ''Test of the Twins'': the Archmage Raistlin Majere attempted to become a god by dethroning one of the current ones. He manipulated everyone around him, abandoning or killing them as soon as they stopped being useful, and, as shown in an alternate would, have not only succeeding but have DESTROYED every other god in the pantheon, leaving him sole ruler of the universe. However, he sacrificed himself to save his time-traveling brother, ex-friend, and one of the people he manipulated, because they showed him that he would destroy the world in the process of attaining godhood.
* Several villainous characters by Creator/JohnCWright are pitiable when they die:
** ''Literature/WarOfTheDreaming'': Angelo Casselo, who ''knows'' he's nothing but a pawn in the game; and Manannan, alias Tom, a WhatMeasureIsANonHuman who had been desperately playing both sides in an attempt to prevent his people being annihilated.
** ''Literature/ChroniclesOfChaos'': Grendel Glum, who, for all his monstrousness, is merely a [[MarsNeedsWomen lonely]] [[DirtyOldMan old]] man, and Echidna, who is killed in the middle of her MamaBear rampage.
* Brandin in ''Literature/{{Tigana}}''. And he's the main villain too.
* Steadholder Mueller at the end of ''[[Literature/HonorHarrington Ashes of Victory]]'', simply because he was an UnwittingPawn.
* Almost every half-blood villain in ''Literature/PercyJacksonAndTheOlympians'' gets this in the final book.
** Luke tries to kill the heroes multiple times and tries to help the BigBad, Kronos, rise again (eventually hosting him in his own body). In the final chapters of The Last Olympian, he sees Annabeth bleeding, breaks free from Kronos's mind control, and realizes that he was fighting for the wrong side. He then kills himself to destroy Kronos, and it is indicated that he goes to Elysium in the afterlife.
** Ethan Nakamura fights in a battle to the death against Percy, and when Percy wins, he refuses to kill Ethan. Ethan repays him for this by betraying him and pledging himself to Kronos, enabling Kronos to rise again. Throughout "The Last Olympian", he is seen working for the Titans. Then, Percy convinces him to turn against Luke/Kronos, who kills him, earning him sympathy in the end.
** Silena Beauregard originally seems like a gentle, romantic daughter of Aphrodite. However, she is secretly a spy for Luke, and the information she has reported has lead to the deaths of many campers. When Kronos and his minions become responsible for the death of her boyfriend, she begins to think twice about her actions and eventually disguises herself as Clarisse, rallies the absentee Ares campers, and charges a Drakon, resulting in her death. Her secret - that she was the spy - comes out as she is dying, but the other campers remember her as a hero anyway.
* ''Literature/ThePhantomOfTheOpera'' -- Erik's death has this effect both on readers ''and'' on his fellow characters.
* In ''Literature/CityOfHeavenlyFire'', Sebastian Morgenstern goes down quickly, but Jonathan, the good within him, arises, tells Clary how to destroy the Infernal Cup, talks about what might have been, and then [[DeathEqualsRedemption dies.]]
* Creator/RobertEHoward's Franchise/ConanTheBarbarian
** In "Literature/TheSlitheringShadow", Thalis tortures Natala, but after the titular shadow swallows her up:
--->''She shuddered. "She [[ColdBloodedTorture tortured]] me — yet I pity her."''
** In "Literature/ShadowsInTheMoonlight" -- Shah Amurath
--->''Olivia closed her eyes. This was no longer battle, but butchery, frantic, bloody, impelled by a hysteria of fury and hate, in which culminated the sufferings of battle, massacre, torture, and fear-ridden, thirst-maddened, hunger-haunted flight. Though Olivia knew that Shah Amurath deserved no mercy or pity from any living creature, yet she closed her eyes and pressed her hands over her ears, to shut out the sight of that dripping sword that rose and fell with the sound of a butcher's cleaver, and the gurgling cries that dwindled away and ceased.''
* In ''Literature/{{Dracula}}'', Renfield's death invokes this trope. He's mostly unsympathetic for most of the novel--he nearly beats a man to death and attacks one of the protagonists with a knife--but when he realizes that Dracula had lied to him, he attempts to defend Mina Harker from him and is fatally injured because of it. The graphic description of his injuries doesn't help.
* In ''[[Literature/SkulduggeryPleasant Skulduggery Pleasant: Mortal Coil]]'', the death of the Russian assassin Tesseract. After being fatally injured by Lord Vile, Tesseract removes his mask and asks Skulduggery to help him get outside so that he can feel the sun on his face one last time. As they go, he talks about how he'll miss his cat, and how he has no regrets.
-->"I have a cat, you know. Back home. [...] She doesn't have a name. She is just Cat. She curls up on my chest whenever I sit down, and goes to sleep. I hope she doesn't miss me. I'm going to miss her."
* Mandrake is introduced in ''Literature/DunctonWood'' three chapters in as a bloodthirsty, giant mole that later becomes an iron-fisted dictator. Then, in a quick moment of Rebecca's life, he scolds her for enjoying the snow and, after that, delivers a speech against the snow that's quite poignant considering his story. And when he finally dies, he does so half-mad from wandering the Ancient System for months alone, crying for his only daughter while being mercilessly beaten down by a revengeful Stonecrop.
* Sly Moorcock from ''Stark'' by Creator/BenElton is a ruthless billionaire who has no qualms about leaving Earth with the other billionaires and letting humanity die in the inevitable ecological breakdown. Yet he moves more and more into AntiVillain territory as the story progresses, and shows himself in possession of both moral standards and the capacity to love, and when he commits suicide in the epilogue by throwing himself out of an airlock, it is just as sad as when one of the good guys die.
* In ''[[TabletopGame/ForgottenRealms Azure Bonds]]'', the red great wyrm dragon Mistinarperadnacles lays down her life to destroy the [[NamesToRunAwayFromReallyFast Darkbringer]] [[EldritchAbomination Moander]]. The heroes mourn her, and one of them, Akabar, notes that Mist's evil was fairly petty while [[RedemptionEqualsDeath she died saving the world]] from AFateWorseThanDeath. He even suggests that the group's bard should compose a song about her.
* Aurora in ''Literature/TheDresdenFiles'', the well-meaning but insane villain of ''Summer Knight'':
-->'Wait,' she said, her voice weak and somehow very young. She didn't look like a mad faerie sorceress now. She looked like a frightened girl. 'Wait. You don't understand. I just wanted it to stop. Wanted the hurting to stop.'\\
I smoothed a bloodied lock of hair from her eyes and felt very tired as I said, 'The only people who never hurt are dead.'\\
The light died out of her eyes, her breath slowing. She whispered, barely audible, 'I don't understand.'\\
I answered, 'I don't either.'\\
A tear slid from her eye and mixed with the blood.\\
Then she died.
** This is made worse when [[spoiler:it is revealed she was BrainwashedAndCrazy by an EldritchAbomination that drove her to this course of action]].
* In ''Literature/GoodOmens'', the demon Duke Ligur is doused in holy water in a booby trap set up by Crowley. He thoroughly deserved it, but for a demon, it's an amazingly horrible way to die, and his partner-in-crime Hastur immediately goes into VillainousBreakdown and attempts a RoaringRampageOfRevenge on Crowley, chasing him down a ''phone line''.
* Phoena's death in ''[[Literature/FirebirdTrilogy Fusion Fire]]'' was so horrific that Brennen did his best to comfort her in her last moments, despite the fact that not only was she responsible for his capture by the Shuhr, but she also tried to have him and his wife essentially tortured to death.
* The third ''Literature/{{Safehold}}'' book, ''By Heresies Distressed'', has this happen with Prince Hektor of Corisande. He's been beaten, he knows it, and he is preparing to negotiate terms of surrender with Emperor Cayleb. Before he can, however, he and his eldest son and heir are victim of an assassination that is blamed on Cayleb. Hektor, in his final moments, realizes that he truly loved his son, who had thus far been TheUnfavourite.
* In ''Literature/TheBartimaeusTrilogy'', Faquarl achieves the vengeance he's been craving for 5000 years, and discovers that it doesn't bring him the satisfaction he wanted. Then he finds Bartimaeus ''sharing'' a body with a human, proving him wrong about the inevitability of conflict between humans and spirits. Bartimaeus narrates that he's never sure if, had he wanted to, Faquarl couldn't have killed them before they shot him.
--> '''Faquarl:''' Your discovery is remarkable. But it comes too late for me.
* Literature/InDeath series: this has happened with some of the murderers after they get caught or killed. ''Portrait in Death'' has Eve and Peabody realizing that the murderer they caught wasn't greedy, vicious, or downright evil, just pathetic.
* ''Literature/TimeScout's'' Skeeter Jackson truly feels sorry for what happens to the enraged gladiator who spent the entirety of ''Wagers of Sin'' trying to kill Skeeter.
* Antrax in ''Literature/TheVoyageOfTheJerleShannara'' was just following its programming. Its reaction as it slowly loses contact with the outside world and shuts down is as sad as it is necessary.
* ''Literature/TheAeneid'': Most of the antagonists go out rather sadly. The standout may well be Mezentius, NayTheist, exiled tyrant, and brutal fighter whose disdain for the gods and vicious rule over his old city-state have brought him to Italy to fight as a mercenary. When his son and MoralityPet Lausus is slain, Mezentius goes ballistic, cutting down opponents left, right, and centre before being stopped by Aeneas; his FamousLastWords, wherein he refuses to pray and asks only that he buried by his son, are quite touching.
* Durza, the Shade from ''[[Literature/TheInheritanceCycle Eragon]]'', surprisingly earns sympathy just before his death at the hands of the protagonist. While fighting off the Shade's mental attacks, Eragon accidentally breaks through into his mind and sees a quick succession of images from his early life, before he became a Shade. The man who became Durza was originally a young orphan named Carsaib who was taken in by a sorcerer and instructed in the art. When his master was murdered, the grief-stricken young man called upon powerful spirits to get revenge, but they proved more than he was capable of handling and possessed him. Durza was pure evil, but Carsaib was a tragic figure who made a terrible mistake and paid dearly for it.
* Of all the characters who are involved in the FinalSolution of ''Literature/{{Timeline 191}}'' -- or at least all of the ones you get to know -- only Hipolito Rodriguez is still human and moral enough to have a HeelRealization and repent of what he has done. It's the sincerity of his horror and repentance that evokes sympathy.
* From ''Literature/{{It}}'', Patrick Hockstetter's death to some. Yes, he is a creepy and very disturbing [[TheSociopath sociopath]] who sees absolutely nothing wrong in doing things like [[MoralEventHorizon suffocating his baby brother and killing animals for fun]], but his death is so disturbingly horrifying and disgusting that it might be hard to feel any satisfaction over it.
* In ''Literature/TheStand'', the death of Harold Lauder. Presented as a fat, sometimes disgusting social outcast who uses overly purple language at times, is insanely jealous of Frannie Goldsmith, incredibly hateful towards the Free Zone Committee (and Stu Redman in particular, whom he believes stole Frannie from him), pompous, contrary and argumentative, Harold is nonetheless a tragic figure: sadly used by the BigBad, Randall Flagg, who takes advantage of Harold's weaknesses and literally leaves him to die by the side of the road with his leg shattered. Harold's final statement says it all: ''"I was misled."''
* In ''Literature/TheDarkTower'' there is the death of Trampas, one of the {{Mooks}} guarding the Devar-Toi. He works for the BigBad, but he's actually a pretty decent guy once you get to know him. It's made pretty clear that Ted really doesn't want to kill him and even yells at him to get out of their way, although he is forced to eventually resort to throwing a mind-spear at him, killing Trampas in the process.
* In ''LightNovel/FateZero'':
** Caster having a hallucination of Jeanne d'Arc reaching out to him while smiling and [[MyGodWhatHaveIDone realizing]] just what kind of monster he has become before dying.
** There is also Kayneth's death, based on your definition of "villain" (he ''did'' kill Risei). It's hard not to feel a little sorry for him when he gives up the War to [[PetTheDog ensure the safety of the woman he loves]], only to be ruthlessly gunned down together with her.
* The gamebook ''[[Literature/TimeMachineSeries Search for Dinosaurs]]'': A T-rex slowly starving in the aftermath of the meteorite fall is a rather pitiful sight, even if it tried to eat you previously.
* ''Literature/TheWheelOfTime'': [[HeelFaceDoorSlam Asmodean]] and [[LoveMakesYouCrazy Lanfear]]. [[TheDragon Ishamael]] could possibly be considered an inversion, as he [[DeathSeeker wanted to die]], and being resurrected was his punishment by the BigBad for his failures and insubordination.
* ''LightNovel/KaraNoKyoukai'': ''Overlooking View'' has [[IllGirl Kirie Fujou]], who unconsciously uses her spiritual counterpart to drive other girls into suicide out of loneliness. When Ryougi kills her spiritual counterpart, Kirie says that the moment Ryougi killed her was the most she has ever felt alive. Feeling she has nothing to live for and wanting to experience death again, she commits suicide.
** There is also Fujino Asagami in ''Remaining Sense of Pain'', although she's mostly an AntiVillain. She's been raped, her own father has hired Ryougi to kill her, and she's dying a slow, excruciating death via untreated appendicitis. At the end of the chapter, she's crawling through rubble, weakly repeating that she doesn't want to die between bouts of vomiting blood.
** Araya Souren in ''Paradox Spiral''. As he lays dying after Ryougi defeats him, Touko questions his obsession with the Spiral of Origin. Araya recalls his past and we see that witnessing endless death and tragedy has left him guilt-ridden over his inability to save the people around him in his years as a wandering Buddhist monk, so he decided to at least record their deaths and desperately attempted to find some form of meaning or purpose in them.
* Although the death of [[MadwomanInTheAttic Bertha Mason]] in ''Literature/JaneEyre'' leaves Jane and Rochester free to get married, it's hard not to feel for her, especially since her life has been so loveless and painful.
* ''Literature/TheLordOfTheRings'': Loathsome as Grima Wormtongue might have been, it's hard not to pity him when one sees the level to which he has been reduced by the time of his death.
* In ''Literature/TheDoomspellTrilogy'' by Cliff Mcnish the death of the first book's main villain Dragwena in the second book is really rather sad. The way she dies is rather horrible as she attempts to revive herself but CameBackWrong in a BodyHorror way. She also dies being cradled by her mother and sister who [[EvenEvilHasLovedOnes love her deeply]] and mourn her death.
* At the end of ''[[Literature/TheLegendsOfEthshar The Spell of the Black Dagger]]'', Overlord Ederd, having been restored to his throne, refers to Tabaea, the woman who overthrew him and seized control of the city and then died in a failed effort to save it (the city was saved, but not by her) as [[WoobieDestroyerOfWorlds "that poor girl" and "poor little Tabaea."]] It is clear that he means it.
* ''Literature/LesMiserables'' chapter [[ExactlyWhatItSaysOnTheTin "Javert In Disarray"]] is all about this, as InspectorJavert is DrivenToSuicide after his entire view of the world is destroyed by [[TheAtoner Jean Valjean]] [[SaveTheVillain saving his life.]]

[[folder:Live-Action TV]]
* ''Series/GameOfThrones'':
** Viserys' death, which is treated as rather pathetic and sad after the character's sneering villainy through most of the show.
** Doreah, who screams for forgiveness rather pathetically. Interestingly, the character's villainous actions were left on the cutting room floor, making it rather ambiguous as to whether she was a willing participant in the villainy. This, along with it being AdaptationalVillainy from the books (where she was good to the end), makes it all the worse.
** Despite being ''the'' go-to character for KickTheDog, Joffrey's death early in Season 4 is very poignant, especially the case of Cersei's reaction. Margarey also feels bad about the nature of his death.
-->'''Margarey:''' "Clawing at his own throat...looking to his mother to make it stop...it was horrible."
** Ygritte's death in Jon's arms during the Battle of Castle Black is ''crushingly'' sad, despite the character becoming very, very dark very, very quickly.
* ''Series/{{Smallville}}''
** Lex in the appropriately named "Requiem". Clark arrives and scatters his ashes in the wind after he is blown up by Toyman's bomb planted by Oliver.
** Davis Bloome/Doomsday in "Eternal", with Chloe crying next to him outside his cage. It would have been a bigger tear jerker if you don't know he is going to be back. By the time of his second death, he is a lot less sympathetic.
* From ''Series/DoctorWho'', The Master. [[JokerImmunity Repeatedly]].
** Also, [[LoneDalek that one Dalek]], from the episode of the same name. Never has the word "Exterminate" been uttered with such pathos.
** Cassandra in "New Earth".
** Oh man, that poor Krafayis from "Vincent and the Doctor", an ''invisible'' alien that ''kills a child'' in its first "appearance". Who gets the blame? Vincent. And yet, later, after Vincent manages to [[CrowningMomentOfAwesome fatally stab it with his]] ''[[CrazyAwesome easel]]'', we find out that this particular Krafayis was actually blind, and its supposed "attacks" were just fearful acts of self-defense, having been abandoned and left all alone on Earth by its pack (according to Eleven, it even gasps out "I'm afraid" repeatedly in its last moments). The Doctor realizes this as it's dying and tries to soothe it, [[CrowningMomentOfHeartwarming even though he can't even]] ''[[CrowningMomentOfHeartwarming see]]'' [[CrowningMomentOfHeartwarming it.]] Cue [[TearJerker tears.]]
** Yvonne Hartman, upon her final scene as one of the Cybermen, fighting off all the other ones.
---> "[[IDidWhatIHadToDo I did my duty for Queen and Country]]. [[MadnessMantra I did my duty for Queen and Country]]. [[TearJerker I did my duty for Queen and Country]]."
** The Minotaur in "The God Complex". Spent the whole episode "feeding" on the faith of those trapped in the hotel, but at the end, was revealed to be just another DeathSeeker.
--->'''Doctor''' ''(translating the Minotaur's grunts)'': "an ancient creature drenched in bloodshed" (...) "for such a creature, death would be a gift." Actually we find out, in the very next sentence, that it was referring to the ''Doctor'', but still... [[LonelyTogether it makes sense in the context]].
* ''Series/{{Angel}}''
** The villains go out this way from time to time, which is natural for a show that swims in the [[BlackAndGrayMorality Grey area]]. Nearly all the major antagonists get taken out this way, and it's up to the viewer to decide whether or not their fates were just. Darla, Lindsey, and Lilah each had ridiculously sad and depressing death scenes, while Holtz and Jasmine began to show signs of this trope, but would then yank it away by either setting into motion their [[ThanatosGambit own death]] or by tossing Angel off a bridge and then kissing him to screw with Connor, respectively.
** Holland Manners, as well. Sure, he was [[MagnificentBastard rather unrepentant in his actions]], [[TheChessmaster and his role in manipulating Angel]] led to a particularly KarmicDeath, but [[TheHero Angel's]] leaving him to plead for his life, about to be torn apart by Darla and Drusilla, was treated by Wesley, Gunn, Cordelia, and the audience as a stepping stone in our main character's MoralEventHorizon.
* Livia, the EvilMatriarch of ''Series/IClaudius'' was so pitiable on her deathbed that even Claudius, who knew her murderous nature well, was touched. [[TheCaligula Caligula]] on the other hand...
-->'''Caligula:''' And what makes you think that a filthy smelly old woman like you could become a goddess?
** Caligula himself died a rather pitiable death. It must be quite a shock to discover that you are not immortal after all.
** All the villains of ''Series/IClaudius'' qualify: Tiberius dies asking for lamb cutlets, Messalina frantically begs the soldiers sent to kill her not to take her head, and Sejanus (possibly the most despicable villain in the whole series) asks what has become of his children (both dead, and his daughter raped first because it was against Roman law to execute a virgin).
*** Even before their deaths, most of the fates of the villains invoke this trope. Thanks to his mother forcing him into a fate he never wanted Tiberius goes from being a stern but good general and loving, loyal brother to being a depraved, paranoid loner manipulated by Sejanus and filled with hatred for Rome and his own family. Livia becomes a lonely woman deprived of most of the political power she once enjoyed (and actually used well), having to live isolated with the memory that she murdered a man she genuinely loved, with the fact that her faith in her son, whose rise to the imperial office she dedicated herself completely toward, was tragically misplaced, and finally with her own terror of being punished eternally in the afterlife. Caligula devolves from an eccentric libertine to a madman who is cursed with the occasional moment of lucidity and in his delusions of godhood tortures and kills his sister Drusilla, the one woman he loved (while she's pregnant, no less). Sejanus is reluctantly pushed into abandoning his lover Livilla by his political ambitions, which despite his ruthlessness clearly hurts him and pushes Livilla even further over the edge. Messalina may be an exception, and even she obviously becomes increasingly unstable and unable to comprehend the risks she takes.
* ''Series/CriminalMinds'': [[FreudianExcuse poor]], [[MonsterSobStory poor]] [[SuperOCD Vincent]] [[AffablyEvil Rowlings]]. Made even more heartwrenching by his last dialogue with his MoralityPet:
-->'''Stan:''' (''Crying'') C-can we go around one more time?\\
'''Vincent:''' I don't think so.\\
'''Stan:''' I-I wish you were my dad.\\
'''Vincent:''' (''Last words'') Forgive me.
* Cassidy from ''Series/VeronicaMars'' was very pitiable when he killed himself. FreudianExcuse came into play massively.
-->'''Logan:''' Beaver, don't!\\
'''Cassidy:''' My name is CASSIDY!\\
'''Logan:''' Cassidy, don't.\\
'''Cassidy:''' Why not?\\
''[Logan can't say anything]''\\
'''Cassidy:''' That's what I thought.\\
''[He jumps]''
* ''Series/StarTrekDeepSpaceNine'': Weyoun. Yes, he dies several times. But a few of his deaths are very poignant, and very much ARE this trope. Particularly the one who became a defector, but was forced to perform a HeroicSacrifice to save Odo. After his [[KilledOffForReal final death]], the [[BigBad Female Changeling]] breaks her usual FantasticRacism to mournfully acknowledge him as "the only [[FantasticSlur solid]] I ever trusted."
* ''Series/StarTrekTheOriginalSeries'' had a few of these (in keeping with its avoidance of actually evil villains). One was Apollo (yes, [[Myth/ClassicalMythology that Apollo]]), who spent the episode trying to coerce and cajole the landing party into worshipping him so [[GodsNeedPrayerBadly he could survive]], all to no avail because Kirk and co. have OutgrownSuchSillySuperstitions and so, he fades away in a moment of [[TheWoobie Woobie]]-ness...
-->'''[=McCoy=]:''' I wish we hadn't [[IDidWhatIHadToDo had to do this]].\\
'''Kirk:''' So do I. They gave us so much. The Greek civilization, much of our culture and philosophy came from a worship of those beings. In a way, they began the Golden Age. [[WhatTheHellHero Would it have hurt us, I wonder... just to have gathered a few laurel leaves?]]
** Another was Dr. Richard Daystrom, whose MotiveRant about being laughed at behind his back and underestimated is legitimately heartbreaking. The fact that Daystrom is portrayed by William Marshall - an amazingly talented black actor who was undoubtedly kept out of roles by racism - adds an excruciating RealitySubtext.
** Flint from ''Requiem For Methuselah'', was not totally a villain but he has become somewhat misanthropic after 6000 years of life. To his credit, he was once Solomon, Alexander, Lazarus, Leonardo, Merlin, and Brahms. He has met Moses, Socrates, Jesus, and Shakespeare. He used Kirk's obvious attraction for Rayna in the hope that Rayna (an android he created) would transfer the resulting feelings she experienced to him. This failed miserably and she was torn between her love for the young, handsome captain, and her love for the kind old man Flint whom she considered like a father. This lead to her eventual death by short circuit. Throughout the encounter, Flint interfered with the Enterprise's mission to aquire a much needed cure for a plague, threatened the Enterprise crew, and tried to take them hostage. In retrospect, Kirk, emphasized with Flint who, while having shunned humankind, only wanted the company of someone who was his intellectual equal, even if he had to build her. Kirk, on the other hand, was far too easily attracted to Rayna and thus manipulated by Flint, which did say something about him as well. Kirk summed it up: "An old and lonely man...and a young and lonely man."
* ''Series/{{Dollhouse}}'' has a prime example of this in one of its final episodes, when Boyd is wiped, strapped up with explosives, and sent in doll state to destroy Rossum HQ. The doll stock line "I try to be my best" clinches it.
* The villain of ''Series/HarpersIsland'', Henry Dunn, is ImpaledWithExtremePrejudice by the protagonist Abby Mills, the girl he's in love with. OK, that love is [[BrotherSisterIncest creepy]] and [[StalkerWithACrush unwanted]], but he goes out professing his love for her.
* He's a certainly a lot less antagonistic than the other villains in the series, but Sano/Imperer's death in ''Series/KamenRiderRyuki'' is no less heartbreaking. In summary, Sano had finally attained a semblance of the happiness he'd always wanted, only to be betrayed by a man he thought was his friend and left to dissolve in the Mirror World with no hope of returning home. "I only wanted to be happy", indeed.
* In ''Series/KamenRiderKabuto'', we get the RichIdiotWithNoDayjob Tsurugi, who has thoroughly become a lovable comic relief character... until it's discovered he's really the Scorpio Worm. The real Tsurugi's over-the-top personality had over-riden the Worm's, essentially BecomingTheMask. While it seems like Tsurugi has betrayed humanity, even his potential love interest, it's actually all a part of a gambit to lead the Worms to ruin by following his orders. And it succeeds. Every Worm is defeated. [[TearJerker/KamenRiderKabuto Every . Worm.]]
--> '''Jiiya''': Master!\\
'''Tsurugi''': Hey, Jiiya?\\
'''Jiiya''': What is it?\\
'''Tsurugi''': Is it okay for me to dream?\\
'''Jiiya''': Yes! Don't worry about anything. Jiiya will always be by your side.\\
'''Tsurugi''': Thank you, Jiiya.
* ''Series/{{LOST}}'': The Man In Black. Once you learn his tragic backstory and motive, you can't help but feel sorry for the guy.
* [[InsaneAdmiral Captain Sawyer]] of ''Series/HoratioHornblower''. Cruel towards his lieutenants and especially [[TheWoobie Midshipman Wellard]], unstable, and antagonistic, but you can't help but pity the man who used to be a hero of the Nile. His death comes as both a relief and a tear jerker, especially as, directly beforehand, he had momentarily regained a shred of sanity, and he and Wellard had faced the escaped Spanish prisoners together with dignity.
* No matter what you thought of Shane Vendrell after he murdered Lem in Season 5 of ''Series/TheShield'', you can't help but feel sorry for him when he killed himself (and his family) in the series finale.
* ''Series/{{NCIS}}'': in-universe example: Ari. Ziva is clearly affected by killing him, she sings a song over his body and is haunted by it. Justified, they are half-siblings. The fans probably didn't feel the same way.
* Franchise/PowerRangers
** ''Series/PowerRangersLostGalaxy'': Scorpius was a creepy looking GalacticConqueror, but he genuinely loved his daughter, and his formal deathbed, with her in attendance, is quite sad. The deaths of {{Noble Demon}}s Loyax and Villimax also tugged at some heartstrings.
** In ''Series/PowerRangersLightspeedRescue'', Lokai is killed by Queen Bansheera, who [[PeoplePuppets forced Diabolico]] to fire upon the Rangers while he was fighting them. As he lay dying, Lokai lamented that all his years of faithful loyalty to the treacherous monarch seemed to be nothing but a waste.
** ''Series/PowerRangersSamurai'': Deker is freed of his curse after his final duel with Jayden, and is finally allowed to ascend to the afterlife after being forced to live with [[BloodKnight a hunger for battle]] for centuries. Even after all that he did in his battles against the Samurai Rangers; seeing him go was [[TearJerker genuinely saddening]]. Even more so Dayu, Deker's wife who was cursed alongside him and had to live with a beloved husband who no longer remembered her. At Deker's death, she fell into despair at her lost love and the years she spent pining for him. She then lost it, denying her human side and swearing utter loyalty to Master Xandred, who [[DevourTheDragon killed her and absorbed her body]]. At least Deker died ''happy''.
* Queen Beryl in ''Series/PrettyGuardianSailorMoon''. The real motivation behind her attempt at awakening Metaria and ruling over the world? She wanted to get back at Princess Serenity who always had everything she dreamed of: fame, beauty, power, and, most of all, Prince Endymion's love. 'Why do you... take everything away from me?'
* ''Series/BreakingBad''
** The Salamanca twins provide an interesting subversion. They go out in a [[CarFu particularly]] [[BoomHeadshot inhumane]] fashion and are still treated as the irredeemably evil force they have been up until that point, but that scene served as the climax to an episode that opened with a flashback to their FreudianExcuse.
** [[TakingYouWithMe Hector Salamanca]] (Tio) and Gus Fring in the Season 4 finale.
** Mike, if he even counts as a villain: He's getting out of the business and has kept Walt and Jesse in line as the OnlySaneMan in their operation, but winds up dead after angering Walt.
** Walt. [[TheAtoner His attempts at redeeming himself]], whether you think he succeeded or not, and [[MagnificentBastard the sheer awesomeness]] of his takedown of the Nazis and Lydia make his [[DyingMomentOfAwesome death]] even more devastating. His final conversation with Skyler, where he finally tells her and himself the truth, doesn't help either.
-->'''Walter:''' Everything I did...I did it for me. I liked it. [[BecauseImGoodAtIt I was good at it.]] I was, really...[[TragicVillain I was alive.]]
* Nick Cutler in ''Series/BeingHumanUK''. Especially after the flashbacks. He was just desperate for approval from people who treated him so horribly, including [[FriendlyNeighborhoodVampire Hal]]. In the scene where the Old Ones utterly cut him down his down his devastation is heartbreaking. Then he gets cooked.
* With the tendency for ''Series/TheAmazingRace'' teams to get a touching send-off after being eliminated or losing, even teams people originally rooted against can invoke this response upon realizing just how passionate they were about the race. The biggest example is probably Season 2's Wil, whose final speech has him tearing up and trying to figure out what he could have done better, while his ex-wife Tara celebrated with the winners, one of whom she had been flirting with for the entire season.
* ''Series/{{Charmed}}'': Lulu and Frankie, the ghosts who possessed Cole and Phoebe in "Paige from the Past". Despite being villains, you can't help feel sympathetic when it's revealed that their entire UnfinishedBusiness was simply wanting to get ''[[EvenEvilHasLovedOnes married]]''. Considering that they'd have likely moved on afterwards, Piper interrupting the ceremony comes across as kinda [[WhatTheHellHero a dick move]] on her part. Of course, sympathies are lessened somewhat by a line of dialogue that reveals that along with being robbers, they were also serial[=/=]thrill killers.
* Stringer Bell's downward spiral and death is seen as this by many fans of ''Series/TheWire''. Despite him being a murderous drug dealer who setup D'Angelo Barksdale's death and then had an affair with his woman afterwards, Stringer Bell was also shown as a thoughtful man who wanted to leave the life of crime and become a legal business man. He ends up getting screwed over by Senator Clay Davis when he tries to go legit, and his scheming finally catches up with him, to the point he can no longer talk is way out it. Finally, he decides to FaceDeathWithDignity.
* ''Series/{{Justified}}''
** The episode "Long in the Tooth" features Joe, a ProfessionalKiller for the Miami Cartel who is gunned down by Raylan while trying to make a deal with him. He manages to have a fairly lengthy conversation with Raylan before bleeding out, and it serves to humanise him.
** Mags Bennet, the BigBad of season two lives long enough to watch everything she worked her life for crumble. Her hometown despising her, her criminal empire going up in smoke, her two favored sons dead, her remaining living son in police custody, and the surrogate daughter she truly loved only barely being talked down from killing Mags herself, Mags opts to kill herself by drinking her poisoned moonshine. Her last words, a sincere echo of what she said to the man she killed with that very same moonshine, show just how far she's fallen into despair.
-->"Put an end to my troubles. [[TogetherInDeath Get to see my boys again.]] Get to know the mystery."
** Colton Rhodes, Boyd's [[TheDragon Dragon]] in season four. A former soldier in the U.S. Army, he had started out decently enough for a criminal, but steadily got worse and worse as his drug addiction took a bigger toll on him. Eventually, while in a revivalist church, he's caught by his nemesis, [[GoodCounterpart Tim Gutterson]], the friend of a man he earlier killed. Knowing the end is nigh, he decides to FaceDeathWithDignity. He lights up OneLastSmoke and apologizes to Tim for his friend's death, saying he believes the better part of Tim's friend died during the war, obviously using his victim as a [[SurrogateSoliloquy stand-in]] for [[ShellShockedVeteran himself.]] Finally, [[SuicideByCop knowing he'll die in the confrontation]], he draws on Tim, [[GoOutWithASmile smiles briefly after the bullets perforate him]], then collapses dead atop one of the church pews.
** Marijuana kingpin Rodney "Hot-Rod" Dunham in Season 5. Betrayed by Johnny Crowder, and held hostage by [[ThoseTwoBadGuys Jay & Roscoe]], Hot-Rod breaks loose and kills one of their men, only to take a bullet in the process. He's found moments later by [[TheHero Raylan]] and his own FriendlyEnemy Alex Miller, and chats with the two of them for a few moments as he bleeds out, reminiscing about the old days.
** [[TheBrute Danny Crowe]] of all people gets a send-off like this. While his death itself is meant to be BlackComedy, tripping and stabbing himself through the throat while trying to kill Raylan, the minutes before that, where he's mourning over the body of his dead dog, Chelsea, and tearfully recounting how he rescued him from a puppy mill, does a lot to humanize a man who had otherwise been a [[EvilIsDumb stupid]], [[AxCrazy psychotic]] [[{{Jerkass}} asshole]].
** Dewey Crowe, IneffectualSympatheticVillain extraordinaire and a mostly non-malicious ManChild, gets killed in the sixth season premiere. Returning to his old gang leader and [[WeUsedToBeFriends former friend]], Boyd Crowder, for work after he believes he received a sign from God, Dewey's outraged when Boyd uses him as a dupe in his latest plan. When he returns to Boyd, he laments the [[ButtMonkey constant abuses and humiliations]] he's suffered throughout the series, and tearfully professes a wish that things could go back to the way they used to be, back when they were Crowder's Commandos and he felt like he belonged with friends. Boyd tells him that things can never go back to the way they were, but shows Dewey a picture of his grandfather and a bunch of other men working as coalminers. He tells Dewey, no matter how much hardship they suffered, they still dreamed of a better future. [[LetThemDieHappy Boyd fills Dewey's head with hope that things could get better, just before shooting him the head while he's distracted]].
* ''Series/StargateAtlantis'': Subverted in "The Prodigal" with Michael. His fight with John Sheppard on top of the Atlantis main tower concludes with Teyla (who's most personally connected to Michael) and John throwing him off it. Michael holds on to the ledge and [[VillainsWantMercy screams at Teyla for mercy]]. By this point Michael had already committed galactic genocide, kidnapped and experimented on Teyla's people, mutated her husband into a monster, tried to harvest her baby at least twice, and tried to kill her and everyone in Atlantis out of petty spite. She kicks his hands and watches him fall to his death.
* ''Series/BoardwalkEmpire'': In the series finale, VillainProtagonist Nucky Thompson goes out like this. Despite committing progressively worse deeds throughout the series to maintain his power as TheDon of Atlantic City, one of the worst being [[spoiler:his murder of his surrogate son, Jimmy Darmody]], Nucky never lost all of his redeeming features. Throughout the final season, flashbacks showed his StartOfDarkness, how he UsedToBeASweetKid who came from a poor and abusive background, and how he craved both money and power as well as a loving family. The minutes leading up to his death are interspersed with one last flashback, of the moment he [[MoralEventHorizon metaphorically sold his soul]] by arranging the rape and resulting impregnation of a teenage [[BrokenBird Gillian Darmody]] at the hands of the pedophilic [[EvilMentor Commodore]] in order to become Sheriff. The self-loathing, pain and despair on the young Nucky's face is palpable even after he reluctantly goes through with the deed to get ahead. In the present, his greatest sin ends up the cause of his demise. After settling most of his affairs and about to go into [[RetiredMonster retirement]], he's confronted by Joel Harper, a young man he had tried to mentor. Joel reveals himself to be [[spoiler:Tommy Darmody, the grandson of Gillian and son of Jimmy]], who proceeds to fatally shoot Nucky in the same way Nucky killed his father. The last image of the series is a [[BookEnds Book End]] to the final season's opening moments, of a dying Nucky imagining himself as a child trying to catch a gold coin tossed into the ocean, only this time, instead of failing like he did in real-life, he manages to catch one.
* ''Series/TheOuterLimits1995'': Valerie 23 from the episode of the same name. She's a RobotGirl designed for love, then goes on a jealous rampage when she thinks that another human is taking the object of her affection away from her. When she's destroyed she acknowledges that she fears death, which the protagonist had earlier deemed is what makes something truly alive.

* In ''Manhua/RavagesOfTime'' every single dead villain receives at least a chapter as a eulogy, making Yuan Shu and Lu Bu look extremely sympathetic.

[[folder:Multiple Media]]
* Makuta Krika in ''Franchise/{{Bionicle}}''; he was the NobleDemon of the Makuta with a MonsterSobStory, who only went along with the plan of the Makuta of Metru Nui because he saw it as a "damned if you do, damned if you don't" scenario. He made a genuine effort to help the Toa (the heroes) at the end of the Karda Nui arc, and then, when he learned that the Makuta were about to [[YouHaveOutlivedYourUsefulness outlive their usefulness]], he tried to warn them, and was rewarded by slowly becoming so intangible that all of his atoms flew apart - the kicker of his death was that it was caused by his own power being forced out of control by his brethren, who thought he was lying.
* Music/{{Mothy}} loves this trope, especially in the Franchise/EvilliousChronicles.
** It is almost impossible to not feel sorry for [[HangingJudge Gallerian]] at one point or another. [[AdultFear His entire family was murdered]] because he didn't want to work with MA. He honestly believes [[ClockworkCreature the Clockworker's Doll]] is his daughter. And, at his death, there's an image of him hugging his 'daughter'. And later on, [[TearJerker it's stated that him protecting her from the flames was the only reason she didn't die.]]
** [[MonsterClown Lemy]]'s death. Despite him being an AxCrazy SerialKiller EnfantTerrible, the lyrics really hammer in that ''he was just a kid.''
--> Pierrot doesn't want to die! ''Pierrot doesn't want to die!''
** The titular duke from ''LightNovel/TheLunacyOfDukeVenomania''--despite everything he's done, it's hard not to pity him as he dies completely alone, abandoned by everyone; his harem, the woman he loved (realizing too late he loved her and being unable to voice it), and even the demon of Lust. [[spoiler: He reverts back to the ugly appearance that caused him so much abuse in his childhood afterwards, too.]]
** Margarita Blankenheim gets this in ''LightNovel/GiftFromThePrincessWhoBroughtSleep'', with Elluka trying to stop her from committing her misery-induced suicide. [[spoiler: Subverted when it turns out this didn't kill her after all, and Margarita's nature was much, much more sinister than originally thought.]]

* Subverted in ''Theatre/{{Oklahoma}}''. Curly tells Jud that when he dies, people will cry for him despite being afraid of him prior to his death. When he actually dies, what's the first song that they sing? "Oh what a beautiful morning…" Foreshadowed in the Curly/Jud duet ''Poor Jud is Dead''. Jud is really getting into this vision of how awful people will feel when he's dead, and Curly is echoing:
-->'''Jud:''' And folks are feeling sad that they used to treat him bad, and now they know their friend is gone for good.\\
'''Curly:''' Good.
* ''Theatre/RomeoAndJuliet''
** Tybalt. After all, the hero had just murdered him for what had ultimately been an accident. As this is Shakespeare, the validity of this is really up to the [[AlternateShowInterpretation director and]] [[AlternativeCharacterInterpretation the actor.]]
** [[RomanticFalseLead Paris]] would also be a good example. He's often displayed in a negative light, but ultimately, is simply a man trying to woo a girl he's in love with in the typical fashion of that era, and he's killed while trying to arrest a dangerous criminal who had killed the cousin of the woman he loved, and, for all he knew, drove her to suicide.
* [[InspectorJavert Javert]] from ''Theatre/LesMiserables'' gets sent off with an absolute [[TearJerker/LesMiserables Tear Jerker]] of a song, after having his entire worldview shattered.
* ''Music/JesusChristSuperstar'': "So long Judas, poor ol' Judas." [[SarcasmMode (You could interpret it as mockery, though.)]]
* ''Theatre/{{Macbeth}}'': As a Shakespearean tragedy with a VillainProtagonist, this is a given.

[[folder:Visual Novels]]
* ''VisualNovel/UminekoWhenTheyCry'': Beatrice falls in this trope. She starts the series as a witch who loves to kill Battler's family in the most [[CruelAndUnusualDeath horrifying ways]], but in [=EP5=] it's confirmed that she didn't actually enjoy doing this, and in [=EP7=] you are shown just [[ParentalIncest how Beatrice came to be]]. After she's broken, Bernkastel keeps playing with her.
* All of the murderers in ''VisualNovel/DanganRonpa'' are presented this way immediately before their execution. Most of them are portrayed as a SympatheticMurderer.
* Godot's defeat in ''VisualNovel/PhoenixWrightAceAttorney: Trials and Tribulations'' could count.
** Acro's defeat as well, with his remark (that you have to interpret for Regina) about how he wanted to stick around. He's worried that he might be in prison or executed by the time his brother gets out of his coma.
* Caster in ''VisualNovel/FateStayNight'''s "Unlimited Blade Works" scenario. Yes, she captures and tortures Saber, holds Taiga hostage, and is responsible for many a Bad End in Unlimited Blade Works, including one where she ''orders Shiro's friend, Issei, to kill him''. Yet her last moments were so touching, it almost made you forget all that.
** Kirei Kotomine in ''Heaven's Feel'', even more so. His actions in the route, and the backstory it reveals, does an impressive job of building sympathy for him, considering that he lives to see others suffer and is actively trying to destroy the world. Seeking the reason for his twisted existence, he died without regret. No wonder Shirou realized that he liked Kirei.
** Zouken Matou. It's difficult to feel sympathy for the monster he's become, but you might just pity the idealistic Zouken Makiri, who kept seeking immortality so that the woman he loved wouldn't have died in vain.
** Ilya, who in 'Fate' was a psychopathic monster at worst, appeared in 'Unlimited Blade Works' long enough for a tearjerking finale with backstory that managed to woobify her without even giving away her whole FreudianExcuse (which was saved for 'Heaven's Feel'). And Berserker, already DeaderThanDead from his SelfDestructiveCharge, managed to stand long enough to give her comfort before both died.

* In ''Webcomic/TheOrderOfTheStick:''
** Miko Miyazaki's [[SanitySlippage slide]] from holier-than-thou KnightTemplar to a TautologicalTemplar has her [[JudgeJuryAndExecutioner murder her lord]], lose her Paladin powers, and accidentally kill herself in fulfilling what she had decided was her divinely ordained destiny. The ghost of her order's founder tells her that her efforts were... [[DamnedByFaintPraise adequate]]... but not worthy of redemption, which she accepts with uncharacteristic grace [[http://www.giantitp.com/comics/oots0464.html as she dies]]. It's still debated whether she deserved it.
** In [[http://www.giantitp.com/comics/oots0830.html strip 830]], it's ''really'' hard not to pity Tsukiko -- an unrepentant CardCarryingVillain who [[TheQuisling sold out her own city to Xykon]] -- when Redcloak usurps control over her wights, who she'd treated like her own children, to prove that undead are little more then automatons for necromancers of any stripe. And then he has them drain her to death. And then eat her. She was a sick, twisted, self-confessed necrophiliac who was obsessed with ''Xykon'' because [[FreudianExcuse every living person she ever met in her entire life treated her like crap.]] What puts her solidly in Alas Poor Villain territory is that ''she really and truly loved him'', and only died because she discovered concrete proof that Redcloak is manipulating Xykon, and that the MacGuffin they're after won't get Xykon the power he wants. The point really gets hammered home when the only person to mourn is the Monster in the Darkness, who points out that in the end, Tsukiko just wanted to be loved.
--->'''Demon-roach:''' So what? Who cares?\\
'''Monster in the Dark:''' [[RhetoricalQuestionBlunder Exactly]]. That's why I'm sad.
** Nale's death in [[http://www.giantitp.com/comics/oots0913.html 913: Independent]] has caused some of these reactions. Nale is a petty, selfish mass-murderer, but hearing his anger about being treated like a tool by his father, and refusing his father's help to his face shows that he has balls, only to get stabbed by his own father. Plus Elan's reaction...
** Subverted when a reanimated Crystal is [[http://www.giantitp.com/comics/oots0981.html dumped into lava]]: three panels of silence, followed by brunch.
* Whenever Oasis dies in ''Webcomic/SluggyFreelance'', it's treated with sadness, even when she's been in full-on AxCrazy, StalkerWithACrush mode, since we know she's only like that because Dr. Steve {{Brainwashed}} her. However, as Oasis becomes more heroic and we learn she'll always [[DeathIsCheap come back]] from being killed, this has faded.
* The [[VillainProtagonist entire]] [[KillEmAll cast]] of ''WebComic/TheLastDaysOfFoxhound''. Except [[SociopathicHero Mantis]] and [[StayingAlive Ocelot]].
* ViolentGlaswegian Dougie in ''Webcomic/WhatTheFu'' suffers a breakdown from the revelation that he's not actually Scottish. Zac almost feels sorry for him, except he's "still a murderous psychotic bastard".
* ''Webcomic/{{Homestuck}}'':
** [[TheSociopath Vriska Serket]], who had spent the entirety of Act 5 Act 2 getting closer to [[TheHero John]] and finally admitting that she wanted to try living a normal life. She was killed by Terezi in order to prevent her from fighting Jack, which in an alternate timeline got everybody except Vriska and Aradia killed. Her final message? Telling John that if and when they finally do meet, she'd like to go on a date.
** [[IneffectualSympatheticVillain Courtyard Droll]], Jack's clueless underling who fails at being evil, which gets his superiors pretty annoyed with him. When he finally manages to follow one of Jack's orders to the letter (Jack had ordered him to kill Jade, something Jack himself couldn't do due to his UndyingLoyalty from Bec's prototyping), Jack snaps and kills him. Thankfully [[ResetButton the Scratch]] brings him back. [[AlternateUniverse Sort of]].
** Snowman is a {{Jerkass}}, but it's hard not to feel bad for her when the Doc Scratch-influenced Spades Slick shoots her dead at the end of Act 5, especially since she had [[JerkWithAHeartOfGold just saved his life]] a few moments before.
* In ''Webcomic/OurLittleAdventure'', in universe, [[http://danielscreations.com/ola/comics/ep0166.html the body gets dump with the epigraph: You poor, stupid kid.]]
* Ephsephin from ''Webcomic/{{Unsounded}}'', an IneffectualSympatheticVillain who [[TheChewToy suffers more and more abuse as the story goes on]]. He becomes even more sympathetic when WordOfGod says he was a failure at life who was obsessed with over how he couldn't provide a better life for his [[EvenBadMenLoveTheirMamas mother]]. The only reason he signed up with Starfish was to get a big enough payoff so that she wouldn't have to keep breaking her back working. After he gets grievously wounded by Jivi and begs Starfish for a doctor, [[DissonantSerenity Starfish merely smiles]], then bashes his head in with a whiskey bottle.
* Tobun in ''Webcomic/PennyArcade'''s Cardboard Tube Samurai storyline, is implied to have become a DeathSeeker after being compelled to commit atrocities. Fighting the CTS hand to hand, his last words are "before this moment, did I ever see the world?"
* ''WebComic/DragonBallMultiverse'': The first Cell Jr's death by his own father's hands. Especially after he had a HopeSpot of becoming more powerful.
* At the grand finale of ''WebComic/ErrantStory'', Ian just [[http://www.errantstory.com/2011-11-07/5323 keeps]] [[http://www.errantstory.com/2011-11-14/5324 repeating]] "I just wanted to help." Despite a personal body count in the ''thousands'', he's quite serious. However, it doesn't keep him from getting his brains blown out.
* Apple Bloom in ''Webcomic/MoodyMarkCrusaders''. Even though she's a jerk, it's hard not to feel sorry when she's TakenForGranite. [[spoiler: She gets better though.]]
* Kalki in ''{{Webcomic/Drowtales}}'' spends the majority of her screentime either acting like TheFakeCutie or inflicting serious harm or brutal deaths on other characters, including stabbing the hand of her own half-sister and nearly killing her by chopping off her arm ''the very first time they meet'', but the way [[spoiler:her mother Snadhya'rune]], whose neglectful parenting was at least half the reason she became as twisted as she did, coldly kills her and tells her she has [[YouHaveOutlivedYourUsefulness outlived her usefulness]] firmly puts her into this.

[[folder:Web Original]]
* Happens quite often in ''Roleplay/SurvivalOfTheFittest'':
** [[AntiVillain Bobby Jacks']] death, committed after realising the path he took. [[http://s10.zetaboards.com/SOTF_V2/topic/603213/1/?x=50#post908073 Read it here.]]
** [[PsychoLesbian Laeil Burbank]] goes out with a fairly tragic death, accented by how violently and sadistically she received her fatal injury and how she was almost saved. [[http://s10.zetaboards.com/SOTF_V2/topic/603240/1/?x=75#post909270 Found here.]]
** Clio Gabriella gets a fairly touching send-off, dying in her boyfriend's arms while she begs for him to save her after being shot. [[http://s10.zetaboards.com/SOTF_V2/topic/7314950/1/?x=50#post8734949 Again, readable here.]]
* In the tradition of its [[Franchise/MetalGear source material]], ''FanFic/{{Stray}}'' does this for one of its villains - the TykeBomb Patriot agent Esau.
* ''Series/{{Mega 64}}'' Version 3 ends with the legitimately tragic death of Dr. Poque, who started the series as the main antagonist.
* In the ''Roleplay/GlobalGuardiansPBEMUniverse'', the villain Hardcase was generally thought of as a brutish, selfish thug who liked to beat up women for fun, drank too much, and was generally a sleaze. And on September 11, 2001, he gave his life by using his superhuman strength to save people from the collapsing North Tower of the World Trade Center. The heroes not only campaigned to get him a posthumous presidential pardon, they sprang for a funeral the likes of which are normally reserved for deceased presidents and popes.
* CT in ''Machinima/RedVsBlue'' (no, not the one from Season 7, the real Freelancer who the Rebel Leader took the identity of) was never really a villain in the first place, but instead ended up becoming a HeroAntagonist to try and take down the Director. Her reward for trying to do the right thing? A throwing axe to the chest which mortally wounds her, causing her to die in her lover's arms.
** The Director also got a moment like this in the finale of Season 10, when he realised he should have spent more time looking after his daughter Carolina, realises that he has been chasing at ghosts futilely for several years, asks Carolina for a pistol, makes peace with her and F.I.L.L.S and then is implied to commit suicide.
* Scion of ''Literature/{{Worm}}'' was unquestionably a sadistic, OmnicidalManiac, but the way that Taylor defeated him by taunting him with the death of his counterpart makes it hard not to pity him.
* Although a lot of the villains in ''Machinima/ArbyNTheChief'' are usually downright [[{{Narm}} over-the-top]] like Craig, or downright [[HateSink hateful]] like Adam, the series's final villain, Eugene Black is certainly an interesting case of this. As evident throughout the show's final season, he's a downright sadist who has no trouble letting his psychopathic or pedophile friends do as they wish to people online, as well as enjoys forcing hundreds of innocent people to replace their Xbox 360s after banning them with a hardware corrupting software over a period of 2 months, [[ForTheEvulz just for laughs]]. On the flipside though, he's also a failing student at his school (despite [[JerkassWoobie also being a bully too]]), [[AbusiveParents is constantly abused by his Drunk (and sometimes neglectful) Father]], and his sister (the only source of happiness in his life) is dying a slow and agonizing death of Leukemia. It's hard whether to feel sorry for him for how crappy his life is, or to hate him for how much of a bastard he is just to repress these feelings. [[spoiler:To add insult to injury, this only get worse for him, and he's DrivenToSuicide by the show's end]].
* ''WebVideo/AskThatGuyWithTheGlasses'' goes out with a strange mix of this and DeathAsComedy. In the GrandFinale, someone asks him "do you have a question?". He gets so excited that someone finally thought about what ''he'' wanted that he literally explodes. {{Lampshade|Hanging}}d by Chester A. Bum, who is sad when he first finds out about That Guy's death, but then realizes that he was a terrible person and it's probably a good thing he's gone.

[[folder:Western Animation]]
* In ''WesternAnimation/BeastMachines'', 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.
* ''Franchise/{{Transformers}}''
** It's debatable whether Starscream in ''Anime/TransformersArmada'' even counted as a villain anymore by the time he had his RedemptionEqualsDeath moment, but Megatron definitely counted.
** Ditto for Scorponok in ''Anime/TransformersEnergon''.
** Also, Demolishor, although he got better.
* This happens ''[[TearJerker/{{DCAU}} a lot]]'' in the Franchise/{{DCAU}}.
** In nearly every [[AntiVillain Mr. Freeze]] appearance (except the one where he finally gets [[ThrowTheDogABone a happy ending]] and the one from ''The New Batman Adventures''), he is defeated in a tragic and {{Tear Jerk|er}}y way, culminating in this final exchange in his last appearance (both in RealLife and in the Universe timeline), where he lets himself be caught in a collapsing building.
-->'''Batman (Terry)''': Freeze, you have to get out of here! The whole place is coming down!\\
'''Freeze''': Believe me... you're the only one who cares.
** Solomon Grundy in a single episode (or rather two connected ones), goes from regular villain to sympathetic villain, who [[http://www.youtube.com/watch?v=OFoPc52Kd8I dies in his quest to attain his lost soul]]. For good measure, he's brought back again in a later episode, this time truly soulless, and has to be put down ''Film/OldYeller'' style.
--->'''Grundy''': Do you think... Grundy's soul is waiting for him?\\
'''Hawkgirl''' (A confirmed atheist): Grundy, I don't belie- (stops herself) ''Yes.'' It's waiting for you.\\
'''Grundy''': Then Grundy... gets his reward.
* ''WesternAnimation/{{Gargoyles}}''
** Though she doesn't actually die there, Demona's defeat at the end of "City of Stone" certainly counts, as a broken Demona, [[IgnoredEpiphany for a brief moment]], realizes and regrets the evil she's done over her thousand-year life, and then gives the heroes the password they need to shut down her scheme. It doesn't hold, but for a moment, you stop hating her and just feel sorry for her.
--->'''Demona''': The access code is… 'alone'.
** There's also the Captain, who was so wracked with guilt that he spent the next thousand years haunting the castle's remains after his death. Hakon was also haunting the site, but out of continued hate for Goliath (who ironically had nothing to do with either of their death's [[DisneyDeath 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 [[IndianBurialGround ancient ritual site]] where they can exchange his life for theirs. The Captain [[MyGodWhatHaveIDone realizes what evil he is about to commit,]] repents, and uses his brief physical form to destroy the site. With his last moments, he thanks Goliath for forcing him to acknowledge his sins and begs for forgiveness as he travels to the afterlife. This is such a CrowningMomentOfAwesome that Goliath happily mourns him as a friend who is finally at peace. [[FateWorseThanDeath Hakon is still stuck, trapped within the ruined site, alone to wallow in his hate.]]
* Hard not to feel a little bad for Azula by the end of the finale of ''WesternAnimation/AvatarTheLastAirbender''. You may remember her from works such as that time she [[ShockAndAwe fried Aang]], that time she inexplicably gave Zuko credit for it, or that time she ruined an invasion -- [[BroughtDownToBadass without firebending]] -- using only her natural skills in acrobatics, [[ManipulativeBastard taunting, and sarcasm]]. [[VillainousBreakdown The past few weeks haven't been so good]]; she [[BackstabbingTheAlphaBitch lost all her friends]], she got [[DaddysLittleVillain rejected by dad]], [[ParanoiaFuel she banished all her servants]], she [[ImportantHaircut chopped off a bunch of her hair]], she [[SanitySlippage hallucinated her mother]] simultaneously [[MachiavelliWasWrong shattering her worldview]] and saying she loves her, and she lost to her [[FailureHero loser brother]] and a peasant. Once an [[TheVamp irresistibly sinister]] and [[TheChessmaster brilliant]] prodigy, she is left [[BreakTheHaughty chained to the ground]], [[AxCrazy madly]] [[TheWoobie wailing, sobbing,]] and [[PyroManiac breathing fire at the sky]]. Well, [[FateWorseThanDeath at least she can still firebend]].
** In ''WesternAnimation/TheLegendOfKorra'', 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. [[TearJerker 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.]]
** Book 3 gives us...''every'' member of the Red Lotus inner circle except [[BigBad Zaheer]]. Even if someone's ''that'' much of a [[ColdSniper deadly]] [[BloodKnight ruthless]] [[PersonOfMassDestruction bastard]], being stuck in a TailorMadePrison (two of which were ''hellish'') for thirteen years is bad enough ''without'' ending up [[YourHeadASplode obliterating oneself]] via the [[PlayingWithFire pyrokinetic]] equivalent of a [[HavingABlast shaped charge]], being [[HighVoltageDeath electrocuted]], or [[DrivenToSuicide dropping a cavern on oneself]] to avoid [[IDieFree ending up back in the aforementioned cell]]. (Add to ''that'' the fact that [[TragicVillain one of them]] was a former [[ChildSoldiers child soldier]].)
*** Before that, we have one of the Red Lotus' victims: The Earth Queen. She was a selfish, probably insane despot who was foricbly conscripting neophyte airbenders into her personal army. And then she's murdered by Zaheer bending the air right out of her lungs. Even those hoping Korra would Avatar Smash her felt sorry for such a horrible fate.
* General Shiva in ''WesternAnimation/ExoSquad''; imprisoned for not slaughtering the Australian Resistance to the last man, he is given a chance to "redeem himself" by retaking Venus, which he knows to be a suicide mission. But, being a good soldier, he gives it a go anyways. When he gets shot down, even the [[ScoutOut Exoscouts]] who find him see it as a tragedy.
* While he has a [[DracoInLeatherPants number of fans who sympathize with him]], Vlad Masters in ''WesternAnimation/DannyPhantom'' remains the overall BigBad and performs his share of MoralEventHorizon acts. Still, his final moments gave him a big [[TheWoobie woobie moment]] when he not only had to deal with the fact that everyone he wanted would not give him their love, but his most hated [[VitriolicBestBuds "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.
* In the ''WesternAnimation/TeenageMutantNinjaTurtles2003'' 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...
* Hun in ''WesternAnimation/TurtlesForever'', after the Turtles finally convince him that The Shredder is going to destroy TheMultiverse. Hun [[FateWorseThanDeath is erased from reality]] right afterwards. The same thing happened to Casey and April; they both get better once reality is restored, Hun was likely brought back too.
-->'''Leonardo:''' You heard the man. Let's go stop the Shredder.
* ''WesternAnimation/{{Wakfu}}'', at the end of the series. [[WoobieDestroyerOfWorlds Poor]] [[PapaWolf Nox]].
-->'''Nox:''' Twenty minutes? All that [[LifeEnergy wakfu]] spent for a jump of twenty minutes in time? Two hundred years of [[TheseAreThingsManWasNotMeantToKnow researching]] and [[HorrorHunger collecting wakfu]] for ''[[AllForNothing twenty miserable minutes?!]]'' '''[[BigNo NOOOOOO!]]'''
** The real kicker is when Yugo chews Nox out for committing so many atrocities in the name of his delusions. [[HeelRealization Finally seeming]] [[MyGodWhatHaveIDone to understand the truth,]] [[FailureIsTheOnlyOption 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.
** Actually, he doesn't die then. Instead, he teleports away and travels to the grave of his beloved family, [[LoveMakesYouEvil whom he wanted to see again so badly that it was the key motivation for everything he'd done,]] and quietly [[DrivenToSuicide kills himself]]. Which is even ''more'' depressing.
** Technically, it's unclear whether he killed himself, or if he simply died because he surrendered the Eliacube to Yugo and couldn't draw on its energy anymore.
* The death of [[EvilTwin Spider]]-[[OmnicidalManiac Carnage]] in ''WesternAnimation/SpiderManTheAnimatedSeries''. He was a demented, AxCrazy loon who was trying to set of an [[ApocalypseHow Omniversal Metaphysical Annihilationapocalypse]], but when he has a HeelRealisation 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 [[DrivenToSuicide suicide seem like a good idea]], ''it's the best option that there is''.
* ''WesternAnimation/TransformersPrime''.
** 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.
* ''WesternAnimation/TronUprising'': 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 [[NobleTopEnforcer 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.
* ''WesternAnimation/{{Archer}}''
** Major Jakov. The sheer brutality with which Barry usurps and then murders him makes his death a genuine TearJerker, both for the audience and InUniverse.
** 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.
* It's ''very'' hard not to feel sorry for the VillainProtagonist of the ''WesternAnimation/SamuraiJack'' episode "The Tale of X9", a robotic assassin, who was one of several murderous robots created by Aku, but was the only one given [[PersonalityChip 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 [[MoralityPet a tiny dog]] named Lulu ([[RunningGag 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 [[IHaveYourWife holding Lulu hostage.]] Jack knows nothing of this, and when X9 launches his attack, [[CurbStompBattle 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. [[TearJerker It's clearly one of the saddest moments of the entire series.]]

%%No real life examples.