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* ''LightNovel/TheGardenOfSinners'': ''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.
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* ''LightNovel/TheGardenOfSinners'': ''Overlooking View'' has [[IllGirl [[DelicateAndSickly 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.
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cleaning up Pyrrhic Villainy misuse and wicks per TRS
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* This is ultimately how ''Literature/ASeriesOfUnfortunateEvents'' ends, when [[BigBad Count Olaf]] is ImpaledWithExtremePrejudice by a harpoon gun by [[JerkAss Ishmael]]. By this point he has lost: his true love, friends, co-workers, parents, and [[PyrrhicVillainy his last chance at obtaining the Baudelaire fortune]]
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* This is ultimately how ''Literature/ASeriesOfUnfortunateEvents'' ends, when [[BigBad Count Olaf]] is ImpaledWithExtremePrejudice by a harpoon gun by [[JerkAss Ishmael]]. By this point he has lost: his true love, friends, co-workers, parents, and [[PyrrhicVillainy his last chance at obtaining the Baudelaire fortune]]fortune.
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removed Up To Eleven wicks
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*** Turned UpToEleven in ''Belgarath The Sorceror'' when Belgarath as narrator almost casually notes that ''Zedar was always afraid of the dark''.
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*** Turned UpToEleven in In ''Belgarath The Sorceror'' when Sorceror'', Belgarath as narrator almost casually notes that ''Zedar was always afraid of the dark''.
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* In ''Literature/SpaceGlass'', Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.
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* In ''Literature/SpaceGlass'', Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.moments.
* ''Literature/BazilBroketail'': Smilgax, in Bazil's eyes at least. The eponymous hero, [[TurnTheOtherCheek despite being bullied and even mutilated by Smilgax]], takes pity on him because he was apparently brainwashed since childhood and thus given no choice in his life but to turn evil.
* ''Literature/BazilBroketail'': Smilgax, in Bazil's eyes at least. The eponymous hero, [[TurnTheOtherCheek despite being bullied and even mutilated by Smilgax]], takes pity on him because he was apparently brainwashed since childhood and thus given no choice in his life but to turn evil.
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** Gellert Grindelwald's death at Voldemort's hand is also portrayed with sympathy. At that point, he'd been locked in the prison he built for over half a century with nothing to do but wallow over his own misdeeds and the only person he'd ever cared about had been dead for almost a year.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him while he's brainwashed to be her mindless slave, but her whole life, which involved her being a victim of constant abuse from his [[AbusiveParent father]] and [[BigBrotherBully brother]] and ended with her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him while he's brainwashed to be her mindless slave, but her whole life, which involved her being a victim of constant abuse from his her [[AbusiveParent father]] and [[BigBrotherBully brother]] and ended with her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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Captain Scratch is a murderous {{Jerkass}} who WouldHurtAChild, but Oliver feels a bit of pity for him after the crew tricks Scratch into thinking that he's been killed and come back as a ghost who's been BarredFromTheAfterlife, and then leaves him marooned.
--> ''Captain Scratch grew smaller and smaller. Even though no one had shed a tear for him he gave us a last forlorn wave of his hand. Despite myself, I waved back.''
--> ''Captain Scratch grew smaller and smaller. Even though no one had shed a tear for him he gave us a last forlorn wave of his hand. Despite myself, I waved back.''
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** One of the primary themes surrounding [[Characters/HarryPotterLordVoldemort Voldemort's (a.k.a. Tom Riddle's)]] character. For all his abominable crimes, his lack of remorse over them, and his megalomania; his lifelong fundamental inability to appreciate any form of human contact (a trait unique to him among the series' cast) which has fuelled his evil life ultimately make him a creature who is pitied by his [[ArchEnemy Arch-Enemies]]. Harry even encourages him to be a human being and try and save himself from the awful fate that awaits him if he doesn't mend his mangled soul, before the duel that results in Voldemort's death.
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** Gollum is presented throughout as a TragicVillain and a generally pitiable figure -- it's also very hard not to feel sorry for him when he falls into the Fires of Doom with his "precious."
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* ''Literature/SpaceGlass'' Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.
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* ''Literature/SpaceGlass'' In ''Literature/SpaceGlass'', Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.
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* The titular [[OurGhoulsAreCreepier Ghoul]] of {{Literature/Amina}} (Creator/EdwardLucasWhite, 1906) is a literal [[ImAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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* The titular [[OurGhoulsAreCreepier Ghoul]] of {{Literature/Amina}} (Creator/EdwardLucasWhite, 1906) is a literal [[ImAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.children.
* ''Literature/SpaceGlass'' Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.
* ''Literature/SpaceGlass'' Bagok, Reeva, and the Marauder all had miserable lives, and they, with Marvelous help, were only trying to escape it. Marvelous recollects all of their pain during his final moments.
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dewicking Famous Last Words per TRS
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** [[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--[[Literature/XWingSeries 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.
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** [[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--[[Literature/XWingSeries 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.
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* ''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.
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* ''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, last words, wherein he refuses to pray and asks only that he buried by his son, are quite touching.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him while he's too intoxicated to decide for himself, but her whole life, which involved mostly with her being a victim of constant abuse from his [[AbusiveParent father]] and [[BigBrotherBully brother]] and ended with her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him while he's too intoxicated brainwashed to decide for himself, be her mindless slave, but her whole life, which involved mostly with her being a victim of constant abuse from his [[AbusiveParent father]] and [[BigBrotherBully brother]] and ended with her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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Let's be real here, we never learn what Barty Crouch Jr. wanted and if it was just a father figure or shared the Dark Lord's ideals which made him the ideal father. Admittedly, Harry is described as feeling a momentary gut-punch when he hears of Junior's ultimate fate but that's it and it is implied that he was merely disturbed by such a thing happening rather than feeling sympathetic towards the individual in any way. So not it wasn't played for tragedy in-universe. And as for nit-picking he didn't even die exactly
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** [[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 going too far]], but also very sad, considering how neglected he was by his own father.
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Let's be real here, Barty Crouch Jr.
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Durza doesn't really qualify because he is simply a different person from the unhappy Carsaib. Carsaib died the moment that the demon Durza took over and he of course had no emotional turmoil over his victim's life
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* 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.
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It is not enough for the death to be horrible, it is not enough that some may find it too much and it is not enough that one can't find it satisfying. Its all about the death being played for tragedy and there are neither characters around to treat it as something sad nor does the narration give any indication that it is meant to be a source of sadness. So no, no alas poor Patrick here
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* 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.
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* ''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.
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* ''LightNovel/KaraNoKyoukai'': ''LightNovel/TheGardenOfSinners'': ''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.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him once he's too intoxicated to decide for himself, but her whole life, which leads to her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him once while he's too intoxicated to decide for himself, but her whole life, which leads to involved mostly with her being a victim of constant abuse from his [[AbusiveParent father]] and [[BigBrotherBully brother]] and ended with her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
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** Merope Gaunt [[SlippingAMickey drugged]] [[StalkerWithACrush a Muggle man she pined for]], despite said Muggle man already being romantically involved with another woman, as well as having a [[ChildByRape son]] with him once he's too intoxicated to decide for himself, but her whole life, which leads to her [[DeathByChildbirth dying shortly after her son's birth]], is nothing but a series of TraumaCongaLine. Harry is dismissive of her [[DespairEventHorizon inability to go on living after the man she pined for left her]], but Dumbledore has pity for her.
-->'''Dumbledore:''' Merope Riddle chose death in spite of a son who needed her, but do not judge her too harshly, Harry. She was greatly weakened by long suffering and she never had your mother's courage.
-->'''Dumbledore:''' Merope Riddle chose death in spite of a son who needed her, but do not judge her too harshly, Harry. She was greatly weakened by long suffering and she never had your mother's courage.
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* ''Literature/TheDaVinciCode'': has Silas who spent all his life being treated as a monster and an outcast for being an albino, so much that the one time that someone showed kindness to him, he ended up joining his religious crusade out of gratefulness. While this led him to commit terrible crimes, by the end he went through a big MyGodWhatHaveIDone moment where he prayed not for his life but for his adopted father's and died hoping to find piece and God's forgiveness in the end.
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* ''Literature/TheDaVinciCode'': has Silas who spent all his life being treated as a monster and an outcast for being an albino, so much that the one time that someone showed kindness to him, he ended up joining his religious crusade out of gratefulness. While this led him to commit terrible crimes, by the end he went through a big MyGodWhatHaveIDone moment where he prayed not for his life but for his adopted father's and died hoping to find piece peace and God's forgiveness in the end.
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an abusive man who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he's being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who UsedToBeASweetKid seeking a better life by running away from his abusive family, only to end up as a villain who [[BecameTheirOwnAntithesis became just like the people he tried to escape from]].
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' ''WesternAnimation/{{Frozen|2013}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an abusive man who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he's being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who UsedToBeASweetKid seeking a better life by running away from his abusive family, only to end up as a villain who [[BecameTheirOwnAntithesis became just like the people he tried to escape from]].
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* The titular [[OurGhoulsAreCreepier Ghoul]] of Literature/Amina (1906) is a literal [[ImAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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* The titular [[OurGhoulsAreCreepier Ghoul]] of Literature/Amina (1906) {{Literature/Amina}} (Creator/EdwardLucasWhite, 1906) is a literal [[ImAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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* The titular [[OurGhoulsAreCreepier Ghoul]] of "Literature/Amina" is a literal [[I'mAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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* The titular [[OurGhoulsAreCreepier Ghoul]] of "Literature/Amina" Literature/Amina (1906) is a literal [[I'mAHumanitarian [[ImAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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* The BigBad of the third ''Literature/AlexRider'' book, General Sarov, is only doing what he does [[WellIntentionedExtremist out of a misguided belief that he is doing what is right for his country]], and greatly admires Alex because, even though he is trying to stop his plan, he is also doing what he believes is right. Indeed, he plans to adopt Alex and raise him as his own son. When Alex rejects him and tells him he'd rather be dead than have a father like him, Sarov is DrivenToSuicide. This trope is implied in the book, where his death happens offscreen, but it is more apparent in the graphic novel adaptation, where Sarov is visibly distressed by Alex's rejection and sheds a tear as he puts the gun to his head.
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* The BigBad of the third ''Literature/AlexRider'' book, General Sarov, is only doing what he does [[WellIntentionedExtremist out of a misguided belief that he is doing what is right for his country]], and greatly admires Alex because, even though he is trying to stop his plan, he is also doing what he believes is right. Indeed, he plans to adopt Alex and raise him as his own son. When Alex rejects him and tells him he'd rather be dead than have a father like him, Sarov is DrivenToSuicide. This trope is implied in the book, where his death happens offscreen, but it is more apparent in the graphic novel adaptation, where Sarov is visibly distressed by Alex's rejection and sheds a tear as he puts the gun to his head.head.
* The titular [[OurGhoulsAreCreepier Ghoul]] of "Literature/Amina" is a literal [[I'mAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
* The titular [[OurGhoulsAreCreepier Ghoul]] of "Literature/Amina" is a literal [[I'mAHumanitarian man-eating]] HumanoidAbomination. She's hostile to Waldo, and humans in general, but she is a proud creature of her own [[HumanSubspecies kind]], and her main goal appears to be to feed her children. Even though Waldo barely escaped her with his life, he's notably saddened when the Consul and his guards gun down her and her children.
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Changing wick and Cross Wicking second example.
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* 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.
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* In ''Literature/TheDarkTower'' there is Creator/StephenKing's ''Literature/TheDarkTower2004'':
** After Mordred kills Flagg/Walter/Marten, finally eliminating one of King's great villains, the narration briefly runs through Flagg's life. It gives him a FreudianExcuse (he was raped as a teenager) and manages to wring some small amount of sympathy from Flagg's death.
** The death of Trampas, one of the {{Mooks}} guarding theDevar-Toi.Devar-Toi, is rather sad. 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.
** After Mordred kills Flagg/Walter/Marten, finally eliminating one of King's great villains, the narration briefly runs through Flagg's life. It gives him a FreudianExcuse (he was raped as a teenager) and manages to wring some small amount of sympathy from Flagg's death.
** The death of Trampas, one of the {{Mooks}} guarding the
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* ''Literature/DrGretaHelsing'': Leonora van Dorne is an UnwittingPawn who has no idea her [[FountainOfYouth age-reversing magic]] is harming other people and [[ThinDimensionalBarrier destabilizing reality]]. When she learns, she immediately sacrifices her life in an attempt to undo the harm she's caused, even though it's [[SenselessSacrifice too late]] for it to help.
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live a better one]], but ended up as a villain who was willing to [[BecameTheirOwnAntithesis become just like the people he tried to escape]].
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator abusive man who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is he's being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live UsedToBeASweetKid seeking a better one]], but ended life by running away from his abusive family, only to end up as a villain who was willing to [[BecameTheirOwnAntithesis become became just like the people he tried to escape]].escape from]].
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live a better one]], but ended up as a villain who was willing to [[BecameTheirOwnAntithesis become just like the people he tried to escape]].
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* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live a better one]], but ended up as a villain who was willing to [[BecameTheirOwnAntithesis become just like the people he tried to escape]].escape]].
* The BigBad of the third ''Literature/AlexRider'' book, General Sarov, is only doing what he does [[WellIntentionedExtremist out of a misguided belief that he is doing what is right for his country]], and greatly admires Alex because, even though he is trying to stop his plan, he is also doing what he believes is right. Indeed, he plans to adopt Alex and raise him as his own son. When Alex rejects him and tells him he'd rather be dead than have a father like him, Sarov is DrivenToSuicide. This trope is implied in the book, where his death happens offscreen, but it is more apparent in the graphic novel adaptation, where Sarov is visibly distressed by Alex's rejection and sheds a tear as he puts the gun to his head.
* The BigBad of the third ''Literature/AlexRider'' book, General Sarov, is only doing what he does [[WellIntentionedExtremist out of a misguided belief that he is doing what is right for his country]], and greatly admires Alex because, even though he is trying to stop his plan, he is also doing what he believes is right. Indeed, he plans to adopt Alex and raise him as his own son. When Alex rejects him and tells him he'd rather be dead than have a father like him, Sarov is DrivenToSuicide. This trope is implied in the book, where his death happens offscreen, but it is more apparent in the graphic novel adaptation, where Sarov is visibly distressed by Alex's rejection and sheds a tear as he puts the gun to his head.
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* This is ultimately how ''Literature/ASeriesOfUnfortunateEvents'' ends, when [[BigBad Count Olaf]] is ImpaledWithExtremePrejudice by a harpoon gun by [[JerkAss Ishmael]]. By this point he has lost: his true love, friends, co-workers, parents, and [[PyrrhicVillainy his last chance at obtaining the Baudelaire fortune]]
* 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.
* ''Literature/DragonsOfRequiem'':
** Queen Solina from ''Dragonlore''. She spent all of her time slaughtering as many Vir Requis as possible as punishment for the amount of mistreatment she was subjected to by them growing up, not to mention that they killed her parents and banished her. It isn't until the final book where she realizes that she's just a sad woman who was blinded by her hatred, when all she truly wanted was to be with Elethor, her true love. Her final words really hammer it in.
--> '''Solina''': "I'm sorry. I'm sorry for how much I hurt you. All I wanted was to be with you here. I'm sorry."
** Prince Leresy Cadigus from ''The Dragon War'' was a [[ButtMonkey pitiful]] HateSink [[SmugSnake who acted very haughty]] and believed he "deserved" everything he asked for, when he never earned it. He even put Rune and Tilla at risk in a desperate attempt to win his father's love again. When that fails, he lashes out at his father and brutally kills him, thus saving Rune and his sister Kaelyn and ending the trilogy's civil war. [[RedemptionEqualsDeath Shame he took a bullet in the process]].
* ''Literature/HarryPotter''
** Severus Snape. The subsequent chapter reveals that (despite his faults) he's not actually a villain. But Harry and the reader would have still assumed he was at this point, and it's 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 going too far]], but also 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 him to death because of his one moment of mercy for Harry.
* Franchise/StarWarsLegends:
** [[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--[[Literature/XWingSeries 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.
** Though the ''Literature/RevengeOfTheSith'' novelization makes clear that Count Dooku is TheSociopath, you can't help but feel for him when seconds from death, he realizes everything he has done or accomplished, all his talent and power and intellect, has been used by Sidious to fulfill his plans with no regard for Dooku's wishes. Even worse, he realizes Sidious had always planned to kill and replace him. "Treachery is the way of the Sith."
%%* Nearly every book in the ''Literature/{{Redwall}}'' series uses this trope, and half the time, it's the BigBad!
* 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.
*** Turned UpToEleven in ''Belgarath The Sorceror'' when Belgarath as narrator almost casually notes that ''Zedar was always afraid of the dark''.
** 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.
-->Binabik looked at him curiously. “The innocent can be molded, as those children were, but sometimes luck is granting that they can be molded back. I have little belief in evil beyond redeeming, Sludig.”\\
“Oh?” The Rimmersman laughed harshly. “What about your Storm King? What good thing could you possibly say about such a black-hearted hellspawn as that?”\\
“Once he loved his people more than his own life,” Binabik said quietly.
** 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}}'', Creator/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. Him being born disfigured and never being given a chance to live like a normal person, which was what he desired the most, led him to use his charisma and talents for evil because only there did he find acceptance and by the end he died happy that found at least some affection from Christine.
* 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 a FateWorseThanDeath. 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.]]
* Not even an AxCrazy {{Jerkass}} like Cato deserves to be [[spoiler:EatenAlive by Mutts for over ''twenty hours'']] in ''Literature/TheHungerGames''.[[note]]Some sort of body armor that Cato most likely got from the feast earlier kept him from being instantly killed.[[/note]]
%%** The way [[spoiler:Glimmer]] bites it is pretty nasty, especially her cries for help.
* Alfred Builder in ''Literature/ThePillarsOfTheEarth'', in a BigBadWannabe sort of way. He was a [[BigBrotherBully Big (Step)brother Bully]] to Jack and Martha, got Jack kicked off of the building site of Kingsbridge Cathedral, married [[TheWoobie Aliena]] out of spite just so Jack couldn't have her and treated her like crud, [[NoGoodDeedGoesUnpunished betrayed his stepbrother when he had the decency to hire him after all he did]], and even tried to ''[[RapeIsASpecialKindOfEvil friggin' rape Aliena at knifepoint]]''. However, he becomes a lot more sympathetic once you realize that, unlike [[SerialRapist Willaim]] [[DisproportionateRetribution Hamleigh]] or [[SinisterMinister Waleran]] [[AmbitionIsEvil Bigod]], he acted the way he did not because he wanted power or [[ItAmusedMe because he enjoyed it]], but because [[JerkassWoobie his whole adult life he had to deal with one tragedy after another]]: his mother's death, his father favoring his stepson over him, the woman he loved turning down his marriage proposal, and his father's death. Everything he did was out of revenge for the world treating him awfully. Aliena even muses as he lays dying that he could have been a better, happier person had he just been ''nicer:''
-->"She thought, as she looked into his eyes, that he had never been compassionate himself, nor forgiving, nor generous. He had nursed his resentments and hatreds all his life, and had taken his pleasure from acts of malice and revenge. Your life ''could'' have been different, Alfred, she thought. You could have been kind to your sister, and forgiven your stepbrother for being cleverer than you. You could have married for love instead of revenge. You could have been loyal to Prior Philip. You could have been happy."
* ''Literature/TheDaVinciCode'': has Silas who spent all his life being treated as a monster and an outcast for being an albino, so much that the one time that someone showed kindness to him, he ended up joining his religious crusade out of gratefulness. While this led him to commit terrible crimes, by the end he went through a big MyGodWhatHaveIDone moment where he prayed not for his life but for his adopted father's and died hoping to find piece and God's forgiveness in the end.
* ''Literature/{{Renegades}}'': Hawthorne steals medicine and uses it to create deadly drugs, but it's hard not to empathize with her when Frostbite's team "[[DePower neutralizes]]" her and then tortures her to death for their own sick amusement.
* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live a better one]], but ended up as a villain who was willing to [[BecameTheirOwnAntithesis become just like the people he tried to escape]].
* 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.
* ''Literature/DragonsOfRequiem'':
** Queen Solina from ''Dragonlore''. She spent all of her time slaughtering as many Vir Requis as possible as punishment for the amount of mistreatment she was subjected to by them growing up, not to mention that they killed her parents and banished her. It isn't until the final book where she realizes that she's just a sad woman who was blinded by her hatred, when all she truly wanted was to be with Elethor, her true love. Her final words really hammer it in.
--> '''Solina''': "I'm sorry. I'm sorry for how much I hurt you. All I wanted was to be with you here. I'm sorry."
** Prince Leresy Cadigus from ''The Dragon War'' was a [[ButtMonkey pitiful]] HateSink [[SmugSnake who acted very haughty]] and believed he "deserved" everything he asked for, when he never earned it. He even put Rune and Tilla at risk in a desperate attempt to win his father's love again. When that fails, he lashes out at his father and brutally kills him, thus saving Rune and his sister Kaelyn and ending the trilogy's civil war. [[RedemptionEqualsDeath Shame he took a bullet in the process]].
* ''Literature/HarryPotter''
** Severus Snape. The subsequent chapter reveals that (despite his faults) he's not actually a villain. But Harry and the reader would have still assumed he was at this point, and it's 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 going too far]], but also 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 him to death because of his one moment of mercy for Harry.
* Franchise/StarWarsLegends:
** [[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--[[Literature/XWingSeries 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.
** Though the ''Literature/RevengeOfTheSith'' novelization makes clear that Count Dooku is TheSociopath, you can't help but feel for him when seconds from death, he realizes everything he has done or accomplished, all his talent and power and intellect, has been used by Sidious to fulfill his plans with no regard for Dooku's wishes. Even worse, he realizes Sidious had always planned to kill and replace him. "Treachery is the way of the Sith."
%%* Nearly every book in the ''Literature/{{Redwall}}'' series uses this trope, and half the time, it's the BigBad!
* 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.
*** Turned UpToEleven in ''Belgarath The Sorceror'' when Belgarath as narrator almost casually notes that ''Zedar was always afraid of the dark''.
** 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.
-->Binabik looked at him curiously. “The innocent can be molded, as those children were, but sometimes luck is granting that they can be molded back. I have little belief in evil beyond redeeming, Sludig.”\\
“Oh?” The Rimmersman laughed harshly. “What about your Storm King? What good thing could you possibly say about such a black-hearted hellspawn as that?”\\
“Once he loved his people more than his own life,” Binabik said quietly.
** 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}}'', Creator/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. Him being born disfigured and never being given a chance to live like a normal person, which was what he desired the most, led him to use his charisma and talents for evil because only there did he find acceptance and by the end he died happy that found at least some affection from Christine.
* 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 a FateWorseThanDeath. 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.]]
* Not even an AxCrazy {{Jerkass}} like Cato deserves to be [[spoiler:EatenAlive by Mutts for over ''twenty hours'']] in ''Literature/TheHungerGames''.[[note]]Some sort of body armor that Cato most likely got from the feast earlier kept him from being instantly killed.[[/note]]
%%** The way [[spoiler:Glimmer]] bites it is pretty nasty, especially her cries for help.
* Alfred Builder in ''Literature/ThePillarsOfTheEarth'', in a BigBadWannabe sort of way. He was a [[BigBrotherBully Big (Step)brother Bully]] to Jack and Martha, got Jack kicked off of the building site of Kingsbridge Cathedral, married [[TheWoobie Aliena]] out of spite just so Jack couldn't have her and treated her like crud, [[NoGoodDeedGoesUnpunished betrayed his stepbrother when he had the decency to hire him after all he did]], and even tried to ''[[RapeIsASpecialKindOfEvil friggin' rape Aliena at knifepoint]]''. However, he becomes a lot more sympathetic once you realize that, unlike [[SerialRapist Willaim]] [[DisproportionateRetribution Hamleigh]] or [[SinisterMinister Waleran]] [[AmbitionIsEvil Bigod]], he acted the way he did not because he wanted power or [[ItAmusedMe because he enjoyed it]], but because [[JerkassWoobie his whole adult life he had to deal with one tragedy after another]]: his mother's death, his father favoring his stepson over him, the woman he loved turning down his marriage proposal, and his father's death. Everything he did was out of revenge for the world treating him awfully. Aliena even muses as he lays dying that he could have been a better, happier person had he just been ''nicer:''
-->"She thought, as she looked into his eyes, that he had never been compassionate himself, nor forgiving, nor generous. He had nursed his resentments and hatreds all his life, and had taken his pleasure from acts of malice and revenge. Your life ''could'' have been different, Alfred, she thought. You could have been kind to your sister, and forgiven your stepbrother for being cleverer than you. You could have married for love instead of revenge. You could have been loyal to Prior Philip. You could have been happy."
* ''Literature/TheDaVinciCode'': has Silas who spent all his life being treated as a monster and an outcast for being an albino, so much that the one time that someone showed kindness to him, he ended up joining his religious crusade out of gratefulness. While this led him to commit terrible crimes, by the end he went through a big MyGodWhatHaveIDone moment where he prayed not for his life but for his adopted father's and died hoping to find piece and God's forgiveness in the end.
* ''Literature/{{Renegades}}'': Hawthorne steals medicine and uses it to create deadly drugs, but it's hard not to empathize with her when Frostbite's team "[[DePower neutralizes]]" her and then tortures her to death for their own sick amusement.
* [[spoiler:[[TragicVillain Prince Hans]]]] in ''Disney/{{Frozen}}'' does things that are inexcusable, but the retelling ''Literature/AFrozenHeart'' delves more into his DarkAndTroubledPast and his FreudianExcuse. [[spoiler:His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons and allows them to harass and torment their youngest brother. Ironically, Hans let his issues with family and desire to earn [[WellDoneSonGuy his father's respect]] make him do things he initially considered wrong, namely leaving Anna to die and trying to murder Elsa.]] As he is being sent back at the end, it feels a lot less like the triumphant defeat of a villain and more like the tragedy of someone who [[UsedToBeASweetKid started out as a man who wanted to escape his horrible life to live a better one]], but ended up as a villain who was willing to [[BecameTheirOwnAntithesis become just like the people he tried to escape]].
