* The Once-ler from ''Literature/TheLorax'', whose drive to build his company has destroyed all of the Truffula trees, leaving a dark wasteland.
* The King in Red, from ''Literature/TwoSerpentsRise'', killed and enslaved a pantheon of gods and tore a hole in time and space after his beloved was sacrificed to feed the hungry gods.
* Francis Dolarhyde from ''Literature/RedDragon''. Sure, he murders whole families and rapes their corpses, but good ''lord'', he had an awful childhood. It gets to the point where you want him to be caught, but you still kinda hope he gets out of the whole mess all right. It helps that Dolarhyde's character development throughout the novel is basically him FightingFromTheInside to prevent a SplitPersonalityTakeover, motivated by ThePowerOfLove. That's enough to make anyone sympathetic.
** [[DepravedBisexual Jame]] [[PsychopathicManchild Gumb]] is implied to be one. Hannibal himself states "Buffalo Bill wasn't born a criminal; he was made one by years of systematic abuse."
** [[MagnificentBastard Hannibal]] himself is definitely one. His idyllic life was shattered when his parents were murdered and he and his little sister were abducted by German deserters who ate his sister and fed him some of her in a broth. No wonder he's AxeCrazy.
* The title character from the Balzac classic ''Literature/CousinBette'' could easily been seen as a female analogue to Heathcliff: childhood abuse, poverty and abandonment by the one man she ever loved (who probably [[AllLoveIsUnrequited never returned her feelings to begin with]]) drove her to a monomaniacal obsession with revenge, from which no-one in her path is safe.
* Ineluki the Storm King, the BigBad of TadWilliams' ''MemorySorrowAndThorn''. It is said that he was the brightest light the [[TheFairFolk Sithi]] had ever known and, had things been different, he might have led them out of their exile and into a new golden age. Instead, he went [[TheseAreThingsManWasNotMeantToKnow down dark paths]], sacrificing [[SelfMadeOrphan his family]], [[JumpingOffTheSlipperySlope his soul]], and ultimately, [[DangerousForbiddenTechnique his life]] to defend his people against the depredations of [[HumansAreBastards humanity]]. Even after death, his hatred sustained him, turning him into a [[TheUndead dark spirit]] that seeks now to return ''everything'' to Unbeing in revenge for his suffering. In the end, this turns out to be the key to his defeat.
* FrankensteinsMonster (in [[Literature/{{Frankenstein}} the original novel]], that is). All of his rage against man, and against Victor Frankenstein in particular, would be gone if just 'one person bothered to look past his macabre appearance and associate with him. But HumansAreBastards, [[DownerEnding so]]... F[[Film/MaryShelleysFrankenstein The 1994 movie]] based on the novel ''did'' manage to get that part right, with the motivations of the monster laid bare.
* Gollum in ''Literature/TheLordOfTheRings''. After centuries of misery and torment, he nearly destroys the quest (dooming Middle Earth to tyranny) because of a HeelFaceDoorSlam. Ironically, [[BreakTheCutie Frodo]] [[spoiler:knowingly claims the ring after suffering months of psychological torment because of it]]. Fortunately, [[DramaticIrony the quest would have failed]] without his [[ProphecyTwist attempt to prevent it]]. Bilbo, Frodo, and Sam taking pity on Gollum was [[BecauseDestinySaysSo necessary]] for the Ring's destruction; and expressly choosing ''not'' to attack and kill him on four separate occasions, even on the slopes of Mount Doom...
-->'''Frodo:''' But do you remember Gandalf's words: "Even Gollum may have something yet to do?" But for him, Sam, I could not have destroyed the Ring. The Quest would have been in vain, even at the bitter end. ''So let us forgive him!'' For the Quest is achieved and now all is over. I am glad you are here with me. Here at the end of all things, Sam.
** Much less so in [[Film/LordOfTheRings the films]], [[AlternativeCharacterInterpretation which rearrange Gollum's character arc]] significantly, making him more of a JerkassWoobie. They made him much more of a {{Woobie}} in the second film and much less in the third, in order to "provide an antagonist for Frodo and Sam". This caused confusion for some viewers, wondering why anyone [[LostAesop "feels sorry for"]] Gollum... [[WordOfGod According to Tolkien]], had Gollum remained loyal to Frodo in the book, he would have taken the Ring and thrown ''himself'' in the fire.
* [[TheDragon Galadan Wolflord]] from ''Literature/TheFionavarTapestry'' turned rather genocidal towards mortals after one stole his girlfriend - but when said mortal wound up getting her killed, he went crazy and decided that the only way to end his pain was to destroy the universe. The only time in the trilogy he shows genuine emotion is when he finds some of the heroes apparently "desecrating" his shrine to her, [[spoiler:and at the very end, when the heroes spare him and he realizes that there is some good in the world - and in himself.]]
* ''Literature/{{Dragonlance}}'': Raistlin Majere has a life that progressively increases in Suck, until he decides that he's going to take vengeance by becoming a '''[[AGodAmI GOD]]'''. And he does it, too. [[spoiler:After he finds out that his godhood will destroy all of creation, leaving only himself in an empty universe, he...does exactly the same thing.]]
** More specifically, that was an alternate-future Raistlin who was insane at that point. When main-timeline Raistlin realizes the consequences of his actions, he ''does'' repent and sacrifices himself to save both the world and (to him, more importantly) his own soul.
** Raistlin is an ambiguous case, however, because his loneliness and isolation are sometimes (or entirely, DependingOnTheWriter) his own fault. Throughout his life, he was offered love and friendship by several people, but [[JerkassWoobie he drove them away with his own pride and bitterness]].
* In ''Literature/MalazanBookOfTheFallen'' by Steven Erikson, the Crippled God is in constant pain after being forcibly summoned and having subsequently crashed into the planet like a meteor. The Crippled God now tries to share his pain with everyone else. Several characters have speculated on whether or not his followers' twisted faith won't let him heal or is it that his pain twists the followers' minds [[WithGreatPowerComesGreatInsanity (even more)]]. He's also poisoning the goddess of the Earth, pushing him into full on OmnicidalManiac territory, as he spreads chaos and death across the known world.
** Also Korabas, the [[spoiler:[[WalkingWasteland Otataral]] [[InstantDeathRadius Dragon]]]]
* In Creator/AlanDeanFoster[='=]s ''HumanxCommonwealth'' series, Flinx's "sister" Mahnahmi is given this treatment in a big way. Considering how messed up she is and what she's suffered in her life, it's hardly surprising that she's become nihilistic, but for some reason, she insists on taking Flinx and everything he loves with her, even while he's busy saving the galaxy.
* The Lazar from ''Literature/TheDeathGateCycle'' have this as their [[PlanetOfHats hat]] - they are undead beings caught forever in a state of hellish agony between life and death, and the only way they can have any release at all is by delivering others into the same torment. The only real exceptions are Jonathon (who's a straight {{Woobie}} mixed with MessianicArchetype) and, ironically, Kleitus, leader of most of the Lazar. He was enough of a MagnificentBastard in life to keep his head following reanimation (though, admittedly, he's a bit more AxCrazy now), and plans to use the other Lazar as his tools to purge the universe of sentient life, so he'll be left ruling an empire of the dead.
* The Chandrian, specifically [[FallenHero Lanre]], in ''TheNameOfTheWind''; Lanre went insane when his love died, and, in the unsuccessful attempt to bring her back, made himself immortal. With suicide now not an option, he decided to kill the rest of the world instead. He's definitely sympathetic in the BackStory, the only question is if he can maintain it as [[ShroudedInMyth Haliax]] in the modern era.
* In Richard Tierney's CthulhuMythos novel ''The Drums of Chaos'', ''Jesus'' is a WoobieDestroyerOfWorlds. His sacrificial death on the cross is intended to open a gateway for the Great Old Ones to come to destroy the world and end everyone's suffering. One of the two heroes of the novel, John Taggart, also used to be a WoobieDestroyerOfWorlds, but changed his mind. Since the world of the CthulhuMythos is a CrapsackWorld, especially in Tierney's version, where it crosses over with George Orwell's Literature/NineteenEightyFour, it is not clear who is in the right, so it is very much an example of GreyAndGrayMorality.
* While most of the villains in ''SwordOfTruth'' are {{Omnicidal Maniac}}s, Nicci is more of this trope. The sixth book, ''Faith of the Fallen'', is mostly devoted to showcasing her mindset and point of view.
* Inverted (and literal) in ''Literature/DeathStar'' with Tenn Graneet, the station's chief gunner. Rather than someone who commits evil acts because of his painful past, he is a somewhat naive JustFollowingOrders commander who believed that the Empire would never fire the Death Star at full power at an inhabited planet. When he realizes that [[StarWarsANewHope they would]] and he carried out that order, he becomes so full of self-loathing that you start to really pity him. Eventually, during the Rebel attack at Yavin, he stalls for a few critical seconds, allowing Luke to blow up the Death Star before the Death Star could blow up Yavin IV.
** Qwi Xux, one of the chief engineers for the Death Star's superlasers, and the creator of the Sun Crusher: she was taken from her village as a little girl and placed in a high-risks and genuinely horrific mathematics/science course with other students, where their lives depended on whether they got the answers right or wrong, and those of their village (if one of the students gets even one answer wrong, the student in question will be forced to watch as their home village is blown away via aerial bombardment and executed shortly thereafter). She was the sole graduate, and the sole survivor of that course, which was also headed by Imperial Grand Moff Wilhuff Tarkin, and it was because of this that she felt driven, to the extent of borderline psychotic obsession, to solve any problem whenever the Empire declares that it wants a solution, often feeling not responsible if it turned out to be a failure in faux-naivete.
** There's also the Grand Admiral Osvald Teshik. Because of a failure in regards to rescuing Coh Veshiv from the Rebel privateer ''Far Orbit'', or any reason to begin with, as he implies that Palpatine did this to him for absolutely no reason whatsoever, he ends up being nearly killed in a battle that Palpatine ensured that he would not win, and that he turned into a cyborg with 3/4s of his body removed, and the near-death experience, and the abuse by various Imperial personnel for his cyborg status, left him extremely cold and nihilistic up until he was saved by a construction worker, and he ends up explaining the battle to the Rebels and the impact it had when he is to be executed for war crimes, having been resigned to his fate, before emitting a mechanical, almost pitiful laugh upon his death.
* Several in MercedesLackey's ''HeraldsOfValdemar'' series, including Tylendel and Lavan Firestorm. Vanyel and Talia both come very close to this trope, but are saved by the support of their friends, Companions, and MindlinkMates.
* Isabella Sordeno from Mindy Mackay's ''Literature/{{Peacebreakers}}'' seems to fit the bill. After being manipulated, abused, and [[spoiler:operated on while conscious]], she snaps and loses her mind, developing into a strategic mastermind and almost singlehandedly [[spoiler:conquers a country]] while exploiting and manipulating everyone around her ForTheEvulz. Eventually, as her malevolence snowballs, her reckless strike against an old enemy ends up [[ZombieApocalypse breaking the world]].
* Trashcan Man in ''TheStand'' plays a role quite similar to Gollum in ''Literature/TheLordOfTheRings'', which makes sense, seeing how the latter was a big inspiration for the former. He actually destroys [[spoiler:the entire [[{{Mordor}} Evil Realm of Las Vegas, turning nearby states into radiation zones]]]] to prove his loyalty to Flagg by bringing him [[spoiler:[[DeusExNukina the Big Fire]]]] to destroy the people of Boulder. This only occurs because Flagg promised him protection from the voices in his head of the people in his hometown who used to tease him for his insanity and {{pyromania|c}}. When one of Flagg's minions use the same language to insult Trash, he snaps and [[spoiler:blows up an airfield, and flees into the desert with a price on his head.]]
** Funny thing, the other guy wasn't even insulting him, he was only making a rude joke of sorts and involuntarily triggered his BerserkButton.
* Luke from ''Literature/PercyJacksonAndTheOlympians'' to the point when even the victims of his nefarious acts (Silena, Thalia, Annabeth) show compassion for him and want to help him. Even Percy, who out right ''resents'' him feels bad for the guy in the end.
** Bessie the Ophiotaurus, from the same series, is an unusual variant on this trope. Whoever kills Bessie and sacrifices her entrails to fire will gain the power to destroy the gods and annihilate human civilization.
* Dear god, Aeglyss, the halfbreed from ''Literature/TheGodlessWorldTrilogy''. After a lifetime of ostracisation and failed attempts at social interaction, he's so damaged that his very presence is contaminating the planet and poisoning the [[TheLifestream Shared]]. By the end, he's diseased, physically ruined, and ready to die, and tries to take the world that's rejected him along for the ride. It's not even deliberate: after failing to enslave the world, he just doesn't care enough about it to try and stop the destruction he's begun.
* [[Literature/{{Wicked}} Elphaba]]. Yes, she went completely mental towards the end. But oh God, [[TearJerker when you read about]] [[FantasticRacism her life...]]
* {{Carrie}} from the book of the same name by Stephen King. She was the ButtMonkey for her entire school life, and at home, her mother beat her, verbally abused her, and locked her in a small closet for up to a day at a time. And she weathered all of it. When she found out that she had telekinetic powers, she exercised them to make them stronger, but not to get revenge. She never even contemplates revenge. But finally, one last, cruel prank goes too far, and the poor girl snaps, taking out of all of her pain and misery on the town around her.
* Literature/{{Cujo}}, again from the book of the same name by Creator/StephenKing, reaches far into the stratosphere of Woobieness. King himself lays it out better than anyone else could:
--> It would perhaps not be amiss to point out that he had always tried to be a good dog. He had tried to do all the things his MAN and his WOMAN, and most of all his BOY, had asked or expected of him. He would have died for them, if that had been required. He had never wanted to kill anybody. He had been struck by something, possibly destiny, or fate, or only a degenerative nerve disease called rabies. Free will was not a factor.
* ''Q Squared'', the Star Trek Novel by ''PeterDavid'', features Jack Crusher in an alternate reality, a good but unhappy man who is targeted by the godlike Trelane, who drives Jack [[spoiler:murderously...and suicidally...insane]]
* Persephone in ''Literature/{{Ravirn}}'' releases the [[spoiler:Necessity virus]] that would have destroyed the entire multiverse without Ravirn's intervention in hopes of breaking Hades' hold on her. It's later implied that she would have done the same again when Hades [[spoiler:is one of the few candidates to replace Necessity and gain absolute power]], except that she trusted Ravirn to stop him instead.
* The Bane (real name Pearlpelt) from ''TheUnderlandChronicles.'' His father killed his other children so Pearlpelt could have more milk and grow stronger. His parents killed each other in a fight, and he saw his mother lying dead with her innards spilled over the ground. To make matters worse, almost all the humans shun him because he's the Bane, and many of his fellow [[YouDirtyRat rats]] honor him and want him to be their king. Eventually, he goes completely off the deep end, becoming an EvilAlbino and a great [[ANaziByAnyOtherName Hitler allegory.]]
* Ari from the ''Literature/MaximumRide'' series. He was born a sweet, innocent child, but he grew up in the shadow of [[spoiler:[[LukeIAmYourFather his half-sister]]]], Max. He was turned into a WolfMan by scientists, and was subject to constant genetic enhancements afterward, eventually becoming a hideous freak. [[spoiler:In the end, though, he gets a HeelFaceTurn--but [[RedemptionEqualsDeath too late]]]].
* Ghwerig the troll from ''TheElenium''. In reality, he is maddened by the loss of Bhelliom and devotes most of the rest of his life to searching for it, and though he eventually finds it, he is killed by [[TheHero Sparhawk]] and Kurik.
* Doesn't seem like it at first, but [[MagnificentBastard Petyr Baelish]] from ''ASongOfIceAndFire''. He was born as one of the poorest nobles, if not ''the'' poorest noble, in the realm, then separated from his family at a young age to live with another family in much, much better standing--throwing in his face what he will never have. He's small, weak, and looked down on by everybody. Nobody even calls him by his real name. Then, [[FromBadToWorse just to make things worse]], he falls in love with one of the daughters, who he isn't allowed to marry because of his birth. He nearly gets himself killed fighting for her and, after he loses, she completely ignores him. Hard not to feel sorry for him...until he becomes a puppeteer in the royal court, [[spoiler:ruins his first love's family and [[ReplacementGoldfish kidnaps her teenage daughter]], kills people off at his convenience, and starts a frickin' civil war]].
** Catelyn Tully, who [[spoiler:turns into a homicidal, undead, noose-happy outlaw leader after witnessing the brutal massacre of her son, herself and companions at a wedding feast, having already lost her husband and her other four children]].
* [[Literature/HarryPotter Barty Crouch Jr.]]. He's a WellDoneSonGuy with a father who never cared about him whatsoever (until Barty Sr. briefly reveals in a moment of clarity that he ''did'' care, and regretted not showing it), who loved his wife and [[WhenYouComingHomeDad work]] far, far more than his own son. He's also incredibly brilliant, one of the few characters to get twelve Outstanding [=OWLs=] in the series (not even ''Hermione'' got twelve Outstandings), probably got all Outstandings on his [=NEWTs=], too, possibly just to please his father. After failing to receive the love and approval of his father, he joined the very faction his father despised, finding approval and a father-figure in Voldemort. Crouch was then sent to prison with little consideration by his father, who proclaimed that he [[IHaveNoSon had no son]]. He's well aware that his father saved him from Azkaban and eternal MindRape via Dementors because his mother begged him to save their son. She herself was dying. The only parent who loved him gave up her life for him and died, and by this point, Crouch was already halfway to madness. It's strongly implied that being under the Imperius Curse for too long has the same effect as MindRape, and he was under one for thirteen solid years thanks to his own unloving father. It's no wonder he stayed very loyal to Voldemort and helped with his ploy to get Harry killed and killed his own father.
** You know what makes it worse? He ultimately receives a FateWorseThanDeath.
** Also, Merope. What she did to Tom Riddle Sr. was absolutely disgusting, but she was abused through most of her life by her father and brother, who were the wizard equivalent of white trash.
* Dark magic caused [[spoiler:Shruikan]] from the ''Literature/InheritanceCycle'' to go batshit insane and becomea tortured OmnicidalManiac. Also, arguably, Galbatorix, who was driven insane by the death of his first dragon.
* Maud in Creator/CatherynneMValente's ''[[Literature/TheGirlWhoCircumnavigatedFairylandInAShipOfHerOwnMaking The Girl Who Circumnavigated Fairyland in a Ship of Her Own Making]]'', whose life as a hero and a great queen in Fairyland was cut short when she was sent back to the real world and her abusive family, so she sought revenge after being pulled back to Fairyland by her friend.
* The eponymous character of ''Literature/SkulduggeryPleasant'' was this after his family was killed. The books always implied that he went a bit off the rails, but in ''Death Bringer'', we find out that it went [[OmnicidalManiac a tad further]] than just UnstoppableRage. [[spoiler:He's Lord Vile.]]
* The novelization for Disney's ''Disney/SnowWhiteAndTheSevenDwarfs'' paints Queen Grimhilde as an extremely dark WoobieDestroyerOfWorlds. For starters, the novel gives her the FreudianExcuse that she was emotionally abused by her [[AbusiveParents father]], a mirror maker, who refused to acknowledge that she was beautiful since she was a child, leading her to be insecure in regards to her beauty. When she did marry Snow White's father, the king, she actually did genuinely care for Snow White as if she were her own daughter. Unfortunately, her father's witch cousins ended up giving her a gift (the magic mirror) that also housed her father's spirit, and it is heavily implied that it was thanks to her father's haunting influence that she started to go insane by the movie.
* Ender in EndersGame is a great [[spoiler:and very literal]] example.
* [[Literature/TheElricSaga Elric of Melniboné]] just can't get a break. Every time he kills it makes him stronger and it also makes him hate himself more. On top of that every girl he loves (each of whom wants to wrap him in the proverbial blanket and feed him the proverbial soup) dies, which usually leads to him needing to wreak revenge on someone. And kill them with his sword and take their soul, and then hate himself. It's a vicious woobie cycle.
* ''InDeath'' series: ''Holiday In Death'' and ''Portrait In Death'' have killers who could be considered this. Those killers suffered losses that was the end of the world for them. They turned to murder because for them, it's the only way to unleash the pain. Those killers are also implied to have been born with untreated mental disorders. Perhaps they are unsympathetic, but it can be agreed that they are pathetic.
* Literature/{{Nibelungenlied}}: By the beginning of the first part, Kriemhild is a tender and meek Princess Classic. By the end of the second part, she is a merciless angel of vengeance who has sacrificed thousands of lives, extirpated her own clan, ruined a kingdom and heavily decimated another in her quest for justice.
* Most of the characters who play in "Literature/BattleRoyale", particularly [[spoiler: Yuko]].
* Brittney Donegal from the ''Literature/{{GONE}}'' series plays a prominent role in the attempts to wipe out the entire population of Perdido Beach with giant man-eating bugs (PLAGUE). But even though she's persists in helping the ongoing genocide attempts by her master, even Sam the hero and big good is reluctant to try and stop her, actually ''apoligising'' for ruining her evil plans.
** Brittney has been enslaved, tortured numerous times in horrific ways, disfigured, has her only family killed and spends three months in a grave in the duration of the series. She's only in four books and Isn't even a significant character in two of them. Can you really hate her in spite of the genocide attempts and destruction she caused?
* In ''A Kiss in Time'', it turns out that the evil witch who cursed Talia and wants to kill her [[spoiler:actually used to be a kindly fairy who helped the royal family. She'd been in charge of watching Talia's older brother (then an infant) while he slept, and noticed too late that he suddenly stopped breathing. She tried unsuccessfully to revive the baby using her magic, only for the child's nanny to walk in and declare that she cursed the boy to die. She was then exiled and reviled as an evil witch.]]
* Exploited in Robert Jordan's ''Literature/{{Wheel of Time}}''. It is revealed in the twelfth book that the Dark One's plan is to force Rand al'Thor to become this. It nearly succeeds, until Rand is saved by the mad voices in his head.
* In one DinoBuzatti short story, ''The Poor Little Boy'', we are told the typical day of Dolfi, a sickly small dark-haired 5 years old boy who always get bullied around by his healthier, blonde classmates. This day, he shows up at the park with a brand new pop gun and -for once- they let him play war with them... Only to play a cruel prank on him, beat him, and break his toy. And to make things worst, he gets yelled at by his mother because he got his clothes dirty. As a friend of his mother concludes : ''Oh! These children! They make a big deal out of everything! Said the other lady annoyed to seem them leave. Well, goodbye then, [[spoiler:Mrs. Hitler!]]''
* Tabaea in ''[[Series/TheLegendsOfEthshar The Spell of the Black Dagger]]'' really only wanted love and acceptance. If her stepfather had managed to sober up long enough to set her up with an apprenticeship, she would have had a perfectly happy life as an honest, law-abiding citizen. She never even thought about killing anyone until she had magically absorbed the predatory instincts of several predatory animals, and she only decided to lead an uprising and take over the city because it was the only way to avoid being arrested for murder. In the end, she died trying to save her city and the world, and her archenemies referred to her, wholly unironically, as "poor little Tabaea."
* A central theme in ''TheLeftHandOfGod'' trilogy is Redeemer Bosco trying to invoke this trope in Thomas Cale -- taking him in to be raised in the harsh, abusive environment of the Sanctuary of the Redeemers while giving him TrainingFromHell to prepare him, then, when he's escaped and captured again, ensuring he sees himself betrayed by the one he loves and has his view of humanity crushed -- because he believes Cale to be the Angel of Death, sent by {{God}} to wipe out humanity for its sins.
* Finneus from ''Literature/ChameleonMoon'' is one of these. [[spoiler: If he feels any negative emotion whatsoever, he creates explosions. Forcing himself to be happy all the time has put him in a permanent state of shell shock.]]
* Ronald Waldstein from ''Literature/TimeRiders''. His wife, Eleanor, and son, Gabriel, both died. [[spoiler:Literally wanting to see the world ruined is still nowhere near justified, but he implied to be acting on something else too.]]
* [[spoiler: Amy Dunne]] in ''Literature/GoneGirl''. Though we don't see it firsthand, there is heavy implication that [[spoiler: she's been psychologically abused all her life by her parents, who created the fictional character of 'Amazing Amy' who always did everything right and who the real Amy never had a hope of living up to.]]