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* Toki, she started out as this in [[http://akaichounokoe.deviantart.com/gallery/?q=Time+heals+no+wounds#/d4z3yme Time Heals No Wounds II]], before her redemption and change of heart. To further drive the point home, she wasn't always like that and was rather sweet, however, deep within the pain from being abused and then neglected (on top of that almost dying of cancer, after it was allowed to reach later stages) eventually poisoned her, allowing her personality to be tainted and turning her into the mentally ill intimidating wreck that she is, making sure no one could ever hurt her again and that she would be one to hurt, in control, and to be betray, just like it had happened to her. The

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* Toki, she started out as this in [[http://akaichounokoe.deviantart.com/gallery/?q=Time+heals+no+wounds#/d4z3yme Time Heals No Wounds II]], before her redemption and change of heart. To further drive the point home, she wasn't always like that and was rather sweet, however, deep within the pain from being abused and then neglected (on top of that almost dying of cancer, after it was allowed to reach later stages) eventually poisoned her, allowing her personality to be tainted and turning her into the mentally ill intimidating wreck that she is, making sure no one could ever hurt her again and that she would be one to hurt, in control, and to be betray, just like it had happened to her. The quote below is just a summmary:

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* Toki, she started out as this in [[http://akaichounokoe.deviantart.com/gallery/?q=Time+heals+no+wounds#/d4z3yme Time Heals No Wounds I]], before her redemption and change of heart.

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* Toki, she started out as this in [[http://akaichounokoe.deviantart.com/gallery/?q=Time+heals+no+wounds#/d4z3yme Time Heals No Wounds I]], II]], before her redemption and change of heart.heart. To further drive the point home, she wasn't always like that and was rather sweet, however, deep within the pain from being abused and then neglected (on top of that almost dying of cancer, after it was allowed to reach later stages) eventually poisoned her, allowing her personality to be tainted and turning her into the mentally ill intimidating wreck that she is, making sure no one could ever hurt her again and that she would be one to hurt, in control, and to be betray, just like it had happened to her. The
--->'''Brownie''': Toki was once a sweet shy innocent girl who only wanted to be loved, according to Jinx and Spin, but the birth of Frailine turned her shallow, cold, cruel, dominating, calculating, and worst of all, sadistic.
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* From ''WebVideo/UltraFastPony'', Rainbow Dash. She has an obnoxious personality and likes to gloat about breaking other ponies' stuff. ("Like, OMC, I totally wrecked your house, and I'm not even gonna apologize!") She's also an orphan with a HilariouslyAbusiveChildhood, and she wants a real family more than anything else. [[LampshadeHanging Other characters even note]] that they're (briefly) torn over how to feel towards Dash:
-->'''Rainbow Dash''': I just want to be loved for once at the gala.\\
'''The Choir''': No pony likes Rainbow Dash / Because she is annoying / But now I kind of pity her / No wait, the feeling has passed.
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** Zaboo is creepy and horrible with people, yeah, but he doesn't qualify as a JERKASS. Even when he does rude things, it's always done with the best intentions and a loving heart. He's just...super creepy. (And a complete Woobie.)

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** Zaboo is creepy and horrible with people, yeah, but he doesn't qualify as a JERKASS.'''jerkass'''. Even when he does rude things, it's always done with the best intentions and a loving heart. He's just...super creepy. (And a complete Woobie.)
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Removing Nightmare Fuel potholes. NF should be on YMMV only.


* Light in ''[[DNAKpts4tv Death Note: The Abridged Series (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also [[BlackComedyRape being molested by Shinigami]] and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.

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* Light in ''[[DNAKpts4tv Death Note: The Abridged Series (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also [[BlackComedyRape being molested by Shinigami]] and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
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Moving to the Web Animation subpage.


* Natsumi from ''[[http://www.youtube.com/watch?v=Pw4LstqkNcw Natsumi Step!]]'' She a [[TheWoobie Woobie]] for [[spoiler:[[DrivenToSuicide commiting suicide]] and going to {{Hell}}]], and a {{Jerkass}} for [[spoiler:[[MoralEventHorizon murdering her boyfriend]]]].
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* Natsumi from ''[[http://www.youtube.com/watch?v=Pw4LstqkNcw Natsumi Step!]]'' She a [[TheWoobie Woobie]] for [[spoiler:[[DrivenToSuicide commiting suicide]] and going to {{Hell}}]], and a {{Jerkass}} for [[spoiler:[[MoralEventHorizon murdering her boyfriend]]]].
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* Esau from ''{{Fanfic/Stray}}'', who could be described as Adamska's EvilCounterpart. He's a {{Tykebomb}} agent of the Patriots who initially comes across as a SmugSnake and does some rather cruel things in his efforts against the protagonists, but his back story is deeply unhappy. [[spoiler: And in true ''MetalGearSolid'' villain fashion, his death scene is [[AlasPoorVillain played for tragedy.]]]]

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* Esau from ''{{Fanfic/Stray}}'', who could be described as Adamska's EvilCounterpart. He's a {{Tykebomb}} agent of the Patriots who initially comes across as a SmugSnake and does some rather cruel things in his efforts against the protagonists, but his back story is deeply unhappy. [[spoiler: And in true ''MetalGearSolid'' ''Franchise/MetalGear'' villain fashion, his death scene is [[AlasPoorVillain played for tragedy.]]]]

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] could be interpreted as one. Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their [[MarySue only flaw]].

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] could be interpreted as one. one.
**
Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their [[MarySue only flaw]].




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* Tim in ''WebVideo/MarbleHornets'' initially comes across this way. Later on, however, the series makes sure to point out that [[WhatTheHellHero Jay kinda earned the reactions he got]], causing Tim to end up as a straight-up [[TheWoobie vanilla Woobie]] instead.
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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: {[[MindScrew probably]]) [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]

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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: {[[MindScrew ([[MindScrew probably]]) [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]
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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also [[BlackComedyRape being molested by Shinigami]] and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.

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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries The Abridged Series (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also [[BlackComedyRape being molested by Shinigami]] and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.

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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities]] instead of [[AssholeVictim criminals]]) but he's also [[BlackComedyRape being molested by Shinigami Shinigami]] and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe is killing off celebrities instead of criminals) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.

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* Light in ''[[DNAKpts4tv Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe [[TookALevelInJerkass is killing off celebrities celebrities]] instead of criminals) [[AssholeVictim criminals]]) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: {[[MindScrew probably]]} [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]

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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: {[[MindScrew probably]]} probably]]) [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]
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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: [[MindScrew probably]] [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]

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** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: [[MindScrew probably]] {[[MindScrew probably]]} [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]
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* Light in ''[[DNAKpts4tv WebVideo/DeathNoteTheAbridgedSeriesKpts4tv]]''. Sure he's a SerialKiller (who in this universe is killing off celebrities instead of criminals) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.

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* Light in ''[[DNAKpts4tv WebVideo/DeathNoteTheAbridgedSeriesKpts4tv]]''.Death Note: TheAbridgedSeries (Kpts4tv)]]''. Sure he's a SerialKiller (who in this universe is killing off celebrities instead of criminals) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
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* Light in ''[[DNAKpts4tv WebVideo/DeathNoteTheAbridgedSeriesKpts4tv]]''. Sure he's a SerialKiller (who in this universe is killing off celebrities instead of criminals) but he's also being molested by Shinigami and [[HoYay the man he's fallen in love with]] just wants to see him executed. His FreakOut after [[spoiler: L dies]] (while simultaneously being NightmareFuel) cements his [[TheWoobie Woobie]] status.
** Mello is a strong candidate as well. That poor psycho had to grow up with [[JerkAss Near!]] And [[spoiler: [[PoorCommunicationKills he gets killed over a stupid misunderstanding.]]]]
** Poor Mikami. [[CosmicPlaything The writer really has it in for him.]] [[http://www.youtube.com/watch?v=F_QhsRInEbM&feature=channel&list=UL]]
** L is ever a Grade A JerkAss but still being [[spoiler: being BuriedAlive / resurrected just to die again]] was not cool. [[TheReveal Actually that]] was [[spoiler: [[MindScrew probably]] [[SerialKiller Beyond Birthday]] who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as [[SexSlave the real L was being kept alive in Light's basement / lovenest for the last five years.]] ([[MindScrew Probably.]])]]
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*Toki, she started out as this in [[http://akaichounokoe.deviantart.com/gallery/?q=Time+heals+no+wounds#/d4z3yme Time Heals No Wounds I]], before her redemption and change of heart.
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* WebVideo/TheNostalgiaCritic. He acts like a [[AdultChild brat]], often goes [[CuteButCacophonic annoyingly screechy when pissy]], and fights with everyone. But he [[TheChewToy suffers so much]] from the movies he watches, gets [[ButtMonkey walked all over at least once by everyone on the site]], and is a [[JerkWithAHeartOfGold good guy at heart]]. Taken UpToEleven in fanfiction where he's the [[LauncherOfAThousandShips fandom bike]], and they tend to do their very best to [[BreakTheCutie break him]] by humiliating him as much as they can.

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* WebVideo/TheNostalgiaCritic. He acts like a [[AdultChild [[ManChild brat]], often goes [[CuteButCacophonic annoyingly screechy when pissy]], and fights with everyone. But he [[TheChewToy suffers so much]] from the movies he watches, gets [[ButtMonkey walked all over at least once by everyone on the site]], and is a [[JerkWithAHeartOfGold good guy at heart]]. Taken UpToEleven in fanfiction where he's the [[LauncherOfAThousandShips fandom bike]], and they tend to do their very best to [[BreakTheCutie break him]] by humiliating him as much as they can.
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* The Green Goblin from ''ImAMarvelAndImADC''. The poor guy is always getting beaten up (even though this is PlayedForLaughs) and the object of his affection is hopelessly devoted to her abusive boyfriend (the Joker). Of course, he ''does'' treat his son like garbage.
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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] could be interpreted as one.
** Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their [[MarySue only flaw]].

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] could be interpreted as one.
**
one. Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their [[MarySue only flaw]].
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** WebVideo/AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.
*** Then [[ItGotWorse it gets worse]] when he takes his medicine, and ''becomes'' the [[FauxAffablyEvil hysterical but skin-crawlingly creepy]] persona. It's the ''better alternative'' than the horrible, miserable wreck of a man he'd be otherwise.

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** WebVideo/AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.
***
reason. Then [[ItGotWorse it gets worse]] worse when he takes his medicine, and ''becomes'' the [[FauxAffablyEvil hysterical but skin-crawlingly creepy]] persona. It's the ''better alternative'' than the horrible, miserable wreck of a man he'd be otherwise.
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*** Then [[ItGotWorse it gets worse]] when he takes his medicine, and ''becomes'' the [[FauxAffablyEvil hysterical but skin-crawlingly creepy]] persona. It's the ''better alternative'' than the horrible, miserable wreck of a man he'd be otherwise.


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** Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their [[MarySue only flaw]].
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YMMV sinkhole


* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[Wiki/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] interpreted as one.

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* WebOriginal/TheNostalgiaCritic. He acts like a [[AdultChild brat]], often goes [[CuteButCacophonic annoyingly screechy when pissy]], and fights with everyone. But he [[TheChewToy suffers so much]] from the movies he watches, gets [[ButtMonkey walked all over at least once by everyone on the site]], and is a [[JerkWithAHeartOfGold good guy at heart]]. Taken UpToEleven in fanfiction where he's the [[LauncherOfAThousandShips fandom bike]], and they tend to do their very best to [[BreakTheCutie break him]] by humiliating him as much as they can.
** [[DistaffCounterpart Perhaps fittingly]], WebOriginal/TheNostalgiaChick too. She's not too fond of empathy, treats BFF Nella like crap (even though Nella is a ButtMonkey professionally, it still counts), and her reasons for killing the [[TheCaligula Critic]] in {{Kickassia}} was purely for her [[TheStarscream own gain]] and has nothing to do with the others. However, she has awful self-esteem, had a [[HilariouslyAbusiveChildhood shitty childhood]], and there's been a few times where you can tell that she really does [[RomanticTwoGirlFriendship love her best friend]].

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* WebOriginal/TheNostalgiaCritic.WebVideo/TheNostalgiaCritic. He acts like a [[AdultChild brat]], often goes [[CuteButCacophonic annoyingly screechy when pissy]], and fights with everyone. But he [[TheChewToy suffers so much]] from the movies he watches, gets [[ButtMonkey walked all over at least once by everyone on the site]], and is a [[JerkWithAHeartOfGold good guy at heart]]. Taken UpToEleven in fanfiction where he's the [[LauncherOfAThousandShips fandom bike]], and they tend to do their very best to [[BreakTheCutie break him]] by humiliating him as much as they can.
** [[DistaffCounterpart Perhaps fittingly]], WebOriginal/TheNostalgiaChick WebVideo/TheNostalgiaChick too. She's not too fond of empathy, treats BFF Nella like crap (even though Nella is a ButtMonkey professionally, it still counts), and her reasons for killing the [[TheCaligula Critic]] in {{Kickassia}} was purely for her [[TheStarscream own gain]] and has nothing to do with the others. However, she has awful self-esteem, had a [[HilariouslyAbusiveChildhood shitty childhood]], and there's been a few times where you can tell that she really does [[RomanticTwoGirlFriendship love her best friend]].



* Tom of ''WebOriginal/EchoChamber''. While Tom is an ass to everyone and his excuse for being so is...weak, when he actually admits why he struggles, he shows a scared side. Especially obvious in "RomanticFalseLead", when Tom's reasons for loving Porn Girl is that she doesn't threaten, scare, or hurt him.

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* Tom of ''WebOriginal/EchoChamber''.''WebVideo/EchoChamber''. While Tom is an ass to everyone and his excuse for being so is...weak, when he actually admits why he struggles, he shows a scared side. Especially obvious in "RomanticFalseLead", when Tom's reasons for loving Porn Girl is that she doesn't threaten, scare, or hurt him.



* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[WebOriginal/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' understatement, [[WebOriginal/SCPFoundation [[Wiki/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.one.
----
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** WebOriginal/AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.

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** WebOriginal/AskThatGuyWithTheGlasses WebVideo/AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.
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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' {{understatement}}, [[WebOriginal/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.

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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' {{understatement}}, understatement, [[WebOriginal/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.
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** AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.

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** AskThatGuyWithTheGlasses WebOriginal/AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.
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* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' {{understatement}}, [[SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.

to:

* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' {{understatement}}, [[SCPFoundation [[WebOriginal/SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.
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* Both Zaboo and Bladezz from ''TheGuild''. The first is a StalkerWithACrush who's just so naive and well-meaning that Codex can't figure out whether she wants to ignominiously boot him out of her life or hug him. The second is a {{troll}} and a bit of a {{Jerkass}}, but he spends much of season 3 having incredibly nasty stuff happen to him.
** Also, Tink, although she's more Jerkass than Woobie.
** Zaboo is creepy and horrible with people, yeah, but he doesn't qualify as a JERKASS. Even when he does rude things, it's always done with the best intentions and a loving heart. He's just...super creepy. (And a complete Woobie.)
* Esau from ''{{Fanfic/Stray}}'', who could be described as Adamska's EvilCounterpart. He's a {{Tykebomb}} agent of the Patriots who initially comes across as a SmugSnake and does some rather cruel things in his efforts against the protagonists, but his back story is deeply unhappy. [[spoiler: And in true ''MetalGearSolid'' villain fashion, his death scene is [[AlasPoorVillain played for tragedy.]]]]
* [[http://www.youtube.com/watch?v=FJMazAXyV8w Jackie]] from the ''Jerry'' series. In the original short, she steals from the protagonist twice. In her own short, she cheats on her boyfriend, beats the shit out of several people, and ''maces'' a guy for giving her a flower because he was ugly. And, she gets kicked out of their house, has her suitcase stolen, gets sexually assaulted, gets mugged, becomes a stripper, breaks her ankle, gets sexually assaulted by her ''doctor'', does heroin, etc. The whole thing karmically balances pretty well.
* WebOriginal/TheNostalgiaCritic. He acts like a [[AdultChild brat]], often goes [[CuteButCacophonic annoyingly screechy when pissy]], and fights with everyone. But he [[TheChewToy suffers so much]] from the movies he watches, gets [[ButtMonkey walked all over at least once by everyone on the site]], and is a [[JerkWithAHeartOfGold good guy at heart]]. Taken UpToEleven in fanfiction where he's the [[LauncherOfAThousandShips fandom bike]], and they tend to do their very best to [[BreakTheCutie break him]] by humiliating him as much as they can.
** [[DistaffCounterpart Perhaps fittingly]], WebOriginal/TheNostalgiaChick too. She's not too fond of empathy, treats BFF Nella like crap (even though Nella is a ButtMonkey professionally, it still counts), and her reasons for killing the [[TheCaligula Critic]] in {{Kickassia}} was purely for her [[TheStarscream own gain]] and has nothing to do with the others. However, she has awful self-esteem, had a [[HilariouslyAbusiveChildhood shitty childhood]], and there's been a few times where you can tell that she really does [[RomanticTwoGirlFriendship love her best friend]].
** AskThatGuyWithTheGlasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason.
* Bitey of ''{{Brackenwood}}'' is a complete ass, going out of his way to ruin the day for Brackenwood's other creatures. It is eventually revealed that he acts out of jealousy. He can't stand seeing other creatures happy with their kin, and being the {{last of his kind}} compounds this jealousy.
* Captain Hammer, by the end of ''DrHorriblesSingAlongBlog''. He's a JerkJock who bullies the VillainProtagonist ForTheEvulz, and is only a hero because it's easier and it gets him laid. Then, at the end, we find out that, in his entire life, he's never before felt pain, and when he does, his response is to cry for his mother and run away.
** The aforementioned Villain Protagonist - Doctor Horrible himself - counts as well. [[CanNotSpitItOut Too nervous around the women he's attracted to to tell her]] that he likes her, gets brutally beaten up by Captain Hammer repeatedly, but he is still a CardCarryingVillain (not to mention his feelings for Penny can be interpreted in a [[http://karjack.livejournal.com/656327.html?format=light less sympathetic way]]).
* TalesOfMU is narrated by one of these, especially with regards to the prejudice and bigotry of which she is routinely the victim, but which she also routinely exhibits to others. To be fair, much of this was [[FreudianExcuse taught to her]] as she grew up by her KnightTemplar grandmother. But between the Mechans, the Arkhanites, Winnie, and just about anyone who disagrees with her, she gives as good as she gets on the {{Jerkass}} front.
* Tom of ''WebOriginal/EchoChamber''. While Tom is an ass to everyone and his excuse for being so is...weak, when he actually admits why he struggles, he shows a scared side. Especially obvious in "RomanticFalseLead", when Tom's reasons for loving Porn Girl is that she doesn't threaten, scare, or hurt him.
* Efeddre of ''[[GutsAndSass Guts and Sass: An Anti-Epic]]'' has a DarkAndTroubledPast where he was captured and tortured for nine years. He regularly verbally abuses the people who rescued him, but few feel like they can smack him because it's only been a year since he was rescued.
* If you [[PerspectiveFlip stretch the definition]] of "{{woobie}}" quite a bit, and keep in mind that "{{jerkass}}" is a ''[[OmnicidalManiac gross]]'' {{understatement}}, [[SCPFoundation SCP-682]] [[YourMileageMayVary could be interpreted]] as one.

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