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Examples of Jerkass Woobie in Fan Works.
- Rika Nonaka from the Tamers Forever Series. Oh dear god, RIKA!! She is self-centered and mean, with an outrageous competitive streak. But it is physically impossible to read Silent Sorrow and not have your heart ache for her after seeing what the author puts her through.
- In the Twilight fanfiction The (Not So) Short Second Life of Bree Tanner and its companion piece Ashes through an Hourglass, the offered back story of the Volturi's evil twin enforcers, Alec and Jane, helps rationalize their monstrous personalities in ways that elicit understanding and pity from the readers without undermining their sinister deeds. This more applies to Alec, though, since he has been featured far more than Jane and has demonstrated occasionally redeeming qualities through an amoral lens.
- Another Twilight fanfiction: Luminosity.
- Allirea is at best amoral For Science!, and once sent a five-year-old to be tortured. She also has a personality-based power that allows her to hide and a Stalker with a Crush who regularly kidnaps her. And, since powers are personality-based, that means that what Allirea probably wants the most is some time by herself.
- Chelsea is a Mind Rapist, and screws up people's relationships regularly. She also has a desperate need to be loved, to the point that anyone she passes who doesn't love her disturbs her.
- Dawn Schafer from the Babysitters Club fanfic When Forever Wasn't Enough. She starts out as the closest thing to an Alpha Bitch the story has, attempts to further drive the already-existing wedge between the former BSC members, and is incredibly self-absorbed the point where she neglects Stacey's growing depression and accuses her of being the self-absorbed one. However, she is also shown to be struggling with self-esteem issues, and longs to go back to California where she feels she belongs. But the part where this trope really kicks in? After Stacey's suicide, Dawn is so devestated that she takes her grief out on the other girls and accuses them of not being there when Stacey needed her (pot, kettle; kettle, pot). While she continues to go through the stages of grief, she grows more rebellious and refuses to acknowledge that she wasn't there when Stacey needed her...until the girls start reading each suicide note Stacey addressed to them, and Dawn realizes that she wasn't there for Stacey when she needed her, which drives her to tears.
- The Penguins of Madagascar fanfic Princess shows Julien with a bit of this. He's still his usual ditzy egotistical self, but he's going through a lot. He's Transsexualism, and nobody around him knows enough about the condition to think of it as a legitimate problem.
- The Green Goblin from I'm a Marvel And I'm a DC. The poor guy is always getting beaten up (even though this is Played for Laughs) and the object of his affection is hopelessly devoted to her abusive boyfriend (the Joker). Of course, he does treat his son like garbage.
- Fluttercruel from the Pony POV Series. She is most certainly a Jerkass, but that's not entirely her fault as she was created by Discord and the only thing she came into existence knowing was how to be mean and cruel. Fluttershy manages to guide her from a complete Jerkass to a Jerk with a Heart of Gold (and in the Bad Future where this never happened, she apparently "grew up" into an outright Complete Monster). On top of that, due to how she came into being, she just sees herself as a "Fluttershy ripoff" and is physically incapable of having a life of her own, since, no matter what, she's just sharing Fluttershy's body and looks identical to her. She doesn't even consider herself alive. Yes, she's a jerk, but it's impossible not to feel sympathy for the poor girl.
- Angel, from the AU Roleplayverse Otherborn, is a half-demon who physically, mentally, and emotionally abuses his charge, Namine, who he claims to be in love with. In fact, he's come close to pushing her over the Despair Event Horizon more than once, and the general reaction to this was to declare him a Complete Monster. It Got Worse when he was revealed to have killed his best friend in a jealous rage over the girl they both liked. And then... well, then the author started writing oneshots and revealed that Angel was, actually, so completely broken by this event that he literally went crazy. Namine was the only person who could put him back together again, but the damage done to his psyche was so immense that his demonic instincts began to take over, turning him into the Jerkass he is today. To the point where when Namine's abusive parents kidnap her back to their mansion, Angel goes into a catatonic state where the only thing he is capable of forming into a coherent thought is that he wants to die. The poor guy just seriously needs a hug.
- In Connecting the Dots, Sasuke spends the first half of the fic with one foot over the Moral Event Horizon, but after an unfortunate encounter with Kyuubi-Naruto, gets a visit from The Spectre who gives him an epic "The Reason You Suck" Speech and then strips him of his chakra...In the middle of GothamCity. No prizes for guessing what happens next.
- New Dawn: Shuuji Muzoku / Kazeshima. Emotionally reclusive, a bully early on, and does not really say much when him saying something might help. And he was abused to an utterly horrifying degree by his father, went through Cloning Blues due to that bastard The Seer, learned the sister he is trying to save might not even exist, goes temporarily crazy and utterly shuts down, only concentrating on whatever is the biggest threat this week.
- Queen Anathema herself. The Big Bad, yeah, but what she wants is to just make a Utopia, and she has forgotten the costs of this due to grief at her lover's passing, she had to kill her own best friend when he turned against her and tried to shoot her numerous times, calling her a wretched villain for what she did. All she wants is love. Not to mention she is being manipulated by nearly everyone around her, even her most loyal man has betrayed her in the backstory, leading to a violent persona taking over and trying to rule through fear.
- Shira. Raised as a girl to demean him by his psychotically misogynistic father, his mother was always out drinking and when she was home, she and his father always fought and ripped and tore at one another with their bare hands, leading to Shira getting a pretty nasty idea about what love really is. And when he came out as bisexual...it only got worse. Both his parents tried to drown him in a lake, while saying, "We love you too much to let you grow up a faggot." His discovery of his spell core in that very lake resulted in him accidentally killing both of them...and being psychotically devoted to killing, because otherwise he thinks they'd emerge from the lake as ghouls.
- Rai-Dei Kurai. Yeah, he is basically Slenderman or something, annihilating almost everyone who knows about him. This is because he was not always an abomination. He was once a man, but was badly distorted by Stagnant Mana he tried to use to defend his mother and little brother from a murderous mob during the medieval times, as they were thought to be witches. He was haunted by the voices of those who died in the ensuing chaos of his ascent to One-Winged Angel, and wants to believe all the evil in the world can be traced back to him. He believes that the entire world, so inundated with evil due to him, needs to be purged, and is so crazy its no wonder he and Katherine Daille got along so well. He actually started to revert to a normality, but when Katherine was abused more fiercely, he felt that he could not fail a loved one again...
- Mare Do Well from the My Little Pony Friendship Is Magic fanfic The Games We Play. Not only is she devious, selfish, and manipulative, but she delights in messing with Rainbow Dash's head as much as possible. She's also a desperately insecure Stepford Smiler with No Social Skills who just wants Rainbow Dash to like her.
- Dodger in Dodger and Company. Much like the film, he's snarky, cocky and sometimes prone to arguments, but his past is troubling. As a puppy, his mother, Annie, was forced to abandon him to protect him from his father, Duke, and lived on the streets before Fagin took him in.
- Light in A Cure for Love. He really does care deeply for L and loves him very much but things just aren't working out too well for them because Light is a crazy mass-murderer who wants to be God. Misa as well- she too is very much in love but her affections for Light are not returned and he ultimately betrays and killed her before she can kill L. Also V after learning her tragic backstory. And then there's Mello who is a Jerkass but then his mother and his boyfriend are killed on the same day.