Jerkass Woobie / Web Animation

• Bitey of the Brackenwood series is one massive Jerkass, who loves nothing more than to ruin the day of the fellow inhabitants of Brackenwood. Beneath the surface however, is an intelligent creature stuck in a world of simple animals, no other Dashkin to associate with, resentment over seeing other creatures with happy families, and a simple desire to have friends.
• Max from Camp Camp officially becomes one following "Parents Day". It was hinted before that his parents were neglectful, but this episode confirms it. He spends most of the day being a brat and acting out of jealousy upon seeing all the other kids hanging out with their parents and other loved ones. Then, not only do his parents never show up, it's revealed they didn't even sign him up for a specific activity. They just didn't want him around. The reminder of this is enough to bring Max to tears.
• Dr. Havoc's Diary: The titular character himself. His ideas to Take Over the World constantly go down in flames, his wife constantly cheats on him and eventually leaves him, his daughter is both ditsy and dismissive, and his arch-enemy is a womanizing Hero Antagonist. But of course, Dr. Havoc is still quite a bit of a dick himself, being the Villain Protagonist not above killing innocent people and all.
• Epithet Erased:
  • Mera is pretty terrible to Indus and rewards a child for helping her by planning to steal that child's powers. However, between an epithet that leaves her in constant pain and a background that indicates she was kept alone in her house as a child for fear that she would injure herself while playing with others, there's still a significant amount of sympathy for her out there despite her actions.
  • Zora is often quite petty and unpleasant, and even her resentment toward her extremely powerful epithet is hard to take that seriously given how much she loves to abuse it, but it's hard not to feel at least a little bad for her when "Great at Cowboy" confirms her origins, specifically, that her parents found a treasure and were murdered for it.
  • Lorelai Blyndeff is a tremendously selfish and entitled brat, but as Epithet Erased: Prison of Plastic continues, it becomes increasingly clear that she's ultimately just a child dealing really badly with trauma and guilt, isolating herself in her dream bubbles because she's afraid that her power killed her mother. By the end of the final battle, her illusions have been stripped away - both in the sense that the dream bubble is crumbling, and that her main character syndrome and ability to continue deceiving herself have taken a beating - and she's reduced from a menacing antagonist to just an isolated, immature kid who's destroyed one of the last relationships that meant anything to her, with her sister, through nothing more than her own selfishness and irresponsibility.
• FreedomToons: While both are depicted as massive hypocrites and does not in any way endorse their policies, it has devoted a handful of episodes to stressing how Bernie Sanders and Elizabeth Warren were treated rather poorly by their own party during the 2020 Democratic Primaries.
• GoAnimate: Caillou is a near-sociopathic brat who treats his sister like shit, constantly misbehaves at both school and at home but at the same time, his dad is often horrible to him and punishes him for petty reasons, his Mom encourages his dad to abuse him, his teacher also punishes him for petty reasons, his classmates, who instead of trying to tolerate his behavior and see past it, rat him out at the drop of a hat or insult him, so at the end of the day, can you blame him?
• Flippy from Happy Tree Friends. He's an adorable bear who suffers from severe post-traumatic stress disorder due to his time in war. While his "good" side tends to be one of the kinder and more sociable of the Tree Friends (aside from moments of cannibalism), his "evil" side will emerge whenever he sees or hears something that reminds him of war or death. Once in his evil state, he turns into an Ax-Crazy killing machine, slaughtering everyone around him in sadistic glee. One episode had him getting some therapy in an effort to overcome his disorder but the doctor was the Too Dumb to Live Lumpy who's stupidity prevented him from effectively helping Flippy. He's also just as much a Chew Toy as the rest of the cast (meaning that he tends to get killed in horribly gruesome ways if he's not the one doing the killing) and is shown looking terrified every time he comes out of his Ax-Crazy states to see the violence that he's committed against his friends.
• Angel Dust from Hazbin Hotel. While he is a jerk and the only reason he is staying at the hotel is because he wanted free room and board, he is also revealed to be in an abusive relationship with Valentino and his drug habit and behavior is hinted to be an attempt to make his pain stop.
• Inanimate Insanity has MePhone4. The episode "Mine Your Own Business" reveals that in his early days he was often physically and emotionally abused by Steve Cobs, and it was bad enough that Me Phone eventually got rid of the memories.
• The Most Popular Girls in School:
  • Mackenzie, as of Episode 18. She gets her bald spot diagnosed and is especially torn when the doctor told her she's suffering from Female Pattern Baldness. She's utterly helpless when she tried to regress her anger in front of a rivaling cheer squad.
  • Than. Completely obnoxious, creepy, and insufferable, but it's clear he really does just want the football players to like him.
  • Brittnay would also count, if you feel sorry for her because her car got blown up by Mackenzie.
  • The entire squad (mostly sans Trisha for the Jerkass part) as of season 3. Sure, they may be giant bitches, but the New Year's Eve episode completely highlights the friendlessness the squad had going on and as of episode 40, they are so desperate for new members, they just hire anyone they know regardless of who they were.
  • Shay van Buren, definitely—if you side with her over the Cheerleaders. She's been through a lot of crap, when you think about it.
• Natsumi from Natsumi Step! She's a Woobie for commiting suicide and going to Hell, and a Jerkass for murdering her boyfriend.
• Red vs. Blue:
  • Church. Oh, so much. He's the universe's Butt-Monkey, but he's also a complete jerk to everyone, so you can't help but feel sorry for him and laugh at him simultaneously. In season six you learn about his torture at the hands of the Director, which drove him to insanity.
  • Agent Tex, to a lesser extent. She's got a frequent habit of backstabbing the Blues (though this is mostly Played for Laughs), and during her time at Project Freelancer she was an antisocial jerkass (albeit with a softer side). But after an operation to retrive the armour of CT goes wrong, she discovers the fact that she is an AI, not a real human being, then tries rescuing the Alpha but can't help him because he's too broken to come along with her, before being chased away by Sigma, who has now taken over Maine's mind. After this, she gets killed by Donut, loses one of her few friends left from her Freelancer days (York, if you must know), then gets wiped out by an EMP unit, brought Back from the Dead involuntarily, fails to discover what her purpose in life is, loses a fight to the Big Bad Duumvirate of Season 8 because she's always doomed to fail, then gets wiped from existence.
  • Agent Maine as well. While berserk, he's loyal to his teammates. Then he takes a sniper shot to the throat, followed by several pistol shots, making him The Voiceless. After this, he gets given the AI Unit known as Sigma, who completely takes over his mind and takes the Axe-Crazy part of him further. This ends up turning him against his friends and completely erasing the person he used to be, to the point that he forgets who he was and is left following a pointless mission.
  • Towards the end of Season 10, the Director starts growing shades of this. He's always been quite the Jerkass, but then you finally see him in the present. He endlessly watches the last video of his dead girlfriend, who he has been trying since her death to rebuild. The most significant copy of which rebelled against him and destroyed everything he had built. He also learns that his daughter has been relentlessly hunting him with the intent of murdering him for his crimes. Plus the epic Shut Up, Hannibal! by fellow Jerkass Woobie / torture victim Church about everything horrible he has done. And then it's almost 100% certain he was Driven to Suicide immediately afterwards. Yikes. Can't help but feel sorry for the guy, despite all the horrible things he's done.
• RWBY.
  • Whitley Schnee. In all of his appearances, Whitley is portrayed as a snobby little shit, with Weiss taking satisfaction when the boy gets shut down in some way. When she confronts him about his knowledge that Jacques would disinherit her if she became too uncontrollable, he merely states that it's foolish to oppose their father's wishes. When Willow later indicates she wants Weiss to help Whitley escape just as she and Winter have been able to, Weiss points out that Whitley wants nothing to do with her. Willow reveals that's because Whitley was left all alone, at the mercy of an abusive father and alcoholic mother, when his two sisters left home. Unlike his sisters, Whitley has no Semblance to give him an escape route through the Huntsmen Academies; he's therefore had no choice but to allow Jacques to turn him into what he wants: a mirror image of himself. When Jacques is arrested for his crimes due to a combination of Willow and Weiss's actions, Whitley watches as his father is led away in handcuffs, huddled into a tiny ball in the middle of the grand staircase. It's the first time he's shown to be as alone and abandoned as Willow earlier described. However, freedom from Jacques allows him to grow out of his Jerkass traits as he takes command of the company resources to help the heroes save the kingdom's people, digging the heroes out of their Heroic BSoD in the process.
  • James Ironwood. After Volume 3, he begins Slowly Slipping Into Evil; after the Battle of Beacon triggers his PTSD, his behaviour grows increasingly paranoid. He is so determined to protect his kingdom from Salem without making Leo and Ozpin's mistakes that he can't see the mistakes he makes through fear and mistrust. After successive manipulation by Watts, Tyrian and Cinder, he snaps; unable to handle the protagonists' withholding information from him and Salem showing up with a massive army of Grimm, he turns on his allies, Mantle and even his subordinates, ultimately dooming the kingdom he's trying to save. He dies alone and broken, abandoned by the heroes and dismissed by the villains.
• Simon's Cat: Poor Simon's Cat, he might be a little mischievous by demanding attention to his owner. But he didn't really deserved all the pain he had brought from numerous episodes. Even Simon had hurt him in numerous shorts such as Fish Tank and others. It's no wonder why Simon's Cat ran away from his owner in Missing Cat series
• X-Ray in X-Ray & Vav. He's a self-serving egotist who feels threatened whenever someone does better than him and he goes out of his way to attempt to one-up them. Until the episode "The Madness of the King", where we find out he has some major Parental Abandonment issues due to his dad up and leaving him and his mom and X-Ray is utterly terrified of Vav leaving him in favor of reporter Ash.

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