- In Alfred's Playhouse, Dictator Alfred is the Ax-Crazy megalomaniacal evil half of Alfred's Split Personality. Alfred was sexually abused as a child, and imagined himself in a happy fantasy world to escape what was happening to him... But it turns out that Dictator Alfred ended up being conscious for him and had to take the abuse that Alfred couldn't. He ended up being very cold and vengeful because of this, and now wants to Take Over the World and force everyone to obey and love him. Yeah, it's that kind of series.
- Atop the Fourth Wall has Jaeris (aka the Gunslinger). Arc Villain he may be, but once you know his motives, its hard not to feel sorry for the guy.
- There's also Margaret, the girl in Linkara's Magic Gun. The gun was created by Margaret's parents torturing and killing her as a sacrifice to their God, and in exchange she drove everyone who took up the weapon who was responsible for her death to madness and death.
- In The Blackrock Chronicles, Rythian runs the risk of becoming this, after Zoey Proasheck leaves to go elsewhere and Duncan Jones and Sjin harass him. While dangerously destructive and nearly as bad as Duncan and Sjin were (for context, their mini-war pretty much destroyed the first Yogscast Tekkit server), there's no doubt that he's gone through a lot of hardship.
- Dr. Horrible from Dr. Horrible's Sing-Along Blog becomes a combination of this and Well-Intentioned Extremist at the end of when his Despair Event Horizon caused by Penny's death plunges him into complete villainy
- Glitchtale has a truly disturbing example, given how near-universally reviled the character is due to their actions, with a huge amount of viewers (and virtually the entire cast of characters) still not knowing the truth. Despite being portrayed as a complete and utter Hate Sink and The Sociopath in the series proper, Bête Noire of all people has by far the most screwed up existence out of the entire cast. Brought into existence using a murdered girl's body and the soul of said murderer, she must fulfill her mission to wipe out all monsters and rule over humanity to prevent another devastating war between the races from potentially happening in the future. Oh, and she was created specifically to not have emotions such as love or empathy so as not to distract her from her purpose, meaning that she never had a chance at being a good person. Ever. Even if she were able to feel that desire. Furthermore, because this leaves her as a psychotic sadist, her horrific screeching demise is treated as a straight-up extremely satisfying triumph when the truth is she could hardly even be held responsible for her own evil. Even Word of God loathes her and enjoyed butchering her as excruciatingly as possible. Nobody found out the truth of her tragic existence and Papyrus was the only one who felt anything resembling pity for her, stating that he did not want to hurt her despite all that she did, reemphasizing his nature as a Badass Pacifist. He wishes he could have wanted to kill her, since he might have saved his family a lot of pain and misery.
- Amon in the sketches of something that may become Korra Abridged."All I ever wanted was to someone laugh on my jokes, just once, but no one ever did. So I decided if I couldn't live my dreams, than I take everyone else dream by ridding the world of bending."
- Ilivais X's protagonist, Iriana Estchell, is this all the way. Her life essentially boiled down to being converted into a Wetware CPU by an abusive instructor who loved taking advantage of how pleasure is felt as pain for her, interspersed with more flat-out rape which was meant to promote her love-based Drive Core to consume her. She finally escapes with Seyne's help and has in her possession an advanced Super Prototype Humongous Mecha powered by a Perpetual Motion Machine. "Destroy absolutely everything in the Aztec Empire" is now #1 on her list of priorities. There's only the slight problem of how she's not really THAT good at it, and said Aztec Empire isn't inherently evil at all.
- The Storyteller from Off the Page and into Life. All she wanted was to be able to see her deceased friends again...
- The Nostalgia Critic seems to have a Split Personality problem, so you honestly do feel bad for him when he looks like he might cry after realizing an explosive tantrum of his blew up a city.
- Ma-ti, a semi-regular character of TGWTG until the third anniversary, has become this in the year between the third and fourth anniversaries. He literally became a cosmic entity hell-bent on wiping out the whole TGWTG universe through a decision he forces upon the Nostalgia Critic.
- Alluded to by Doug Walker in his Avatar: The Last Airbender vlogs, admitting that if he had Fire Nation Powers he'd probably use them as revenge.
- Red vs. Blue has one in the form of their Arc Villain for Season 15, Mark Temple. Originally part of the oldest groups of Sim Troopers to exist - and in fact, the template that was used for the Blood Gulch Crew, Temple was forced onto the blue side while his childhood friend Biff was placed on the red side. They hatched a plan where Temple would shoot off Biff's finger to earn him a medical discharge and a way to return to his pregnant lover, only for Carolina and Tex to show up and play capture the flag with their teams, with the pair of troopers following them to get witnesses for the finger plan. Suddenly, Carolina grabs Biff and uses him as a human shield. Tex then throws the flag pole like a javelin at Carolina, who deflects it ... causing Biff to get impaled through the stomach and die. The revelation that the Sim Troopers were essentially slaves to Project Freelancer caused Temple to lose his sanity, recruit the surviving Sim Troopers and go around killing everyone involved with Freelancer.
- RWBY: Salem yearned for freedom, locked in isolation by her father until rescued by the legendary hero, Ozma, with whom she fell in love. Devastated when he dies from sickness, she begs the God of Light to resurrect him and then, when he refuses, the God of Darkness. Restoring Ozma provokes a confrontation with the God of Light, where Ozma is repeatedly killed and resurrected in front of Salem's eyes until she turns on the two gods in rage. They punish her with immortality to prevent her reuniting with Ozma in the afterlife until she learns the value of life and death. Driven to Suicide, but unable to die, Salem raises an army against the gods; in retaliation, the God of Darkness destroys humanity before both gods depart the world, leaving Salem to exist alone for years until she tries to end her curse by throwing herself into the God of Darkness's Pools of Annihilation. She's instead transformed into a being of pure destruction. When humanity returns to the world, the God of Light reincarnates Ozma to guide them to redemption. Salem finds freedom by raising a kingdom and family with Ozma until he becomes so worried by her destructive urges that he absconds with their children. Confronting him, their ensuing battle destroys her freedom, home, kingdom, and children. Now Salem is determined to ruin Ozma's mission and end her own life by destroying the entire planet, trapping them forever in a war of hate that has no end.
- SCP Foundation: The Foundation has several SCPs like this.
- SCP-239 seems destined to become one, due to what had to be done to contain a little girl with godlike levels of reality warping ability and no comprehension of the fact that Reality Warping Is Not a Toy.
- In a shining example of Unintentionally Sympathetic, some headcanon interpretations of SCP-682 paint the quazi-reptilian Omnicidal Maniac as this trope: it's implied that it comes from a radically different reality and finds life as we know it inherently abhorrent.
- One of the oddest is SCP-1609. Formerly a helpful teleporting magic chair. Now a vengeful, lethal, teleporting pile of woodchips following an ill-advised act by the GOC.
- The Spoony Experiment: How can anyone not want to give Dr Insano a hug after his plans go wrong?
- Monster X in Toho Kingdom Toons. Sure, he's well-aware that the fangirls call him a "Woobie", but he also says that he's not giving up without a "fighty-wighty"
- The Weather: Alan, according to one skit, has just had a terrible, terrible life, suffering abuse and misfortune at every turn and genuinely hating himself and others for it. His reflection convinces him that they should go out and kill the people who hurt him with anything they have on them, to which Alan agrees.
- Miles Prower in Where Was My Hero...? was bullied and tormented by everyone he knew and having never met Sonic in this timeline never had anyone showing him any kind of love. One day he finds an injured bird and taking pity upon it nurses it back to health, growing fond of it, he turned it into his Living Emotional Crutch, just when it looked like his luck was turning around, his two main bullies show up to destroy yet another of his creations and accidentally kill his bird, the poor boy, having crossed both the Despair Event Horizon AND the Rage-Breaking Point at practically the same time, reacts violently, very violently. Even after that, he still tried to be a hero instead of a force of evil, but when Sonic disapproves of his "methods" he gives up on being a good guy. By the end, as he lays dying, he starts reminiscing about Fond Memories That Could Have Been, made all the more tragic by the fact that this memories do occur, in the canon timeline.
- Worm: Several villains who have done disgusting and horrible things have some truly shitty backstories such as how Riley became Bonesaw, Bitch's entire life till the point she met Taylor, and the things Heartbreaker forced Regent to do as a kid.
- Poor Scion. And what Taylor does to herself and everyone else to stop him.
- Zorc from Yu-Gi-Oh! Abridged. Who's that crazy kook destroying the world?
Woobie Destroyer Of Worlds / Web Original