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  • Evillious Chronicles: Riliane Lucifen d'Autriche is the last princess of Lucifenia. When she was young, she was separated from her twin brother and suffered from memory loss as a result of exorcism. After the deaths of her parents, she was Lonely at the Top and only became further isolated as her tyrannical rule made her enemies. When the revolution breaks out, she's abandoned by all of her servants except for her twin brother, who reveals his true identity before getting executed in her place. Once she matures and realizes the depth of her cruelty, she spends the rest of her life regretting everything she's done and trying to atone. Despite her misdeeds, the sheer amount of humbling experiences she goes through and the fact that a lot of her tyrannical rule was due to Demonic Possession makes her a sympathetic figure.
  • Gorillaz's Murdoc rapidly grew out of Woobie status of any kind, but in his preteen days, he definitely fell into this category. According to Rise of the Ogre, he was a horrible child, but given that he was a victim of Financial Abuse and public humiliation by his father, suffered regular beatings from his brother, and claims to have lost his virginity at the age of nine, and it's horribly possible that he's not making that up, you can't help but pity him. His pitiable status resurfaces a little in his Pirate Radio broadcasts, during which he's perpetually drunk and rambling about how lonely he is.
  • Donato from Gian-Carlo Menotti's opera, Maria Golovin. He's a young man, blind from war, living with his mother and building birdcages. He's very lonely and he falls in love with a woman who lodges with them. Then he becomes fearful and jealous and has outbursts of anger, culminating in him grabbing a gun with the intent of shooting her.
  • Eminem's stage persona definitely comes off as one of these, and the man himself has not had an easy life. Sure, he threatens to kill his wife repeatedly, but there's no doubt that his life has sucked.
  • Likewise Tyler, The Creator's stage persona, and when performing as "Wolf Haley" or "Samuel" he brings it to Woobie, Destroyer of Worlds. Sometimes the man himself can be this, due to his obnoxious behaviour but somewhat serious Artist Disillusionment and genuine emotion in his music.
  • Pink from The Wall beats his wife and essentially becomes a Nazi-wannabe, but songs like "Bring the Boys Back Home" and "Hey You" remind us that there is a decent, redeemable person underneath all of that.

    Professional Wrestling 
  • Edge is arguably one of the best examples in modern wrestling history. True, his character did evolve a great deal over the course of his 2004-2010 heel run, but there was always one constant: an athlete who had worshipped the wrestling business since he was a boy and was determined to dedicate his entire life to achieving excellence in that field. Many of the things he said and did, while despicable in the most morally traditional sense, were actually quite reasonable, such as his justification for attacking John Cena after Cena had just barely survived a chamber match against five other men:
    Edge: I had a year-long contract for a WWE Championship match, was patient and bided my time until the moment was right, and now I reap the rewards. And sure, a lot of people didn't like it, but it was my right as Money in the Bank winner and there's nothing in the rulebook saying I can't do it.
    • Later, when he betrayed his Kayfabe wife Vickie Guerrero, it was easy to see that his motivation was not simply that he was a Jerkass but because he honestly couldn't keep his lustful desires in check (never mind that his Real Life affair with Amy "Lita" Dumas broke up his second marriagenote  in five years). Admit it: you were sad when Vickie (initially) refused to forgive him and, instead, basically sentenced him to death at the hands of The Undertaker.
  • Alex Riley, The Miz's personal attendant who is pretty much a Butt-Monkey. He got blamed for everything that went wrong for The Miz and got humiliated repeatedly. When Miz finally fired him, it looked like Alex was about to cry. But then he just attacked Miz instead.
  • Ricardo Rodriguez, personal announcer of Alberto Del Rio. While he joins in on any of Del Rio's malicious antics and even intervenes on his behalf, this also often leads to him acting as Rio's meat shield whenever he needs a diversion, with pretty much the entire roster taking sadistic pleasure in beating the living snot out of him, either to make a message to his boss or just because they hate the smug little weasel. Since he is an announcer, unlike other examples here, he can't really dish it back either, the pants shitting terror whenever he is cornered by a vengeful opponent is very evident.
  • Stephanie McMahon could qualify for this, as she's constantly and repeatedly been humiliated for years now. The biggest such moment being the promo where Chris Jericho and The Rock teamed up to make fun of her, which causes her to burst out screaming for them to stop and runs away crying.
  • Jimmy Jacobs of Ring of Honor fame is arguably a mix of Anti-Villain, Byronic Hero, and straight-up Jerkass Woobie, but mostly the latter. Jacobs crossed the Despair Event Horizon after falling in love with his manager, Lacey, and discovering that Love Redeems doesn't always work. He, along with several like-minded individuals, formed The Age of the Fall, half-cult, half-wrestling stable, dedicated to violently correcting what they perceived as injustices in ROH and society. They brutally beat Jay Briscoe and hung him upside down so that Jacobs could stand underneath him pontificating on his philosophy, all the while Briscoe's blood dripped down onto him. When Lacey fell in love with another man, Jacobs attempted to attack her on multiple occasions with a metal railroad spike. Jimmy Jacobs may appear to be an adorable emo boy, but he is actually a bloodthirsty hate machine.
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    Radio 
  • The Big Finish Doctor Who audio "The Boy That Time Forgot" simultaneously upgrades Adric to Jerkass Woobie and A God Am I: timey-wimey stuff leaves him stranded in an alternate universe of his own mind's making after the events of the Doctor Who serial Earthshock, eventually driving him to madness from loneliness, isolation, lack of humanoid contact, and a pretty massive sense of abandonment. By the time the Doctor and Nyssa find him, he's become an egomaniacal, old ( read, over 500 years old) man who thinks that the world should be at his beck and call (which, thanks to crazy math reasons, it kinda is), throws the Doctor into a giant spider pit just for fun, tries to force Nyssa to marry him, and has almost complete disregard for his genius insectoid subordinates' lives, even sending a squadron to kill the one he named after Tegan. Oh, and also there's the whole "wanting revenge on the Doctor for leaving him to die" bit. By the end, though, he's fully redeemed himself, even managing to pull off another Heroic Sacrifice.

    Tabletop RPG 
  • Warhammer 40,000
    • The Emperor. Let's say that the guy is a complete Knight Templar and Well-Intentioned Extremist who thought that Utopia Justifies the Means. He started the greatest war of conquest in man's history and wiped out thousands of human and alien nations in order to ensure mankind's survival. He wasn't the most exemplary and comprehensive father for his sons; mind you, he was betrayed by half of them, his empire was shattered by a terrible civil war which nearly annihilated mankind, got many of his family, friends, and loyal collaborators killed, and, in the end, after being mutilated and mortally wounded by his most beloved son and having to kill him during his final confrontation with the rebels, he had to be placed in a life-support mechanism which reduced him to a living corpse, having to endure thousands of years of watching and protecting the Imperium in the psychic-Hyperspace realm which happens to be a literal hell full of cosmic horrors...Oh, and time is relative in the Warp, so yeah, may have been an everlasting experience there, you feel sorry for him.
    • The Thousand Sons chapter is really noticeable amongst the space marines in general. They initially were not part of the Horus Heresy and even tried to warn the Emperor when they got word of it. Cue the Space Wolves charging in and trying to exterminate them due to the high number of psykers and mutations which was determined illegal. They fled to the Eye of Terror due and, ironically, become part of the thing they were fighting. As a last ditched effort to save themselves, Ahriman casted a spell that accidentally wipes the bodies of his brethren, forcing them to a mindless existence as Animated Armor. Space marines are universal in their Jerkass Knight Templary, but you really gotta feel sorry for these guys.
      • Konrad Curze, the Night Lords Primarch. Curze was dropped on a planet of endless night, ruled by criminals through force and fear. He survived in the sewers eating vermin and, occasionally, people. He went mad as a defence against what he saw and wanted to do the right thing but how can you do that on a world where everyone is an evil bastard who just solves their problems with violence and intimidation? And then later after bringing Nostromo to heel, it decays into a lawless hellhole worse than it ever was in his absence and the only justification for his actions falls apart, sending him over the deep end. Add in the premonitions that haunted him throughout his life, and he never stood a chance. Curze was a monster, but he was never given a chance to be anything else. He lived a life without love or hope and in the end he let an assassin kill him.
    • Humanity in the GrimDarkness of the far future in general arguably fits. Their empire is overall xenophobic, repressive, stagnant, and warmongering, but the average person is rather ignorant, lives a stale life devoted to working to advance the Imperium's military in some way, lest they attract the attention of their superiors, is being constantly kept in the dark from their own government until it's too late for them to do anything about it, their government doesn't recognize them as individuals due to the gigantic size of the Imperium and its ObstructiveBureaucrats, and is, by all means, a plaything to the Imperium's High Lords of Terra. And the government's actions are arguably justifiable because everything else really can kill all human beings if they don't devote all their effort into their military and keeping it that way.
    • And then there are the remnants of the Eldar, whose entire civilization was Mind Raped into oblivion, and now they're dying out and have to live out painfully repressed lives because an Eldritch Abomination is out to eat every one of their souls and send them to a Fate Worse than Death for all eternity.
    • As of fifth edition, the Necrons robotic unlives now suck as badly as everyone else in the galaxy, having been forced into a Fate Worse than Death after being tricked by their gods and watching their empire fall apart through no real fault of their own. They would probably be the Eldar's best friends, except they're even more xenophobic and posses the universe's largest entitlement complex. And that's not getting into destroyers...
  • Pathfinder: Seltyiel, a half-elven Pretty Boy (or even borderline Captain Ersatz of Elric) magus who's canonically the paladin's pet project. Yes, he's also canonically evil...but with a backstory like that, you almost can't blame him.
  • Exalted: It's hard not to feel at least a bit sorry for Eye and Seven Despairs, who, in the First Age, found himself teamed with a group of Curse-maddened sadists and ended up Driven to Suicide. As a Deathlord, he'd be a Woobie, Destroyer of Worlds if he wasn't so easily distracted by tormenting a handful of people who look like his former Circlemates.
  • Werewolf: The Apocalypse has Rorg, the Incarna of the asteroid belt. He's a savage, unstable deity, but it's difficult not to pity him. His realm was destroyed by the Wyrm eons ago, and he's been in physical and psychological agony ever since.
  • Nightmare's Angel of Chuubo's Marvelous Wish-Granting Engine is relentlessly arrogant, selfish, rude and opinionated. On the other hand, Nightmare's Angel is also a desperately lonely teenager haunted by nightmares, cursed with forebodings of doom, and unable to express any desire for friendship without being literally physically weakened by it.

    Theatre 
  • The eponymous character of Oedipus at Colonus is a former great king who killed his father, married his mother, blinded himself when he discovered this, and is reviled by all but his two daughters, who get abducted midway through the play in an attempt to force him to return to Thebes. On the other hand, he's still immensely stubborn and calls down a curse on his own sons so that they may die in the coming civil war (and it works).
  • Gabe from Next to Normal just wants his family to love him. Unfortunately, he expresses it by trying to drive his mentally ill mother to suicide. That is, if you actually believe his presence exist or he's just a manifestation in the character's head.
  • Cyrano de Bergerac: Cyrano. His attitude with the Buffet-girl, Raguenau, and the nuns show us that he is a Jerk with a Heart of Gold. His attitude with anyone who is not a Gascon show us that he is definitely a Jerkass, and the universe of the play is constantly placing him in unpleasant situations. In Act I Scene V, he reveals to his best friend Le Bret a hidden, softer side, talking about how he feels that he never will be love by Roxane because his enormous nose:
    Le Bret: Well, but so much the better! Tell her so!
    She saw your triumph here this very night!
    Cyrano: Look well at me — then tell me, with what hope
    This vile protuberance can inspire my heart!
    I do not lull me with illusions — yet
    At times I'm weak: in evening hours dim
    I enter some fair pleasance, perfumed sweet;
    With my poor ugly devil of a nose
    I scent spring's essence — in the silver rays
    I see some knight — a lady on his arm,
    And think "To saunter thus 'neath the moonshine,
    I were fain to have my lady, too, beside!"
    Thought soars to ecstasy... O sudden fall!
    — The shadow of my profile on the wall!
    Le Bret: (tenderly) My friend!...
    Cyrano: My friend, at times 'tis hard, 'tis bitter,
    To feel my loneliness — my own ill-favor...
  • Shylock in The Merchant of Venice. What with the abuse heaped upon him by his enemies, his soul-tearing agony at the loss of his daughter and his dead wife's ring, and his hellish-yet-admirable persistence against the odds, it's easy to cheer for him and forget that his main goal is to literally scoop the heart out of a man in open court, in front of all the victim's friends. He wants to do this partly because he's taking out his losses on the guy (who seems not to have been in on the elopement to begin with), partly because the guy is a business rival and killing him will help turn a profit, and partly because he just hates the guy. The effectiveness of this obviously depends on the actor, but in some of the best stagings, Shylock's final exit is the ultimate Tear Jerker and makes you want to follow him and give him a big comforting hug.
    • Malvolio in Twelfth Night is another Shakespearean example. Because of his attempts to enforce Puritan values on his mistress' household, he is publicly humiliated when the other characters play on his secret affection for Olivia, getting him to play the fool in an attempt to woo her. Olivia even acknowledges that they went way too far in humiliating him.
  • The eponymous Medea. She literally gave up everything to be with Jason — her country, her family, her position...she even arranged her own brother's death so they could get away. Then Jason turns around and ditches her for a younger, prettier Greek girl, primarily for her father's prestige and money. He ever-so-magnanimously says that Medea can still be his mistress. She flips the hell out, and while her actions are horrible (particularly in the most common version, where she murders her children to get back at Jason), it's hard not to feel sorry for her.
  • Sure, Thyestes stole his brothers wife and attempted to usurp the throne. But Atreus' revenge is sheer evil. He pretends to pardon Thyestes and then serves him his own sons for dinner. Thyestes is a broken man at the end of the play.
  • Mrs. Neille Lovett from Sweeney Todd: The Demon Barber of Fleet Street. She's a widow and a Love Martyr who wishes to have a new lover, and that's none other than the titular Villain Protagonist himself. She also mentioned that his wife, Lucy, was raped by Judge Turpin, and eventually committed suicide while she was away. However, when Sweeney went Ax-Crazy and seeks vengeance on everyone in London, Lovett initiates her plan to make meat pies out of corpses from Sweeney's victims. Though by the end of the story, after screaming when Turpin moved around for a little while before dying, Sweeney notices her. However, her lies was found out when the Beggar Woman's dead body is none other than Lucy herself. Sweeney, in anger, pretends to forgives Lovett before throwing her into the oven, and was later killed by Tobias Ragg.
    • Benjamin Barker - better known as the titular Villain Protagonist - Sweeney Todd, also counts. Falsely accused of a crime he didn't commit, and sentenced to life in prison, he was sent away to Australia; only to return 15 years later. Though after his first shot of revenge on Turpin failed, he went Ax-Crazy and seeks vengeance on everyone in London. Sweeney went over the edge, however, when he finds out that he accidentally murdered the Beggar Woman, who is none other than his wife, Lucy. Furious, yet calm, he dances with Mrs. Lovett, pretending to forgive her, before hurling her into the oven. In remorse, he cradles his wife's dead body for a few minutes before he gets his throat slitted by Toby, who went mad after finding out what's in the meat pies.
  • Mr. Zero in The Adding Machine. Being a Lazy Husband at home and an unimaginative drudge at work, as well as an all-around bigot prone to fits of murderous rage doesn't overshadow all the suffering he's endured in one reincarnation after another.
  • Freddie (aka The American) in Chess is at best brash, deeply obnoxious, and unstable. He becomes more and more pathetic as he unravels over the course of the story and his Villain Song, Pity the Child, reveals how his abusive upbringing shaped his personality.

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