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Jerkass Woobie / Theatre

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  • 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.