Jerkass/Theatre

Freddie, the American champion in the musical "Chess," certainly fits the bill. Throughout the plot, Freddie engineers offensive publicity stunts to get more money, constantly abuses Russia and his opponent, mocks/manipulates his second, generally acts like a whiny little child, and eventually breaks down after he loses the championship. Moreover, he's also violent and sensitive, making him easily provoked. Yet, oddly enough, he (arguably) doubles as The Woobie, considering he sings an entire song called "Pity the Child."
Bertram, Count of Rousillon, in All's Well That Ends Well. Because he is married to a peasant girl (in the Distaff Counterpart of the Standard Hero Reward), he rebuffs her, saying he will only bed her when she can prove he has gotten her pregnant. Then he goes off to fight in one of the wars between Italian states.
Oh, Henry Higgins from Pygmalion! So very, very much! To wit: when he first meets the heroine Eliza he insults her accent even as she's trying to scrape enough money just to pay her rent; and he's endlessly patronizing and insulting to her when she comes to him for speech lessons. He makes no bones about the fact that other people annoy and bore him; and most of his interactions with other characters involve him insulting them, bullying them, challenging them, complaining about how bored with them he is, or else just bluntly identifying their accents. What's satisfying, though, is that the characters do notice this, and every single one of them Lampshades it when they remind him to have better manners.
- In a potential case of Misaimed Fandom, the musical version My Fair Lady actually makes him something of a He-Man Woman Hater (Misaimed Fandom because a key point of his personality in the original play is that he doesn't at all discriminate in his treatment of anyone-- he's just horrible to everybody around him)! The musical also attempted to soften him into something of a Jerk with a Heart of Gold in an attempt to make romantic overtures between him and Eliza okay....
Stanley in A Streetcar Named Desire.

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