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Jerkass Woobie / The Sopranos

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Almost all the main cast qualify at one point or another, but Tony and especially Paulie exemplify this. However, as the series progresses, their shadier actions start to outweigh their sympathetic qualities. Even Bobby Baccala proves from time to time that even if it isn't his normal personality, he can put on a very frightening persona. Ask a union rep who crossed Junior at one point.

  • Uncle Jr, especially in the final season.
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  • Vito. He's a slimy, maneuvering worm, but some part of you just wants him to stay in New Hampshire and marry Nice Guy Johnnycakes.
  • Adriana. Almost a Butt-Monkey, but you'd have to be a cold bastard not to feel some sympathy for her...or a member of the mob.
    • To wit: her relationship with Christopher is gradually ruined by the former's drug habit, which itself leads to sexual impotence and the death of her dog, and when Adriana revealed to him that she was an FBI informant, she is brutally strangled and then killed.
  • Christopher can sometimes fall here when he isn't a complete psycho. For example, when he was being bullied by the two Tonys.
  • Carmela. Most of the time (due to Tony’s philandering, among other reasons), but particularly in Season 5, where she’s separated from Tony and constantly blamed, berated, and generally pushed to the breaking point by an adolescent and abusive A.J.
  • Bobby Baccala. Nobody else compares. Father killed off one season, his wife the next. And then he married Janice. Poor bastard. And then Tony goads him into punching Tony in the mouth. Then Tony forces Bobby (who is not Ax-Crazy like his comrades) to commit a murder as a punishment.
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