re: Characters who were not exactly villains, but you found them to be despicable.

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Toby from the Office is the epitome of the theme of this thread

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No. Toby is who Michael makes out as the villain but you really halfway root for him because of how bad he's treated.

I got so pissed the first and only time I saw “the notebook”. The lead leaves her fiancé and it is supposed to be this great thing. I’ve always found that whole thing to be trashy.

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Sharon Stone in Casino

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Maybe, but Roth was 100% calculating business realistic. He knew exactly what she was. So much so, that when he proposed she straight up told him she didn't love him and he said it didn't matter, the feelings will come. He knew what the deal was, it was his idea, and he was an idiot to try to control it. You can't just HIRE a spoiled whore as a trophy wife, give her zero affection, and expect her to play the role dutifully.

Rose in titanic
Henry VIII in Tudors

Also Elaine is dating a guy named Joel Rifkin and she wants him to change his name because its the same as a serial killer.

She proposes the name OJ. The episode aired a year before the murders in Brentwood.

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You can't just HIRE a spoiled whore as a trophy wife, give her zero affection, and expect her to play the role dutifully.

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Agree except for no affection part.

Corporal Upham - From the movie Saving Private Ryan:

This guy...this freaking guy!! He was directly responsible for so many American deaths, all because he wanted to "play by the rules" during WAR!! His little Nazi buddy that he saved, ends up coming back to kill many of the real soldiers...just like Reiben said he would. Mellish's death was absolutely brutal (slow knife stabbing), as Upham cried like a baby on the steps feeling sorry for himself instead of helping Mellish. Upham crying on the steps also led directly to Sergeant Horvath's death, because he had to pull Upham off the steps and ends up being mortally wounded because of the chain of events. I hate his charachter with every fiber of my being. He was so pathetic, he even wrote a book about the bonds of brotherhood during war...before the actual war!! He thought he was so cultured for speaking German "With a hint of Bavarian"...and yet i love it how the real soldiers kept the "German" word "FUBAR" a secret from him. Entitled little prick!! It sucks that only Reiben, Ryan and Upham survive. He didn't deserve to live.

Rhonda in the Wire always annoyed me.
Obligatory AJ Soprano.
The daughter in Friday Night Lights.

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Janice Soprano

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I think she's a villain.

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But…she also gave Gump his first and only taste of pussy. No other woman on the planet did that.

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A lady that tasted like cigarettes tried