MisMatched

Actor: SARAH MICHELLE GELLAR

Film: "Cruel Intentions"

Character: Kathyrn

Year: 1999

That lifeless face, that whiny monotone voice... just a couple of things that help prove how bad Sarah Michelle Gellar was in 1999's soap-opera-esque "Cruel Intentions". Gellar played Kathryn, a spoiled, overly sexualized, slightly-evil, rich girl who bets her hot stepbrother Sebastian (miscast with a cheesy Ryan Phillippe) that he can't bed the new girl in school. Of course he takes the challenge and falls in love with Annette (played by Reese Witherspoon)... blah blah blah. Gellar is painfully bad and extremely annoying to watch.

*this is where Reese and Ryan met.

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