33. Kathryn Merteuil
Played By: Sarah Michelle Gellar
Movie: Cruel Intentions
The only thing worse than a scheming, conniving trick is one who's acting up out of sheer boredom. Rich girl Kathryn Merteuil and her douche of a step-brother Sebastian (Ryan Phillippe) literally have nothing better to do than systematically dismantle the lives of their innocent classmates around them—namely the virginal, pure Cecile (Selma Blair) and Annette (Reese Witherspoon)—and try to bring them down to their narcissistic, warped level.