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Cruel Intentions

IMDb: 6.8
Drama (1999, USA)

Roger Kumble's teen re-telling of `Dangerous Liaisons' featuring handsome and rich Sebastian Valmont and his step-sister Katherine. He can have any girl at school, except Annette Hargrove, a paragon of virtue, and of course Katherine, who decides to make a bet with him to seduce Annette. If he fails, Katherine gets his sports car and if he succeeds, he can sleep with her as well. Directed by: Roger Kumble.

Sarah Gellar Kathryn Merteuil
Ryan Phillippe Sebastian Valmont
Reese Witherspoon Annette Hargrove
Selma Blair Cecile Caldwell
Louise Fletcher Helen Rosemond