Kathryn Merteuil (played by Sarah Michelle Gellar) is the most popular girl in her upper class, snobby high school. Her step-brother Sebastian Valmont (played by Ryan Phillippe) has a reputation that would do Wilt Chamberlain proud, as he has been able to have any woman he wants. Every woman, that is, except his step-sister, who toys with him mercilessly. After reading a "Why I'm going to wait"-magazine article by Annette Hargrove (played by Reese Witherspoon), a new transfer to his school, Sebastian determines that she will be his greatest conquest. Certain that this will not be the case, Kathryn suggests a wager: if Sebastian is able to sleep with Annette, he can have Kathryn any way he wants her. However, if he fails, Kathryn takes ownership of Sebastian's beloved car.
1999's Cruel Intentions is probably the best transformation of an erotic French novel into a teen movie ever. When the sultry Kathryn Merteuil sets out to destroy the virginal Cecile Caldwell (played by Selma Blair), all hell breaks loose. Merteuil's weapon in this dastardly deed is her stepbrother Sebastian Valmont, who has his own conquest in mind. The two make a wager - if Sebastian can't corrupt his obsession, the prim Annette Hargrove, Kathryn gets his beloved Jaguar. But if he wins, he gets to sleep with his stepsister. Of course, this is all a larger plot by the vicious Kathryn, who orchestrates events until everybody but her loses.
"Life's a bitch, but so is she..."