Cruel Intentions (1999)

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Director:

Roger Kumble

Stars:

Sarah Michelle Gellar (Kathryn Merteuil), Ryan Phillippe (Sébastian Valmont), Reese Witherspoon (Annette Hargrove), Selma Blair (Cecile Caldwell), Louise Fletcher (Helen Rosemond), Joshua Jackson (Blaine Tuttle)