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Cruel Intentions
1999 · 1 hr 37 mins
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
Cast: Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, Selma Blair, Louise Fletcher