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Title: Cruel Intentions
Year: 1999
Rating: 6.801
Cast: Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, Selma Blair, Louise Fletcher
Description: 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.