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Cruel Intentions   1999         R, 97 min. Genre: Drama / Romance / Thriller Director: Roger Kumble   Cast: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Louise Fletcher, Joshua Jackson, Eric Mabius, Sean Patrick Thomas, Swoosie Kurtz, Christine Baranski   Rather shallow characters—Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe)—attending an affluent prep school appear to control the social life in their small world. The plot for this film revolves around a bet that Sebastian will be able to bed the new headmaster's virgin daughter, Annette Hargrove (Reese Witherspoon).

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