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Cruel Intentions (1999) - Also known as "Cruel Inventions"

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, Alaina Reed-Hall, Deborah Offner, Tara Reid, Herta Ware, Hiep Thi Le, Charlie O'Connell, Fred Norris, Ginger Williams

Synopsis

Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
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