Cruel Intentions (1999)

Have you ever made a bet that changes your life? Sebastian Valmont (Ryan Phillippe) is offered a wager by Kathryn Merteuil (Sarah Michelle Gellar), his step-sister, that he cannot bed the virginal daughter of their private high school’s new headmaster, Annette Hargrove (Reese Witherspoon). If Sebastian fails to lure Annette into bed before the summer is over, Kathryn gets his prized car. If he succeeds, Sebastian gets Kathryn. Little do they realize that Annette is made of stronger stuff than either realize.

Director:  Roger Kumble Writer:  Choderlos de Laclos; Roger Kumble Cast:
Sarah Michelle Gellar -  Kathryn Merteuil Ryan Phillippe -  Sebastian Valmont Reese Witherspoon -  Annette Hargrove Selma Blair -  Cecile Caldwell Louise Fletcher -  Helen Rosemond Joshua Jackson -  Blaine Tuttle Eric Mabius -  Greg McConnell Sean Patrick Thomas -  Ronald Clifford		Swoosie Kurtz -  Dr. Regina Greenbaum Christine Baranski -  Bunny Caldwell Alaina Reed Hall -  Nurse Deborah Offner -  Mrs. Michalak Tara Reid -  Marci Greenbaum Herta Ware -  Mrs. Sugarman Hiep Thi Le -  Mai-Lee Charlie O’Connell -  Court Reynolds