Cruel Intentions Character: Annette Hargrove Year: 1999 Release Date March 5, 1999 Directed By: Roger Kumble Screenwriter: Choderlos de Laclos (novel), Roger Kumble Genre: Comedy, Comedy, Drama, Romance MPAA Rating: R Cast Highlights: ...Ryan Phillippe ...Sarah Michelle Gellar ...Selma Blair Filming Locations: Los Angeles, California, USA New York City, New York, USA Toronto, Ontario, Canada + more

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Mean and rich step siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) and popular students at their school take a bet that will change everybody’s lives forever. The new headmaster’s daughter, Annette (Reese Witherspoon), is a virgin whom wishes to wait until marriage. When Sebastian, a proud serial womanizer learns of this, he takes a bet with his step sister that he will take her virginity before the new school year begins. If he looses, she gets to have his cherished Jaguar but if Sebastian succeeds, he gets to have the one thing he’s always wanted yet never been able to have - Kathryn. A series of events follow that leave Sebastian questioning his quest for Annette, a romance blossoms, Kathryn seethes with jealousy, a drug scandal is discovered, dark secrets are revealed and a life is lost forever.

• Marks Reese and Ryan Phillippe's only movie that they've made together. • Reese originally turned down her role, but later went for it after Ryan and the director convinced her to. • Out of all of the roles she has played, Reese wishes she was most like Annette. "I think she has a very strong sense of self that I admire."

• “Because I don’t trust myself with you." • “It's not all about winning, Sebastian.” • “Its okay you can laugh, I promise I won't tell anyone.”

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