A loose adaptation of Choderlos De Laclos' 1782 novel Les Liaissons Dangereuses (which has been filmed three times before), Cruel Intentions revamps the story by moving it to the United States in the late 1990's and revising the context from royal romantic intrigue to teenage trechery among the filthy rich. Sarah Michelle Geller plays Kathryn, a beautiful but cold-hearted and manipulative young woman who enjoys making wagers with her jaded step-brother Sebastian (Ryan Phillippe). When Kathryn's boyfriend breaks off with her because he's infatuated with the less worldly Cecile (Selma Blair), Kathryn challenges Sebastian to seduce Cecile in order to ruin her new love. Sebastian reluctantly agrees, but is far more intrigued with a newer challenge -- Annette (Reese Witherspoon), the daughter of his private school's headmaster, who is intelligent, beautiful and has appeared in "Seventeen" magazine proudly announcing she intends to remain a virgin until the day she's married. Katheryn and Sebastian make a new bet: if he can bed Annette before the end of summer vacation, Katheryn will spend a debauched evening with him, but if he fails, she'll take ownership of his prized 1956 Jaguar. Supporting cast includes Swoozie Kurtz, who has gone this route before, having appeared in Stephen Frears' period adaptation of this story, Dangerous Liasons.