Cruel Intentions is a 1999 feature film starring Sarah Michelle Gellar, Ryan Phillippe, Selma Blair, and Reese Witherspoon. It was based on the 18th century French novel Les Liaisons Dangereuses, but unlike other modern film versions of the novel (such as Dangerous Liaisons and Valmont), Cruel Intentions was set in the present and played with teenagers. The film was released on March 5, 1999.

The plot concerns a bet made between Kathryn Merteuil (played by Gellar) and her stepbrother Sebastian Valmont (played by Phillippe). Sebastian must seduce Annette Hargrove (played by Witherspoon), a virgin and the daughter of the principal of the private school that the three attend. Courtesy of http://en.wikipedia.org/wiki/ Cruel_Intentions