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  1. Cruel Intentions: Directed by Roger Kumble. With Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair. 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.

  2. The naïve Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon). Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire by making a diabolical wager of sexual conquest without consequences. The pawns?

    • 2 min
  3. Sarah Michelle Gellar (I Know What You Did Last Summer, Scream 2, TV's Buffy The Vampire Slayer) and Ryan Phillippe (I Know What You Did Last Summer, 54) sizzle as a pair of unscrupulous siblings in a deliciously sexy tale of seduction, revenge and conquest. After cleverly seducing and ruining the reputation of an unsuspecting classmate (Selma Blair, Can't Hardly Wait, Zoe, Duncan, Jack & Jane ...

  4. Mar 5, 1999 · Teenagers once went to the movies to see adults making love. Now adults go to the movies to see teenagers making love. "Cruel Intentions'' is a modern-day version of "Dangerous Liaisons,'' with rich kids in a prep school playing roles that were written for jaded French aristocrats in the wicked 1782 novel by Choderlos De Laclos. He created a world of depraved amorality, in which the only goal ...

  5. Cruel Intentions. Based on the novel Dangerous Liaisons, this dark nostalgic cult classic, starring Sarah Michelle Gellar, Ryan Phillippe and Reese Witherspoon. Elitist, manipulative siblings Sebastian and Kathryn are out to get what they truly desire. Enter Annette - the Headmaster's daughter, innocent and virtuous - a perfect new conquest for ...

  6. Cruel Intentions (1999) cast and crew credits, including actors, actresses, directors, writers and more.