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  1. Cruel Intentions is a 1999 American teen romantic drama film written and directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses, set in New York City among rich high schoolers.

  2. Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences.

  3. Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian's (Ryan Phillippe) and Kathryn's (Sarah Michelle Gellar) deliciously diabolical wager of sexual conquest when she writes an ...

  4. Jan 1, 1999 · Sebastian tries to seduce Annette, his headmaster's virgin daughter, to win a bet with his step-sister Kathryn. She wants his costly car while he wants a night with her. But Annette has other plans.

  5. Mar 5, 1999 · Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn.

  6. Drama. arrow_forward. 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...

  7. Mar 5, 1999 · "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.

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