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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. 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.

  4. 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 ...

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  5. 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...

  6. 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.

  7. This darkly comedic adaptation of DANGEROUS LIAISONS stars Sarah Michelle Gellar and Ryan Phillippe as wealthy and emotionally ruthless teenagers who place...

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