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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. Summaries. 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. Kathryn Merteuil and Sebastian Valmont are seductive, manipulative step-siblings who get what they want when they want it.

  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 article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend.

  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 ...

    • Drama
  5. 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.

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

  7. Mar 4, 2019 · Return to Manchester Prep for CRUEL INTENTIONS' 20th Anniversary - in theaters March 22 for ONE WEEK ONLY.

  8. 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.

  9. Mar 5, 2024 · Cruel Intentions,” the 1999 teen drama which celebrates its 25th anniversary this week, tells the story of spiteful stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont ...

  10. 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.

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