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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 ...

    • (117)
    • Roger Kumble
    • R
    • Sarah Michelle Gellar
  4. Return to Manchester Prep for CRUEL INTENTIONS' 20th Anniversary - in theaters March 22 for ONE WEEK ONLY.

    • 2 min
    • 3.3M
    • Sony Pictures Entertainment
  5. Jan 1, 1999 · Watch the 1999 movie Cruel Intentions, a modern adaptation of the novel Les Liaisons Dangereuses, on Internet Archive. Sebastian and Kathryn, two wealthy and manipulative teens, make a bet to seduce Annette, the headmaster's daughter.

  6. 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.

  7. Watch the official trailer of Cruel Intentions, a movie about two wealthy and manipulative step-siblings who bet on seducing two virginal girls. The film stars Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon and Selma Blair.