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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, set in New York City among rich high schoolers, is a modern retelling of Pierre Choderlos de Laclos ' 1782 novel Les Liaisons dangereuses .

  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. Mar 4, 2019 · 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. Cruel Intentions. 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.

  6. 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.

  7. Mar 5, 1999 · Watch Sarah Michelle Gellar and Ryan Phillippe as unscrupulous siblings who bet on ruining the reputation of a classmate and seducing his virgin sister. See reviews, cast, trailer and more on Movies Anywhere.