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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 ...

    • (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. Are you in, or are you out? #Cruel20 Get tix: http...

    • 2 min
    • 3.2M
    • Sony Pictures Entertainment
  5. Watch the trailer of the 1999 drama romance film about two wealthy, manipulative step-siblings who make a wager of sexual conquest. The film stars Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon and Selma Blair.

  6. 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.

  7. Cruel Intentions Trailer 1999Director: Roger KumbleStarring: Louise Fletcher, Reese Witherspoon, Sarah Michelle Geller, Ryan Phillippe, Selma Blair, Sarah Mi...

    • 2 min
    • 2.6M
    • Video Detective
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