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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.

  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.

  3. 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
  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 ...

    • (117)
    • Roger Kumble
    • R
    • Sarah Michelle Gellar
  5. 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. 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
  7. Mar 5, 1999 · A modern-day adaptation of "Dangerous Liaisons" with rich kids in a prep school playing amoral games of seduction and betrayal. The film is smart and merciless until the end, when it becomes soppy and moralistic.