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  1. 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.

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

  3. Mar 4, 2019 · 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...

  4. Mar 5, 1999 · Advertisement. The film stars Ryan Phillippe, a slinky schemer in the tradition of James Spader, as Sebastian Valmont, a rich kid who lives in a Manhattan mansion with his stepsister Kathryn Merteuil ( Sarah Michelle Gellar ).

  5. Official Trailer. 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. The pawns? The naïve Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon).

  6. Cruel Intentions - Movies on Google Play. 1999 • 97 minutes. 4.5 star. 169 reviews. 54% Tomatometer. Rating. family_home. Eligible. info. play_arrow Trailer. info Watch in a web browser or on...

  7. About this movie. arrow_forward. Sarah Michelle Gellar (I Know What You Did Last Summer, Scream 2, TV's Buffy The Vampire Slayer) and Ryan Phillippe (I Know What You Did Last Summer, 54) sizzle as...

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