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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 streaming: where to watch online? Currently you are able to watch "Cruel Intentions" streaming on Freevee for free with ads or buy it as download on Apple TV, Amazon Video, Vudu, Google Play Movies, YouTube, Microsoft Store, Redbox.

    • Roger Kumble
    • R
    • 25
  3. Cruel Intentions. Sarah Michelle Geller, Ryan Phillippe and Reese Witherspoon star in this steamy, stylish look at Manhattan's posh youth and their wanton games of sexual manipulation. IMDb 6.8 1 h 37 min 1999. R. Drama · Romance · Alienated · Cerebral. This video is currently unavailable. to watch in your location. Details. More info.

  4. Cruel Intentions. 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. 5,655 IMDb 6.8 1 h 37 min 1999. X-Ray R.

    • 97 min
  5. 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 a pair of unscrupulous siblings...

  6. 'Cruel Intentions' is currently available to rent, purchase, or stream via subscription on Amazon Video, Apple iTunes, Vudu, Google Play Movies, Redbox, IMDB TV Amazon Channel, YouTube, and...

  7. Cruel Intentions: Directed by Roger Kumble. With Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair. 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.