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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. 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.

    • Roger Kumble
    • 2 min
  3. Mar 5, 2019 · Sarah Michelle Gellar’s crucifix necklace with a twist, Reese Witherspoon goofing around in a convertible classic car, the kiss that was a sexual awakening for an entire generation of queer...

  4. Phillippe was dating Reese Witherspoon at the time, and both Kumble and Phillippe convinced Witherspoon to star as Annette Hargrove. Witherspoon signed on under one condition: the character...

  5. Mar 21, 2019 · The filmmakers and cast members — including Ryan Phillippe, Selma Blair, Joshua Jackson, and more — reflect on Roger Kumble's hit.

  6. Mar 25, 2019 · Les Liaisons Dangereuses, the 18th-century French novel that inspired Cruel Intentions, ends unhappily for all its players, but filmmaker Roger Kumble didn't want to wrap up his take with a...

  7. Mar 5, 1999 · Agreed, says Sebastian, but soon he finds a greater challenge--the virginal Annette (Reese Witherspoon), daughter of the new headmaster at their expensive school. She's written an article for Seventeen magazine praising premarital virginity, and Sebastian bets Kathryn he can deflower her.

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