Trivia / Cruel Intentions

  • Actor Allusion: Sebastian hands Kathryn a magazine that has Jennifer Love Hewitt on the cover. Both Ryan Phillippe and Sarah Michelle Gellar had starred alongside her in I Know What You Did Last Summer.
  • Dawson Casting: Ryan Phillippe was twenty-five, Reese Witherspoon twenty-three, Sarah Michelle Gellar twenty-two and Sean Patrick Thomas was nearly thirty. Selma Blair, meant to be a freshman, was the oldest of the actors playing the teens.
  • Method Acting: When Annette slaps Sebastian in the face during their breakup scene, the slap wasn't supposed to happen. Both Ryan Phillippe and Reese Witherspoon became caught up in the intensity of the scene that she impulsively slapped him. Sebastian's look of shock was genuine and Ryan even threw up after the scene was finished filming.
  • Old Shame: Cruel Intentions 2 is this for Amy Adams, though she does poke fun at it.
  • The Other Darrin:
    • In Cruel Intentions 2, Ryan Phillippe's and Sarah Michelle Gellar's roles were recast with Robin Dunne, king of the direct-to-video sequels, and an up-and-coming Amy Adams, respectively.
    • In the TV series reboot, Reese Witherspoon's character has been recast with similar-looking actress Kate Levering.
  • Playing Against Type:
    • Buffy Summers plays Kathryn. Unless you knew her as Kendall first, in which case it's returning to type.
    • Pacey Witter from Dawson's Creek playing Camp Gay Blaine.
    • Amy Adams is now best known for doe-eyed cutie roles.
  • Romance on the Set: Ryan Phillippe and Reese Witherspoon were dating and got married for seven years.
  • So My Kids Can Watch: An odd variation, given the film's subject matter. But Christine Baranski signed on because her kids were huge Buffy fans and were ecstatic at the thought of their mother working with Sarah Michelle Gellar.
  • What Could Have Been:
    • The original ending, in script form, can be viewed here.
    • The title was going to be 'Cruel Inventions', but it was changed because it sounded too much like the title of a sci-fi movie.
    • The studio were lobbying hard for Katie Holmes to play the role of Annette, but Roger Kumble didn't think she had the strength of character for the role.
    • A scene was filmed showing Sebastian hitting Kathryn. The filmmakers deleted it to suggest that Kathryn could have been lying when she tells Ronald that Sebastian hit her.
    • Cruel Intentions 2 was originally conceived as a spin-off TV series, but ended up getting released as a direct-to-video sequel.

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