Trivia / Cruel Intentions

• Creator Backlash: Amy Adams sometimes pokes fun at Cruel Intentions 2.
• 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. This one at least was intentional according to Word of God; as the character has a sex scene with Sebastian, all auditionees were asked their age.
• Deleted Role: Alisha Klass, noted porn star, had a scene as a cheerleader that was cut. She can be glimpsed when Sebastian is talking to Annette on the phone.
• Follow the Leader: Following the trend started by Clueless of 'high school version of classic literature' in the 90s. Word of God is that it was heavily inspired by Welcome to the Dollhouse as well.
• Method Acting: When Annette slaps Sebastian in the face during their breakup scene, the slap wasn't supposed to happen. Ryan Phillippe and Reese Witherspoon, who were a real-life couple at the time, became caught up in the intensity of the scene that she impulsively slapped him. Sebastian's look of shock was genuine and Ryan even went outside and threw up after the scene was finished filming because the emotions had been so intense.
• 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:
  • Sarah Michelle Gellar, best known as Buffy Summers, plays Kathryn. Unless you knew her as Kendall first, in which case it's returning to type.
  • Joshua Jackson from Dawson's Creek playing Camp Gay Blaine.
  • Amy Adams is now best known for doe-eyed cutie roles, making this a retroactive example.
• Production Posse: Producer Neal H Moritz had worked with both Ryan Phillippe and Sarah Michelle Gellar in I Know What You Did Last Summer.
• Romance on the Set: During the movie, Ryan Phillippe and Reese Witherspoon were dating. The couple got married three months after the movie's release and had two children together, but ended up divorcing in 2008.
• 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.
• Technology Marches On: Invoked when Cecile and Ronald send letters to each other and when Ronald suggests emailing Cecile, Sebastian responds that "emails are for geeks and pedophiles".
• Throw It In!: During their kissing scene, Sarah Michelle Gellar and Selma Blair were not meant to produce the spittle, but after someone on-set noticed, they had to do the scene again. Cinematographer Theo van de Sande proclaimed it was "beautiful".
• What Could Have Been:
  • Sebastian originally had a Villainous Breakdown when Kathryn refuses to sleep with him even after he dumps Annette, going into a tearful, psychotic tirade and even hitting Kathryn. However, it was cut out because it lessened the feeling that Sebastian could truly be redeemed. Interestingly, Kathryn still tells Ronald that Sebastian hit her, making it seem like a lie when it was originally meant to be true. Fortunately, it's completely in-character for her to tell a lie such as this.
  • One version of Roger Kumble's screenplay had an ending where Annette, instead of publishing the journal and crushing Kathryn, keeps it to herself and announces her cruel intentions to play games on Kathryn under the threat of revealing the contents. The original ending, in script form, can be viewed here.
  • 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.
  • Cruel Intentions 2 was originally conceived as a spin-off TV series called Manchester Prep, but ended up getting released as a direct-to-video sequel.
  • The sex scene was eventually scored to "Colorblind" by Counting Crows. Roger Kumble wanted the Smashing Pumpkins' song "To Sheila" for it, but singer and guitarist Billy Corgan turned them down.
• Working Title: 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.

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