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.
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 upcoming TV series reboot, Reese Witherspoon's character has been recast with similar-looking actress Kate Levering.
Playing Against Type: Both of Kathryn's actresses. Sarah Michelle Gellar was known either as an Action Girl or else a wholesome character in some way. 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.