12 Things You Didn’t Know About Cruel Intentions

  
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10. The Studio Wanted Katie Holmes to Play Annette

The studio initially wanted Katie Holmes for the Annette part, but director Roger Kumble thought the role “needed someone with a little more strength of character.” Phillippe was already signed on to the part of Sebastian, so Kumble became interested in hiring his girlfriend at the time, Witherspoon. “So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk,” Kumble said. “And I literally got down on my knees and begged her: ‘Please, it’ll be 15 days, you’ll be great.’ And Reese was like, ‘I’ll do it. But we need to work on the character.’ I’m like, ‘Anything, anything, anything.’” Together they strengthened Annette’s character, so that she wasn’t such a “doormat.”

Photo: Andrew Eccles / ©Sony Pictures / Courtesy Everett Collection

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9. Inspired by a Book

Cruel Intentions was inspired by the movie Welcome to the Dollhouse. The director Roger Kumble had recently seen it and felt as though he hadn’t seen such a dark high school flick. “I’d just seen Todd Solondz’s Welcome to the Dollhouse, and I was like, Wow … f–ked up high school. Never seen this. It was so dark. And it was one of those moments when you’re just walking across the street, and the idea popped into my head to do Dangerous Liaisons set in high school. And I mulled it over for a year,” Krumble said. “Then I put a play up in 1997 called d girl and I got David Schwimmer to be in it, at the height of Friends. And that was a game-changer for me. It was a pretty dark play. It was about a screenwriter who’s just looking to seduce this innocent d-girl [short for development girl, a person in film production who scouts potential movie ideas]. I put that up and it was a hit out in LA. So I had some heat, and I didn’t want to lose it. Literally, the day the play went down I went to Mexico and I wrote Cruel Intentions in 12 days.”

Everett Collection

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