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Cruel Intentions Director “Begged” Reese Witherspoon to Join Cast, Katie Holmes Lost Role

Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar
Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar starred in the wildly popular 1999 drama, Cruel Intentions.

Colorblind was almost colorless! The 1999 movie, Cruel Intentions, would not have been as memorable without a young Reese Witherspoon, who was “begged” to play the virtuous character of Annette Hargrove, according to screenwriter/director Roger Kumble.

“We got into disagreements over who was going to play Annette,” Kumble told Cosmopolitan on Monday, Aug. 18. “The studio wanted Katie Holmes, who was just starting to do Dawson’s Creek. And I liked this actor Vinessa Shaw. And they were both great. But this was early Katie, and I thought we needed someone with a little more strength of character. And we just couldn’t agree. And then, literally, I was hanging out with Ryan [Phillippe] one night and I was like, ‘What about your girlfriend?'”

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(In the late ’90s, I Know What You Did Last Summer hunk Phillippe and Witherspoon emerged as one of young Hollywood’s hottest couples, alongside Sarah Michelle Gellar and Freddie Prinze Jr. The Cruel Intentions costars got married in June 1999, three months after the smash drama’s release, when Witherspoon was six-months pregnant with their daughter Ava. They later welcomed their second child, Deacon, in 2003, only to separate in 2006.)

“So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk,” Kumble recalled to Cosmo. “And I literally got down on my knees and begged her: ‘Please, it’ll be 15 days, you’ll be great.'”

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Witherspoon, 38, who was in her early 20s at the time, agreed to play the role of Annette with one stipulation. “Reese was like, ‘I’ll do it. But we need to work on the character,'” Kumble said. “I’m like, ‘Anything, anything, anything.’ She wanted to strengthen the character, and she was right. And she and I got together, and we gave Annette more bite so she wasn’t a doormat. And I’m very grateful to her for that.”

reese witherspoon in cruel intentions
Cruel Intentions director Roger Kumble “begged” Reese Witherspoon to play Annette, a role which almost went to Katie Holmes.

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Kumble also recalled Witherspoon and Phillippe’s famous sex scene, which was memorably set to the tune of the Counting Crows’ “Colorblind.”

“There were two scenes where I kind of gave them their space and made the set as comfortable as possible,” Kumble revealed. “The lovemaking scene — in any situation like that, you shut the set down — and the breakup scene.” Of the latter scene, the director reiterated how Phillippe threw up while shooting it.

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reese witherspoon and ryan Phillippe in cruel intentions
“We ended up getting drunk and I literally got down on my knees and begged her,” Cruel Intentions director Roger Kumble said of Reese Witherspoon.

“I think Ryan talks about it often — he threw up on set,” Kumble said. “And it was one of those things where I just let the cameras roll. ‘Let’s go back, do it again, let’s go back.’ I want to be professional, but until I feel like we have it, you just have to go. As a director, you’re like, ‘I’m not going to be the most liked person today.’ I don’t think we did too many takes. But, you know, you get what you need to get. You really want to see him ripping his heart out.”

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