Katie Holmes Almost Played Reese Witherspoon's Role in ‘Cruel Intentions’

Reese Witherspoon was the perfect actor to play Annette Hargrove in the ‘90s teen cult classic Cruel Intentions. Acting opposite her then-boyfriend (and future husband) Ryan Phillippe, Witherspoon embodied Annette, a principled young woman who is seduced by Phillippe’s scheming Sebastian Valmont character. But if studio executives had had their way, Witherspoon may never have been in the movie. Originally, they wanted Katie Holmes to play the Annette role. 

‘Dawson’s Creek’ star Katie Holmes was almost cast in ‘Cruel Intentions’ 

Katie Holmes was a rising star in the last ‘90s. She got her big break on the hit teen drama Dawson’s Creek and also starred in the movies Disturbing Behavior, Go, and Teaching Mrs. Tingle. So, when producers were looking for someone to play Annette, Holmes seemed like an obvious candidate. 

But not everyone was on board with the idea of casting Holmes, including Cruel Intentions’ writer-director Roger Kumble.

“We got into disagreements over who was going to play Annette,” Kumble told Cosmopolitan in 2014. “The studio wanted Katie Holmes, who was just starting to do Dawson’s Creek. And I liked this actor Vinessa Shaw.” (Shaw had a supporting role in Hocus Pocus and later went on to appear in Ray Donovan, 3:10 to Yuma, and other shows and movies.)  

According to Kumble, both Shaw and Holmes were “great.” But he wasn’t sure the actor known for playing Joey Potter was the right fit for Annette.

“[T]his was early Katie, and I thought we needed someone with a little more strength of character,” he said. “And we just couldn’t agree.”

Reese Witherspoon was dating Ryan Phillippe, but that wasn’t why she was cast 

Kumble’s quest for the perfect Annette eventually led him to Witherspoon. At the time, she was dating Phillippe, who had already been cast as Sebastian. 

“And then, literally, I was hanging out with Ryan one night and I was like, ‘What about your girlfriend?’” Kumble recalled. However, as he later explained to Entertainment Weekly in the magazine’s oral history of the movie, the fact that she was dating Phillippe wasn’t why she was cast. “We knew how talented Reese was,” he said. “He just happened to be going out with her at the time.”

Kumble approached Witherspoon about the movie, but she was hesitant to sign on. 

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

As Witherspoon recalled to Entertainment Weekly, getting her to say yes required “a lot of coercing.” But she finally agreed, on one condition. She wanted to make some changes to Annette’s character “so she wasn’t a doormat,” according to Kumble. He agreed, and she accepted the role. 

Katie Holmes’ ‘Dawson’s Creek’ co-star Joshua Jackson was in ‘Cruel Intentions’ 

While Holmes ultimately wasn’t cast in Cruel Intentions, one of her Dawson’s Creek co-stars was in the movie. Joshua Jackson — who played Pacey Witter on the WB series — portrayed Sebastian’s friend Blaine Tuttle. Blaine sleeps with Annette’s closeted gay ex-boyfriend, who is then blackmailed by Sebastian. 

Jackson told Entertainment Weekly that he relished the chance to play a role so different from the ones he was normally offered. 

“Teenage roles were written very two-dimensionally: You were the jock or the nerd or the hot one,” he recalled. “I was a precocious 19- or 20-year-old who expected roles to be intelligent and stupid and bad and funny and over-the-top. [This] elevated the material.”

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