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Reese Witherspoon didn’t want to star in Cruel Intentions, and for good reason

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Kayleigh Dray
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Reese Witherspoon and Sarah Michelle Gellar in a scene from the film 'Cruel Intentions', 1999. (Photo by Columbia Pictures/Getty Images)

“I remember finding Annette too demure and too much of a woman influenced by a guy’s manipulations,” says the actress. 

Ready to feel as ancient as the skeletal remains housed inside the Natural History Museum? Then, boy, do we have a bombshell for you: Cruel Intentions just turned 20. Yikes.

To celebrate the 20th anniversary of the dark and sexy dramedy, the cast – Reese Witherspoon, Sarah Michelle Gellar, Selma Blair and Ryan Phillipe – have sat down with Entertainment Weekly to provide their oral history of the film. 

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Just in case you’ve forgotten, the plot of the 1999 teen hit, which was based on the French novel Les Liaisons Dangereuses, sees Sebastian Valmont (Phillipe) enter a bet with his step-sister Kathryn (Gellar) to seduce their headmaster’s daughter, Annette (Witherspoon). 

Of course, Sebastian doesn’t bank on falling in love with her… which is exactly what happens. Go figure.

The movie grossed $75 million (£51million), seven times what it cost to make, and kick-started the career of its stars. However, it seems Witherspoon – who was dating Phillipe when the film was made – initially wasn’t all that happy about joining the cast.

Speaking frankly to EW, Witherspoon said that she was coerced into accepting the role after being taken out to dinner by her then-boyfriend and the filmmakers. 

“I thought we were all just going to dinner as friends, and then Roger [Kumble] and Ryan asked me to do the movie,” she said. “I remember a lot of coercing.”

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Everyone involved in the project remembers Witherspoon being reluctant to take on the part. However, she worked with filmmakers to adjust Annette’s character.

“She came and sat with me for a week, and we worked on the dialogue together,” recalled writer-director Roger Kumble. “Annette was the character most removed from me. There’s no way the movie would have its success if it weren’t for [Reese’s] talent as a writer.”

Witherspoon added: “I remember finding Annette too demure and too much of a woman influenced by a guy’s manipulations.

“I was starting what I guess became my bigger mission in life — of questioning why women were written certain ways on film.”

And what a mission it has been: not only did Witherspoon later bring us the feminist tour de force that is the Legally Blonde franchise (she is currently working on a third Elle Woods movie), but she has also been a key member of the Time’s Up movement, too.

Similarly, Witherspoon has been instrumental behind the success of HBO’s critically-acclaimed Big Little Lies due to launching her own production company, which has resulted in getting films made that feature interesting and complex female characters(think Wild and Gone Girl, to name just two).

But what about Cruel Intentions, eh?

Well, Kumble and Witherspoon worked hard to come up with a version of Annette that that felt palatable to a feminist audience, and the film proved a success. And, more importantly, Witherspoon does not look back on her role with any regrets whatsoever. Indeed, the Legally Blonde actress even thinks that Cruel Intentions could be remade today for modern-day audiences.

“It’s a piece of classic literature about how people manipulate each other,” she said. “I’m sure there could be some new iteration of it with new people. It’s just about somebody who’s imaginative coming up with an idea.”

Image: Getty

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Kayleigh Dray

Kayleigh Dray is editor of Stylist.co.uk, where she chases after rogue apostrophes and specialises in films, comic books, feminism and television. On a weekend, you can usually find her drinking copious amounts of tea and playing boardgames with her friends. 

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