Reese Witherspoon In Cruel Intentions Flashback ( Photo Credit – Prime Video )
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Reese Witherspoon may have dazzled as the sweet and composed Annette in Cruel Intentions, but her road to the role wasn’t paved with studio deals or script admiration. Instead, it took a tipsy dinner, some desperate charm, and a director literally dropping to his knees. Back in the late ’90s, filmmaker Roger Kumble found himself stuck between studio pressure and his personal pick for the film’s leading lady. What followed wasn’t a typical casting process — unless your idea of negotiations includes alcohol, boyfriend leverage, and on-the-spot rewrites. Keep reading, because this behind-the-scenes story is a scene in itself.
How the Director Landed His Leading Lady in Cruel Intentions
In 1999, director Roger Kumble was gearing up for his first feature, Cruel Intentions. With the pressure to lock in the perfect cast, one key role was left dangling — Annette, the story’s moral anchor.
“We got into disagreements over who was going to play Annette. The studio wanted Katie Holmes, who was just starting to do Dawson’s Creek. And I liked this actor, Vinessa Shaw,” he told Cosmopolitan. “And we just couldn’t agree.”
With casting talks going nowhere fast, Kumble turned to his film’s leading man for some off-the-record advice. Ryan Phillippe, already cast as Sebastian, was dating Witherspoon then, and the director saw an opening. “I was hanging out with Ryan one night and I was like, ‘What about your girlfriend?’”
not only did the new director for awc work on cruel intentions; but reese witherspoon and ryan phillippe ended up getting married and having kids. we eatin GOOD pic.twitter.com/dshZFC7QwI
She wasn’t an easy sell, already booked and busy, she needed more than flattery to say yes. Trying to win her over, Kumble and Phillippe took Witherspoon out for dinner. But things didn’t go as planned. “We took Reese out to dinner to get her drunk, and we ended up getting drunk. And I literally got down on my knees and begged her, ‘Please, it’ll be 15 days, you’ll be great!’”
Witherspoon agreed with a condition. “I’ll do it. But we need to work on the character.” Kumble replied, “Anything, anything, anything!”
Even after agreeing to the part, Witherspoon didn’t take it at face value. She pushed for script changes, determined to make Annette feel authentic and layered—not just a passive presence in the storyline. “She wasn’t a doormat,” Kumble recalled, crediting her for transforming the character into someone far more nuanced and impactful. Looking back, her creative input clearly paid off.
