Screenwriter and director Roger Kumble wrote the script for the 1999 movie Cruel Intentions in just 12 days while on a trip to Mexico, after mulling over the idea for a little over a year.
“It was one of those moments when you’re just walking across the street,” he told Cosmopolitan in 2014. “The idea popped into my head to do Dangerous Liaisons set in high school.”
The seductive teen dramedy about spoilt Manhattan rich kids, starring Ryan Phillippe, Sarah Michelle Gellar and Reese Witherspoon, was a hit, grossing $113 million worldwide on a $15.8 million budget.
It has become a cult classic that still resonates 25 years on, with a killer soundtrack, memorable moments, and a reboot TV series in the works for Amazon Prime.
“It was daring and edgy, and some people were against the movie and didn’t think it was a good idea,” Gellar recalled to Entertainment Tonight in 2019.
“I think we always knew that we were doing something really cool.”
The scandalous story of bored, vicious queen bee Kathryn (Gellar) who bets her stepbrother Sebastian (Phillippe) that he can’t seduce the headmaster’s sweet daughter (Witherspoon) catapulted its stars into the spotlight.
“It was so naughty and so funny, but also such a classic, even if it’s not politically correct,” co-star Selma Blair told Entertainment Weekly in 2019.
“It’s a story that endures, and people do still act that way. They just don’t want people to know about it.”
For the talented, up-and-coming cast, the Cruel Intentions film set was also the place where some of their most significant relationships blossomed.
When he signed on, Phillippe had been quietly dating a young Witherspoon, who beat out the studio’s pick of Katie Holmes to play the wholesome, innocent character Annette.
But it took some convincing – and a few drinks! – on the director’s part to get Witherspoon on board.
“So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk,” Kumble told Cosmopolitan in 2014. “And I literally got down on my knees and begged her.
“And Reese was like, ‘I’ll do it. But we need to work on the character.’ I’m like, ‘Anything, anything, anything.’ She wanted to strengthen the character, and she was right.”
Making the film together only cemented Phillippe and Witherspoon’s love and, three months after the premiere, the pair were married.
Soon after, their daughter Ava, now 24, arrived, and then son Deacon, now 20, but the Hollywood marriage only lasted seven years before they announced their divorce.
Still, the former couple look back fondly on that time in their lives, even sharing anecdotes with their children when they were older.
“We got to meet up as a family and took a walk through Central Park with the kids, and it was funny – we were reminiscing then because we shot a lot of Cruel Intentions [there], so there we were with Ava and Deacon talking, and they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” Phillippe recalled in 2014.
Another lifelong friendship that began on the New York set was Blair and Gellar’s, with the pair only meeting shortly before they filmed that iconic kissing scene.
“I think I knew from the first moment I met Sarah Michelle Gellar that we would be friends forever,” Blair told Self magazine in 2023. “And she’s made sure that’s happened.”
The women have remained close over the years, with Gellar acting as a pillar of support for Blair ever since her 2018 multiple sclerosis diagnosis.
“She’s amazing … I think she’s tougher than I ever thought,” Gellar says.
Where are the cruel intentions cast now?
Reese Witherspoon
Witherspoon’s career has gone from strength to strength, with hit films such as Legally Blonde, Sweet Home Alabama, Wild and Walk the Line, for which she won an Oscar for Best Actress in 2006. Witherspoon also runs mega-successful production company, Hello Sunshine, and currently stars on TV’s Morning Wars.
Ryan Phillippe
The actor went on to star in Company Man, Crash, Breach, MacGruber, The Lincoln Lawyer, Brothers by Blood and One Shot. In 2014, he wrote and directed his first movie, Catch Hell, and he’ll next be seen in series Motorheads.
Sarah Michelle Gellar
In recent years, the actress has been on hiatus, prioritising family life with husband, Freddie Prinze Jr. and kids Charlotte, 14, and Rocky, 11. She went back to work in Netflix’s 2022 teen comedy Do Revenge and series Wolf Pack.
Selma Blair
Blair starred with Witherspoon again in Legally Blonde and appeared in The Sweetest Thing and the Hellboy franchise. Blair, who has son Arthur, 12, also played Kris Jenner on American Crime Story: The People v. O.J. Simpson.
Joshua Jackson
Post Cruel Intentions, the Dawson’s Creek star found great TV success on The Affair, Dr. Death and Fatal Attraction. He dated Diane Kruger for 10 years until 2016, then wed and had a daughter with Jodie Turner-Smith. They split in October.
Where to watch Cruel Intentions in Australia
Stream Cruel Intentions on Prime Video from $9.99/mth, with a 30-day free trial. Subscribe Now.
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