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
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