Ryan Phillippe Thought His Parents Would "Disown" Him After This Movie
Sarah Oconnell
Updated on February 22, 2026
If you were a kid or a teen when the future cult classic Cruel Intentions came out in 1999, your parents probably weren't too eager for you to see it. The drama, a modern version of Les Liaisons dangereuses, is plenty scandalous, especially for 20 years ago. Even one of the stars of the film was concerned about how his family would feel about its debaucherous teen characters and sexy storyline. In fact, in a new interview with Barstool's KFC Radio podcast (via Us Weekly), Ryan Phillippe revealed that he thought his parents might "disown" him for playing Sebastian Valmont in Cruel Intentions.
Keep reading to find out what the actor, who stars in the new ABC drama Big Sky, had to say about this enduringly controversial role. And for more adolescent classics, check out The Best Teen Movie That Came Out the Year You Graduated.
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Phillippe's parents had already "shunned" him for another role.
In the early '90s, long before he was offered Cruel Intentions, the actor played a character named Billy Douglas on the soap opera One Life to Live—one of the first main gay characters on daytime TV. Through Billy, the show tackled issues including prejudice and the stigma around AIDS, but Phillippe's family and community weren't thrilled about his first major role.
"I had grown up going to, like, Baptist school and Christian school," Phillippe explained on the podcast. "When I was a senior in high school, I played the first gay character on a soap opera—first gay teenager ever—and so I was shunned at that point. I mean this was 1992, and I was playing a gay teenager and I was in a Christian school. They weren't happy about it."
For more actors who had their big break on daytime, check out 40 Stars Who Started Out on Soap Operas.
His first reaction to the Cruel Intentions script was "Are you guys really going to make this?"
Phillippe was given the script for Cruel Intentions while he was shooting the 1997 slasher movie I Know What You Did Last Summer. A producer on the horror movie was set to produce the steamy drama too. "I remember walking out the trailer and finding him," Phillippe said of reading the raunchy screenplay. "I'm like, 'Are you guys really going to make this?' And he said, 'Yeah.'"
Though he was 23 years old when Cruel Intentions filmed, the actor still worried that it would upset his family further. "I thought my parents were going to disown me," he said.
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Here's why the movie was so controversial.
Cruel Intentions centers on a pair of step-siblings played by Phillippe and Sarah Michelle Gellar, who are beautiful, rich, and bored. Sebastian and Kathryn (Gellar) treat the people around them like toys, especially when it comes to sex. When they learn that their prep school headmaster's daughter (Reese Witherspoon) has written an essay about abstinence for a teen magazine, they bet each other that Sebastian can't seduce her. Knowing that her stepbrother is attracted to her, Kathryn agrees to be the prize if he's successful. Suffice it to say that the film earns its R rating both through dialogue and love scenes, even though it ends with a message of true love conquering all.
To see where it ranks among the rest, check out Ranking Every '90s Teen Movie, From Worst Reviewed to Best.
But Phillippe doesn't regret doing the movie.
The actor didn't elaborate on how his parents took the news, nor did he say whether or not they'd even seen the film. Regardless, it seems that he doesn't have any regrets about doing it—and not just because he got to work closely with his now-ex Witherspoon, who he wed the year their movie came out.
"I've still never played a character like that since. I want to get back to playing a character like Sebastian in Cruel Intentions," Phillippe said. "It was just so fun to be so flippant and sort of like, you know, the emotions are theatrical."
"It's cool that it holds up," he added. "This movie somehow finds new fans all the time."
To see what some of the other hottest actors of that decade are up to in 2020, check out The Biggest '90s TV Teen Idols, Then and Now.
Sage Young Sage Young is the Deputy Entertainment Editor at Best Life, expanding and honing our coverage in this vertical by managing a team of industry-obsessed writers.Read moreFiled UnderCelebrities • EntertainmentRead This NextStars Who Turned Down "Dancing With the Stars"
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