Twenty years after its debut, Cruel Intentions still has a massive fan base and is credited with helping several viewers, famously including Demi Lovato, realize they were queer.
However, the teen romance film was rated R back when it came out in 1999, and star Ryan Phillippe wasn't sure his parents would love the movie as much as fans did.
Ryan chatted with Barstool Sports' KFC Radio on Tuesday, Nov. 17, and revealed that he was worried his parents would disown him after his role in Cruel Intentions.
He was asked if the storyline, about two teens making a sex bet, felt "normal" at the time. Ryan responded, "No, and you know, I thought my parents were going to disown me."
The Crash actor, who was 23 when he made the film, explained that it wasn't the first time his parents had disapproved of his work.
He had grown up attending a religious school but went on to portray revolutionary LGBTQ characters onscreen. "My first role ever, though, coming out of the Christian school when I was a senior in high school, I played the first gay character on a soap opera, first gay teenager ever," Ryan continued.
He noted that from then on, in the eyes of his family and community, "I was shunned at that point. So they were already out of the picture... They weren't happy about it."
Ryan later recounted exactly how he landed the role of Sebastian Valmont opposite Sarah Michelle Gellar's character Kathryn Merteuil. The story began on the set of I Know What You Did Last Summer, when a producer handed him the script for Cruel Intentions. "I read the script in my trailer," Ryan dished. "[The producer was] like, 'I want you to take a look at the script, it's kind of like risqué or whatever.'"
The star feels like he's never played a part quite like the mischievous teen in the years since. According to Ryan, "It was just so fun to be so flippant... The emotions are theatrical."
Ryan went on to marry his co-star Reese Witherspoon in June 1999, just three months after their film came out. The pair, who officially split in 2008, share two lookalike kids: 21-year-old Ava Phillippe and 17-year-old Deacon Phillippe.
More recently, Ryan appeared in the 2020 TV series Big Sky and will soon be seen in the film Lady of the Manor.
He's still nothing but proud of how pop culture fans have continued to rally around Cruel Intentions over the years, and even acknowledged that there was going to be a Cruel Intentions TV show a few years ago, but it didn't end up airing on NBC. "This movie somehow finds new fans all the time," he said.