‘Cruel Intentions’ star Ryan Philippe chatted with Barstool Sports‘ KFC Radio on Tuesday, November 17, and revealed that he was worried his parents would “disown him” because he made the movie.
Cruel Intentions was released in 1999 and has become a cult classic. The controversial film is about prep school teens making a sex pact. There is even a sexual dynamic between Phillippe’s character “Sebastian” and his stepsister Katheryn, played by Sarah Michelle Gellar. When asked if making the movie felt “normal,” he replied, “No, and you know, I thought my parents were going to disown me.”
The actor and ex-husband of Reese Witherspoon shared that his early work went against everything he was taught in Christian school. Per DailyMail, Phillippe was still attending New Castle Baptist Academy in Delaware when he became the first gay teenager on a daytime soap opera. In 1992 he began playing the role of Billy Douglas on “One Life To Live.” He celebrated his 18th birthday that same year.
“So like 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 and so I was shunned at that point. So they were already out of the picture,‘” he explained. ‘I mean this was 1992, and I was playing a gay teenager and I was in a Christian school. They weren’t...they weren’t happy about it, but so when I was doing the  movie I Know What You Did Last Summer the same producer had the script for Cruel Intentions and I read the script in my trailer during the shoot.” Phillippe’s continued, “we were near the end of shooting I Know What You Did Last Summer and he’s like: “I want you to take a look at the script.” He’s like, ‘It’s kinda, you know, it’s a little risky’ - risque or whatever.” He’s like, ‘But take a look at it.”’ Phillippe’s couldn’t believe what he was reading and recalled, “But I was like, I remember walking out the trailer and finding him. I’m like, ‘Are you guys really going to make this?”’
Phillippe went on to make the film and starred opposite his real-life girlfriend Witherspoon. The actor said he has “never played a character like that since” but would love to play a character like Sebastian again. He is also proud that it‘s “held up” for 20 years. “It was just so fun to be so flippant and sort of, you know, theatrical... It’s cool that it holds up, man. You know, a lot of times you take a movie from a specific point in time that’s supposed to connect with a younger crowd and it just stays. This movie somehow finds new fans all the time. You know, they were going to do a series about Cruel Intentions, a TV series a year or so ago. There’s like a musical out there that’s really good actually. They put it back in theaters for its 20th anniversary. That only happens with like The Godfather,” Phillippe said proudly.
Phillippe and Reese got married in June 1999, three months after the film was released. They divorced in 2008 and share two lookalikes: 21-year-old Ava Phillippe and 17-year-old Deacon Phillippe. Phillippe shared a series of photos on Instagram from a recent hiking trip he took with Deacon to Joshua Tree National Park in California. The picture showed the father-son duo posing for selfies, climbing rocks, and showing off their blasters. He captioned the post, “Free Duo.”
Fans couldn’t help but notice their striking resemblance and called them twins. Fans also noticed that he’s barely aged. One commented, “Alright Ryan, we have teenagers now. That means you need to age with the rest of us. Not fair!!”