If you’re a gay man who came of age in the late ’90s, chances are there’s one particular scene permanently etched into your memory: Ryan Phillippe dropping his towel by the pool in Cruel Intentions.
That perfect posterior, captured for just two glorious seconds of screen time, sparked more sexual awakenings than perhaps any other moment in ’90s cinema.
Ironically, the same actor who unintentionally ignited these revelations had already made LGBTQ+ history years earlier as Billy Douglas, television’s first gay teenager on One Life to Live.
And guess what? Ryan knows exactly what that revealing moment did to us.
What Was Cruel Intentions, Anyway?
For those who need a refresher, Cruel Intentions was the deliciously wicked teen drama that took the classic novel Les Liaisons Dangereuses and reimagined it with privileged Manhattan teens.
The 1999 film starred Phillippe as the manipulative Sebastian Valmont, alongside Sarah Michelle Gellar, Reese Witherspoon, and Joshua Jackson.
Speaking of Joshua, his portrayal of Blaine Tuttle was another groundbreaking aspect of the film. Mostly known from Dawson’s Creek at that point, Jackson stepped into the role of a gay character who defied the stereotypes of the era.
“I was more concerned with making my character real,” Jackson shared a few years ago. “You didn’t see a lot of gay characters, period. But [especially] gay characters that weren’t caricatures, so I wanted to make sure that, even with dialogue that was beautifully over-the-top, he still felt like a real person.”
The film became an instant cult classic, particularly among LGBTQ+ audiences who found themselves drawn to both Phillippe’s physical attributes and the memorable same-sex kiss between Gellar and Selma Blair.
It’s interesting to note that Amazon recently tried to reboot the film – as a TV series on Prime Video – but the show got cancelled after just one season.
The Scene That Changed Lives
In a reunion interview with Entertainment Weekly a few years ago, Phillippe addressed his infamous poolside nude scene with characteristic good humor: “I felt okay with [showing] my butt. Everybody has a butt, it’s really not that graphic,” he said, before dropping the kicker:
“So many guys on Twitter are like, ‘That’s the moment I knew I was gay,’ and there have been guys like, ‘I behaved like Sebastian to get laid!'”
Not everybody has assets like THAT, Ryan.
- Watch Cruel Intentions on Amazon’s Prime Video (US)
- Watch Cruel Intentions on Amazon’s Prime Video (UK)
Before The Fame: Billy Douglas Breaks Ground
What many don’t realize is that Phillippe’s connection to the LGBTQ+ community goes far deeper than just being an unintentional gay icon.
Years before Cruel Intentions had guys rewinding their VHS tapes to that pool scene, a teenage Ryan was making actual television history.
In 1992, at just 17 years old, Phillippe portrayed Billy Douglas on the daytime soap One Life to Live – the first gay teenager ever to appear on American television.
This wasn’t just a milestone; it was revolutionary, especially considering it happened when gay representation was nearly non-existent on screen (at least in the US).
“I remember the fan mail that we would get, my mother and I would get, from gay teenagers or from parents of gay teenagers who found a way in to relate to or talk to their child through the show,” Phillippe told TooFab in a 2017 interview.
The impact of Billy Douglas went far beyond entertainment. “One kid said he’d considered ending his life before seeing a character like him being accepted,” Phillippe revealed.
“I also heard from a father, a mechanic, who hadn’t spoken to his son since he came out. When our show came on in his shop, it gave him some insight and understanding as to who his son was, so it opened up communication between them.”
Pretty profound stuff for a teenage soap actor in the early ’90s.
Not Always Smooth Sailing
Taking on the role came at a personal cost. Phillippe, who had grown up attending Baptist and Christian schools, faced backlash from his religious community.
“I was shunned at that point,” he admitted. “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.”
A few years later, Phillippe would further explore queer characters with a role in the film 54 (or Studio 54), where he played a bisexual character alongside Mike Myers and Breckin Meyer.
Though his character’s bisexuality and a kiss scene with Meyer were initially cut from the theatrical release, they were later restored in the Director’s Cut.
“We did something that was relatively bold for two young male actors, and we took pride in the places that the original story went,” Phillippe said about finally having the scene restored.
The Legacy Lives On
From making television history as Billy Douglas to creating an iconic movie moment that helped countless young men embrace their sexuality, Ryan Phillippe has inadvertently become a significant figure in LGBTQ+ pop culture history.
So whether you first discovered him as the groundbreaking Billy Douglas, or whether your sexual awakening came courtesy of that perfectly sculpted physique in Cruel Intentions, one thing is clear: Ryan Phillippe deserves a special place in the pantheon of straight allies who’ve made an unexpected but lasting impact on gay culture.
And that famous poolside scene? Well, it’s secured its place in gay cinema history forever.
- Watch Cruel Intentions on Amazon’s Prime Video (US)
- Watch Cruel Intentions on Amazon’s Prime Video (UK)