How Ryan Phillippe’s Ass Made a Generation Queer

But the enduring queer legacy of ‘Cruel Intentions’ is about more than just those perfect cheeks

It was plump and ripe. Best of all, it was forbidden. 

The fruit in question is Ryan Phillippe’s juicy peach in Cruel Intentions. Prudish good girl Annette Hargrove (Reese Witherspoon) walks in on an intentionally nude Sebastian Valmont (Ryan Phillippe) changing into his bathing suit for a night swim. He stands there, drying his ’90s ramen noodle with a white towel while his buoyant butt glistens in the pool lights. It protrudes so perfectly from his slender back. It is a cliff, anchored by a pair of strong, smooth thighs.

As the film’s turning point, Annette develops an appetite for the ass she’ll later bite into. It’s safe to assume Witherspoon’s tantalized reaction was only partly acting: The two co-stars dated while filming and married later that year. (Though they divorced in 2007, they seemingly maintain a positive relationship as parents to Ava and Deacon Phillippe.) 

Phillippe’s ass is onscreen for only two seconds, but it’s lived on in the minds of countless gay men.

Sohail Akhavein, from Minneapolis, was in eighth grade in 2000 when he lost his Cruel Intentions virginity. Akhavein was sleeping over at his friend Brandon’s house after soccer practice. The two feverous Buffy the Vampire Slayer fans rented the film on VHS for their queen Sarah Michelle Gellar, who plays Sebastian’s tempestuous stepsister Kathryn Merteuil. “A minxy busty Buffy who traded a maroon trench jacket for a corset and affinity for the dramatics? Sign us up,” Akhavein recalls. 

Suddenly, while sucking down a Capri Sun Pacific Cooler, Akhavein saw his first “full white moon” that evening. “It was just there: BUTT,” he tells me. The gold-iron pool railings, the art deco glass doors, the “absurd amount of Jumanji fog” filing up the pool room: The set design spoke to his queer Persian heart. “That butt was placed there to tell me that it’s okay to lust and desire after the male bum, even if just for a moment,” he says. 

The film’s queer legacy is riding on more than a plump butt. Cruel Intentions is an equal-opportunity provider, offering a sensational kiss between Kathryn (Gellar) and her protégée Cecile Caldwell (Selma Blair). Picnicking in Central Park, Kathryn teaches Cecile about getting to first base, plopping her mauve-colored lips on Cecile’s. 

Writer Trish Bendix was in ninth grade in Kalamazoo, Michigan, when she saw the film on a rented Blockbuster VHS tape. “As a queer person who didn’t know I was queer yet, the kiss was something I remember feeling like I could get in trouble [for watching],” she tells me. 

The spit-heavy kiss is part of a sinister plotline in which Kathryn manipulates Cecile to get revenge for stealing her lover, Court Reynolds (Charlie O’Connell). “It’s such a moment queer people will always remember, even though there wasn’t anything super-romantic about it,” Bendix.

The scene was later spoofed in Not Another Teen Movie by Mia Kirshner and Beverly Polcyn. Kirshner then went on to play Jenny Schecter, one of the most divisive characters on The L Word. “There’s this continuing queer connection for me from Cruel Intentions,” Bendix says. 

Over the years, Cruel Intentions grew to cult classic status as a melodramatic pre–Gossip Girl depiction of sexual, reckless Upper East Side teens. It helped that watching the film today is like going through a Rolodex of ’90s icons, including Joshua Jackson (Dawson’s Creek), Tara Reid (American Pie) and Eric Mabius (Ugly Betty).

However, sexually voracious teens brooding around grandiose lawns in the Hamptons does not make Cruel Intentions camp, a title retroactively bestowed upon the film. “There’s sometimes a reflex to designate stuff that’s older or dated as camp because the aesthetic is unfamiliar to us,” Kyle Turner, film contributor to Paste magazine, tells me. “But I don’t think that’s a useful conflation.”

Turner, who reluctantly informs me he’s 26, saw Cruel Intentions for the first time a decade after its initial release. It’s one of the movies passed down to younger generations of queer people, predominantly gay men to other gay men, as community tentpoles. 

Josh Harris, a 20-year-old cis gay man, rewatched the movie for the first time in a decade after seeing the final scene (featuring one of his favorite songs, “Bitter Sweet Sympathy” by the Verve) circulate on Twitter. Upon the rewatch, he had a revelation: “The Ryan Phillippe pool scene was my awakening, I’m pretty sure,” he tells me.

Still, the fact of Phillippe’s ass, as well as Christine Baranski and Swoosie Kurtz as high-society Manhattan moms, do not keep the film afloat 21 years later. Sebastian — when not engaging in a pseudo-incestual game of cat-and-mouse with Kathryn — spends the majority of the film forcibly pressuring Annette into sex as part of a bet. “The film doesn’t really connect the dots that Sebastian is a rapist, basically. Manipulation is coercion,” Turner says. Phillippe’s moody status white boy (a prelude to today’s eBoys) does little to make up for the plot holes in a 2020 lens.

Even Akhavein admits it’s hard to achieve the same yearning the film once ignited in him — especially when the retro set design leaves so many questions. “There would never be that much steam. Who is watering those plants? Why is that oversized Pottery Barn blue vase sitting there with nothing in it? Has he ever hidden in it if there are threats of burglars?” he tells me. “Get back to the butt, Sohail.” 

Queer people of a certain age rarely experienced an open high school relationship. Perhaps Cruel Intentions is our first love: It’s uncomfortable, none of it makes sense and you’re better off without it. “It’s quite half-baked and pretty ridiculous,” Akhavein says of the movie. Still, he can “100 percent confirm that one of the pictures I printed out using my parent’s LaserJet ink printer was a still of that white bubble butt.”