‘Cruel Intentions’—and Cinema’s Most Important Butt—Turn 25

Even the Marcia fucking Brady of the Upper East Side gets gray hair.

At least that’s what I’m saying to comfort myself upon learning that Cruel Intentions, one of the rare instances of an absolutely perfect film—keep your rosebud, Orson Welles—turned 25 this week. Celebrating this quarter-century milestone might be an occasion to feel unfathomably old—unless of course, like me, you weren’t even born yet when the film originally came out. Ha! I’m so young! Definitely wasn’t of a formative age such that this movie, its performances, delectable dialogue, and one monumental set of butt cheeks imprinted on me forever! Nope, no sir!

Does it help matters that the beholder of that aforementioned luscious rump that shaped the libidos (and, for a certain subset—hi!) sexualities of a generation still looks like this at age 49? Well, it’s at the very least inspiring. After seeing those photos, I may take the weekend to refurbish the clothing rack in my bedroom back into its intended form as an exercise bike.

Anniversaries of beloved films breed a kaleidoscope of emotions, a blurred collage of nostalgia, wistfulness, joy, and some notes of bitterness; it’s a cruel world in which a piece of art attached to such vibrant, fond memories has aged to the point it reminds us of how old we’ve gotten. That’s certainly the case with Cruel Intentions. It can’t be possible that Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair opened that film 25 years ago. But the occasion of its birthday—congrats on being able to rent a car!—is apt for exploring what it was about the campy teen psychosexual drama that pierced the zeitgeist like a lightning bolt in 1999, with a jolt that’s kept its fans charged for the two-and-a-half decades since.

Cruel Intentions was a reimagining of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses, set at a fancy high school attended by Manhattan’s richest and most privileged—a concept so bizarre that it was either a stroke of a genius or an indication that a development exec was having a stroke. (Obviously, the creative gamble paid off.)

Sarah Michelle Gellar was Kathryn, the school’s social chess master who used everyone in her orbit as pawns in devious schemes that were often meant to hurt, and typically for no reason other than her own amusement. Ryan Phillippe was her stepbrother Sebastian, a dreamboat who earned his reputation as a cad, and whose desire to bang the “only person he can’t have”—his stepsister—is the catalyst for Kathryn’s tangled web of plotting.

Kathryn wants Sebastian to seduce cartoonishly naive incoming freshman Cecile (Selma Blair), a deflowering that would appall Cecile’s mother (Christine Baranski, a key casting in elevating Cruel Intentions to gay iconography) and exact revenge on Kathryn’s ex, Court (Charlie O’Connell), who is now dating Cecile. Sebastian is on his own sex-motivated mission, though: The school’s new headmaster’s daughter, Annette (Reese Witherspoon), published an essay in Seventeen about the virtue of teens saving themselves for marriage, and he wants to rebut her piousness by getting her to sleep with him. Save for his stepsister, it’s the ultimate conquest.

For the younger set, the film’s acid-tongued, frank talk about sex and relationships presented a danger-tinged fantasy version of what being a grown-up—i.e. a high schooler who looks a twenty-something Hollywood celebrity—might be like: a little scary, but an edgy thrill. For the target set the same age or slightly older than the characters, the film had a hilarious, smutty filter that exaggerated what were otherwise relatable concerns about social politics, self-consciousness, betrayal, and different, warring moral compasses that are a very real part of the high school experience. And for everyone else, including the audience that aged with the film—now sharing a demographic with the characters’ parents—the film was and is alternately shocking, salacious, ridiculous, and just plain fun.

Behold Ryan Phillippe Gazing at a Painting of His ButtMASTERPIECE

Fletcher Peters, Kevin Fallon

The film only works because of its perfect cast, one of the finest examples in modern movie history where a roster of “It” actors assembled at the exact time their Hollywood quotient was skyrocketing. Writer-director Richard Kumble’s dialogue drips with Shakespearean snark that’s only as delicious as it is because the cast played the humor with surprising humanity. Each character is a familiar high-school archetype—the mean girl, the dreamy player, the goody two-shoes—but the central trio of Gellar, Phillippe, and Witherspoon mine impressive, riveting depth from them, to the point that the movie almost graduates from being utterly silly to serious.

Also, they’re all so hot.

So, let’s talk about the butt, because you can’t talk about Cruel Intentions without talking about the quick flash of Ryan Phillippe’s butt in the pool scene. I feel sheepish being so crass and objectifying, but this isn’t just a butt. Twenty-five years later, it is pop-culture canon, woven into the fabric of our very culture. It is such an important butt.

The scene is both entirely gratuitous and the single most necessary and consequential frame in cinematic history. Watching it is akin to seeing color for the first time, discovering what it means to feel, or learning how to breathe. Gay men of a certain (my) age talk with each other and post on social media constantly about how the scene was an a-ha moment in their sexual awakenings, and have for 25 years. Do you know how perfect an ass has to be for that to be the case?

But the bum is just one ingredient in creating Cruel Intentions’ indelible legacy. There’s the performances, the soapiness, the devastating use of The Verve’s “Bitter Sweet Symphony,” the spitty same-sex French kiss, the unapologetic acknowledgement that teens have sex and do drugs, and the whole weird sort-of incest vibes.

I’d rather roll naked down a hill littered with pinecones and poison ivy than reignite the Saltburn discourse, but there was something to the film’s blackmailing and erstwhile naughtiness that managed to be both winking and sophisticated, which I think audiences missed in Saltburn. It understands the trauma of growing up, and how we manipulate how others see us because we’re so afraid of how we see ourselves. It has the romance of young love and young sex—both the optimism of it and the doomed nature of it—all while being absolutely outrageous.

The film has lasted for all of those reasons. And also Ryan Phillippe’s butt.