9 reasons ‘Cruel Intentions’ and its campy sequels deserve to be gay classics
Hop onto Gay Twitter on any given day and, within minutes, you’ll scroll past a “Ryan Phillippe’s butt in Cruel Intentions made me gay” meme. It’s as inevitable as taxes!
But(t) what is Cruel Intentions’ queer legacy beyond Ryan Phillippe’s finest ass(ets)? The Cruel Intentions extended universe turns out to be as gay as Andy Cohen showing Vice President Kamala Harris “Padam, Padam” in front of Stonewall during NYC Pride Weekend. And, come on, that’s the gayest sentence we’ve ever typed. We’re talking Lesbian sexual awakenings! Baby Amy Adams! Christine freakin’ Baranski!
Cruel Intentions had it all.
The film centers on super-rich step-siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillipe), who both want and hate each other. Kathryn bets Sebastian that he can’t seduce the NYC prep school’s most eligible virgin, Annette (Reese Witherspoon). If Kathryn wins, she gets Sebastian’s 1956 Jaguar XK140; If Sebastian wins, Kathryn will finally let him have sex with her. Either way, someone/something is getting ridden.
There’s also a subplot involving Selma Blair’s dim-bulb Celeste, who Kathryn wants revenge on for stealing her summer boyfriend. Sebastian wins the bet, becomes a good person, falls in love with Annette, and—*spoiler alert!*—dies. Kathryn is dethroned when her dirty deeds are exposed to the entire school. Just another day on the Upper East Side.
(It must be noted that there are many dated, problematic elements of 1999’s Cruel Intentions, including blatant homophobia, revenge porn, and various versions of sexual misconduct. Celebrating this film for its queer bona fides does not mean we ignore those very-’90s plot points which simply do not fly in 2023.)
With the recent announcement of the cast of the Cruel Intentions TV series on Amazon, we took a deep dive into everything that makes the world of Cruel Intentions part of the queer canon.
1. Ryan Phillippe: More Than A Butt
Phillippe’s performance as Sebastian Valmont is a gay dream. Or nightmare.
He starts the movie as a petty b*tch who lives for drama (and sex). As the movie progresses, he slowly becomes a sweetie pie, thanks to Annette’s boring yet good influence. We love him. We hate him. We want him. We think we can fix him.
And, though it’s already been discussed, we can’t overstate how formative Ryan’s butt was to literal generations of queer—and the world at large. One could argue that this is… the most important butt ever? The height of *sses in pop culture? The answers are: yes and yes. When ranking the most important peaches in the history of the world, it goes Princess Peach, the Rockford Peaches, and Ryan Phillippe’s cheeks (honorable mention to the desecrated peach of Call Me By Your Name).
The power of this scene, which launched a thousand sexually confusing and confirming erections, knows no bounds. Phillippe’s co-star Sarah Michelle Gellar (see below) even used it as the physical backdrop for her 45th birthday party. Now this is art.
2. Two Words: Christine Baranski
Before she was Tanya, Mary Sunshine, Diane Lockhart, or Agnes Van Rhijn (but, notably, after she was Maryann Thorpe and Connie), and way, way, way before she invented “Gay Rights,” Christine Baranski was Bunny Caldwell in Cruel Intentions.
As Selma Blair’s overprotective (and racist) mother, Baranski gives us a strong blueprint for the type of Upper East Side wealthy white woman we’d come to love to hate, a la The Real Housewives Of New York City. (We would give anything to see Bunny Caldwell on Scary Island throwing a Pinot Grigio at Ramona Singer!)
3. The Source Material: Dangerous Liaisons
Technically, the source material for the entire Cruel Intentions extended universe is the French epistolary novel Les Liaisons Dangereuses, originally published in 1782. But, really, it’s the Academy Award-winning 1988 film, Dangerous Liaisons. And what a queer classic it is!
Glenn Close, John Malkovich, and Michelle Pfeiffer originate the Gellar, Phillipe, and Witherspoon roles and are excellent, over the top, and so, so sexy. Everything from the costumes to the score to the cast, which included fresh-faced Keanu Reeves and Uma Thurman, is perfection.
The real queer bonafides come from the dastardly relationship between Glenn Close and John Malkovich, and their glee in getting petty revenge on those who have wronged them. In that dynamic is every gay friendship that has turned sour over a family meal schedule at Fire Island, a mistaken cocktail order at low tea, or a lost invite to a particularly rousing after-hours orgy.
Adding to the queer legacy is the eternal debate over Glenn Close’s Oscar trajectory. Our official stance is that Glenn should have won her Academy Award 15 years ago for the final scene alone.
4. Sarah Michelle Gellar Can Say F**
Well, in fact, she does!
It was the ‘90s and a different time. Much of the era-specific homophobia in Cruel Intentions comes from Manchester Prep’s queen bee, Kathryn Merteuil. Kathryn ran so Pitzi Pyle could run.
And, by 1999, Sarah Michelle Gellar was a full-on ally on her way to becoming a capital-M Mother. She was already Buffy, everyone’s favorite Vampire Slayer (sorry, Van Helsing), Croaker Queen Helen Shivers in I Know What You Did Last Summer, and ill-fated Cici in Scream 2. And that was before she was Fred’s beard Daphne in Scooby-Doo!
Even without SMG, Kathryn is an absolute legend. She’s one of those high school mean girls queers either were friends with, wanted to be, or were themselves. Kathryn’s lewks were iconic—from her big sun hat and glasses to her cocaine-filled crucifix.
All in all, Kathryn’s most queer-accessible moment is her iconic line: “You can put it anywhere.” It’s always nice to see oneself represented on the big screen.
5. The Campy Sequels
We’ve been alluding to the Cruel Intentions extended universe–because there are not one, but two (!!!) direct-to-video sequels. Cruel Intentions 3 (2004) is connected to the Cruel Intentions movies tangentially by centering on *eye roll* Kathryn’s cousin Cassidy. The film is borderline unwatchable, although valiant effort for casting queer icon Kerr Smith, who played one of primetime TV’s first gay characters, Jack, on Dawson’s Creek. That’s all it has going for it.
Cruel Intentions 2, however, should be galvanized as a camp classic. It was originally conceived as a TV pilot for a prequel series to the original film (Messy production background? Spill that tea, hennnnnny!). The series was scrapped, so the pilot and first episode—along with some R-rated content—were repackaged as a direct-to-video prequel film. It’s a complete mess!
We get a backstory for Sebastian Valmont that makes no sense: He’s an everyman? Who is nice to the staff? And also, he’s poor? With zero sexual charisma and no mean streak? Also, he’s definitely not played Ryan Phillippe. It’s so off-base that it’s somehow completely perfect. This movie also has Mimi Rogers—the original ex-Mrs. Tom Cruise—seductively stroking a pussy cat, sound effects which include a gong and winking noise, and, of course, a baby Amy Adams in the Kathryn Merteuil role (more on her later). It was absolutely terrible, and we can’t recommend it highly enough.
6. An Iconic Soundtrack
Ask four people the most iconic song from Cruel Intentions, and you’ll get four different answers: Is it “Colorblind” by Counting Crows? “Lovefool” by The Cardigans? “Bittersweet Symphony” by The Verve? “Praise You” by Fatboy Slim? Each can make a case for itself.
“Colorblind” gets a big bump for being the score to one of the film’s most iconic moments. The scene once again involves Ryan Phillippe—this time fully clothed (boo!)—atop an escalator, arguably the gayest form of stairs. “Lovefool”’s proximity to William Shakespeare’s Romeo + Juliet will go a long way towards legend status. And “Praise You” is so d*mn ‘90s; you must consider it.
For our money, “Bittersweet Symphony” comes out on top. It punctuates the film’s end in an instantly memorable way. Kathryn gets her comeuppance when Sebastian’s journal exposes her evil ways, which has been photocopied for the entire school. The combination of journal writing, public shaming, and the aforementioned cocaine crucifix is simply too delicious.
7. The Kiss
It’s wild to think that we’ve gone this far without “The Kiss.” If we discuss Ryan Phillippe’s bare butt as a sexual awakening for queer men, we have a moral imperative to raise a glass to the wettest kiss in film history and what it meant to budding queer women.
It’s the scene where Sarah Michelle Gellar’s Kathryn teaches her unsuspecting prey, naive Cecile Caldwell, how to French kiss. In an informal poll (we texted six of our lesbian friends), it was clear that this was a watershed moment for many WLWs (Women Loving Women): “It was like the moon landing. Massively impactful. People who normally wouldn’t watch that type of movie heard about it and went to see it just for the kiss.”
The scene creating a life-long friendship between Selma Blair and Sarah Michelle Gellar doesn’t hurt either.
8. Baby Amy Adams
As mentioned above, one of the best (worst? campiest?) elements of Cruel Intentions 2 is the casting of a pre-fame Amy Adams in the Sarah Michelle Gellar role of this prequel series-turned-film.
It’s ludicrous that she was cast. You know how sometimes you see a soon-to-be star in a small part and think, “Ahh! Of course, this person becomes a star!” Think Julia Roberts in Steel Magnolias, Julianne Moore in The Fugitive, or Channing Tatum in Step Up. Or Amy Adams in her Oscar-nominated breakthrough Junebug.
But, baby, Amy Adams playing a bad girl in Cruel Intentions is not it. And that’s what makes it such a goddamn delight. When she delivers lines like, “I mean, she shops at the Gap!,” or runs a meeting for a secret society at her prestigious prep school, it’s equal parts unconvincing and mesmerizing. Again, we can’t stress enough: Run, don’t walk to Cruel Intentions 2.
9. A Queerty-Approved Cast
We’ve already mentioned the biggies: Baranski. Phillippe. Gellar. Adams. That’s just the tip, so to speak.
Swoosie Kurtz cameos as Sebastian’s therapist in the first film’s opening scene, a call back to her role in 1988’s Dangerous Liaisons. She plays Tara Reid’s mother. Let that sink in. And Reid is giving us everything—she’s basically the “screaming, crying, throwing up” meme in one scene.
Selma Blair’s Cecile is another legend. She’s a virgin who gets dick-matized by Sebastian, and we’ve never related to anyone on screen more.
Oscar-winner Louise Fletcher plays Phillippe’s aunt, a nice nod to her starring role as the grandmother from hell in the incest thriller Flowers In The Attic. And, of course, the role of Annette helped Reese Witherspoon get Legally Blonde, so homage must be paid.
Joshua Jackson is the real MVP of supporting roles. Hot from his turn as Pacey on Dawson Creek, Jackson plays borderline-offensive but all-around delightful Blaine, a demonic twink with bleach-blonde hair (he must be going through it). Blaine is an icon because he has an ongoing clandestine affair with a “straight” bro (Ugly Betty’s boss Eric Mabius; bonus gay points) who “has a mouth like a hoover.” We’ve all been there.
All three Cruel Intentions films are currently available to rent via AppleTV, GooglePlay, Prime Video, Vudu, and YouTube TV.
