It’s Been 20 Years Since “Cruel Intentions,” And There’s Never Been Another Movie Quite Like It

Back in 1999, when nihilism was cooler than niceness, the shameless teen debauchery of Cruel Intentions sparked a generation’s sexual awakening.

There are a lot of memorable moments in Cruel Intentions, which came out 20 years ago today, in 1999. But I will always remember it for being the first time I saw two girls kissing.

Sarah Michelle Gellar plays Kathryn Merteuil, the delightfully vicious head bitch of an elite Manhattan prep school, who is giving her new protégé, Cecile Caldwell (Selma Blair), some important life lessons. Lounging on a blanket in Central Park, they’re two visual opposites: Sweet, ditzy Cecile wears a preppy uniform of green and pink, complete with a plaid knee-length skirt and a sweater wrapped around her shoulders; Kathryn’s in all-black vintage (skirt suit, round sunglasses, giant floppy hat), as if to spite the bright, beautiful New York summer unfolding around them. Cecile admits she’s untrained in the ways of kissing, and Kathryn admonishes her for never having practiced on her girlfriends. When Kathryn turns Cecile to face her and gives her a quick peck, Cecile is surprised to find how easy and pleasant it is. “This time, I’m gonna stick my tongue in your mouth, and when I do that, I want you to massage my tongue with yours,” Kathryn says, matter-of-fact. “And that’s what first base is.”

The resulting makeout — a closeup of tongues and ’90s-chic brown-lipsticked lips, topped off with an infamous dribble of spit after Kathryn pulls away — has become one of the most famous girl-on-girl kisses in popular film history. Gellar and Blair were awarded Best Kiss at the 2000 MTV Movie Awards, for which Gellar thanked the filmmakers for “being the sick perverts they are.” The kiss was spoofed in a particularly gross, drooly makeout in 2001’s Not Another Teen Movie (featuring Mia Kirshner, who would soon go on to pass first base with plenty of women in The L Word), spurred the sexual awakenings of an untold number of straight men and lesbians, and is still occasionally censored on cable TV.

Watching the scene in my living room when I was 12 or 13, cross-legged on the floor and one foot away from my television, made me suddenly terrified that my mom would walk in on me at any moment and discover the pervy lesbo I secretly was. This was around the time I was watching a lot of Gilmore Girls and 7th Heaven, being slowly indoctrinated by casual conservatism. Cruel Intentions, in its sheer scandalousness, blew my preteen mind.

“It was kind of that movie that you weren’t supposed to let your parents know you’ve seen,” Jordan Ross, the co-creator of Cruel Intentions: The Musical, said in a 2017 interview. “I think a little bit of that was because of how sexy and how naughty it was, and how there was that feeling of ‘If my parents find out I watched this, I’m gonna get in so much trouble.’”

That feeling Cruel Intentions evokes — like you’re doing something a little dirty, a little dangerous, which makes it all the more pleasurable — is perhaps why, 20 years after its release, the film is still such a mainstay in popular culture. (That, and its incredible soundtrack.) The movie, written as a riff on a 1782 French novel that has spawned multiple other adaptations — Pierre Choderlos de Laclos’s Les Liaisons dangereuses — has inspired many spinoffs of its own, from sequels to musicals to a (failed) television series. And this month, Sony is re-releasing the film in theaters to celebrate its anniversary.

The plot of the movie hinges on a bet Kathryn makes with her stepbrother Sebastian Valmont (Ryan Phillippe), who goes to the same Manhattan prep school and is bored by dating unadventurous Manhattan debutantes. She thinks he won’t be able to seduce the supposedly abstinent Annette Hargrove (Reese Witherspoon), the new headmaster’s daughter, before the start of the fall term. If Kathryn wins, she gets Sebastian’s 1956 Jaguar roadster; if Sebastian wins, he gets to “put it anywhere,” as Kathryn says, splayed suggestively on her bed. First-time director Roger Kumble, speaking to Cosmo, remembered that Phillippe told him on set: “When you break down this movie, it’s really about me wanting to have anal sex with my sister.” It’s a dirty movie about delightfully mean teens.

When Cruel Intentions was first released, Gellar said last month in an interview with ET, “We were coming out of a John Hughes era and moving into these sort of frothy, romantic comedies.” The film appealed to her because “to take material like Les Liaisons dangereuses, and give it to teens and that material — it was sort of the first of its kind.”

The only real takeaway seems to be that people are bad, and we’re all gonna die. But you might as well get in a few good one-liners before you do.

Twenty years after its release, Cruel-style Mean Teen movies have again become rather rare, replaced by a rebooted era of Niceness: There are wholesome teen rom-coms (To All the Boys I’ve Loved Before; Love, Simon) and tearjerker dramas about kids with life-ruining illnesses (The Fault in Our Stars; Everything, Everything; Five Feet Apart), including the subgenre Jezebel dubbed “Sad Teen Death Movies.” The current teen rom-com renaissance offers a lot to love — we’re slowly seeing a more diverse group of teens cast in starring roles, certainly more so than in Hughes’ time — although the most recent batch also tends to glamorize some tired tropes of the genre in attempts to critique them. But overall, these movies are nice! And it’s nice to watch nice people win in the end.

I don’t think we necessarily need more movies about filthy rich white teenagers being horrible to each other — television tends to have that area more thoroughly covered these days — but I do think it’s notable that, while a same-sex kiss is not so likely to shock anymore, Cruel Intentions doesn’t look significantly less debaucherous today than it did 20 years ago. Nor is it any less bonkers. We’re ping-ponged between scenes that are sexy and sultry — even sweet — and scenes that depict full-on criminality (sexual assault; revenge porn). You think one character’s using another, but turns out the first guy was the one being used all along. Who’s worthy of redemption here? What are we supposed to take away from all of this? What does it all mean?

Upon a 20th-anniversary rewatch, I think the answer might be: not much! Cruel Intentions’ indulgence of teenage nastiness, as well as teenage obsession and devotion, paints a picture of morality so scrambled that the only real takeaway seems to be that people are bad, and we’re all gonna die. But you might as well get in a few good one-liners before you do, and look fucking fantastic along the way.

Though Cruel Intentions received mixed reviews from critics, it was a commercial hit, grossing $75 million worldwide on a shoestring $10.5 million budget, paving its way toward cult classic status. But the movie was not always destined to be a juggernaut. Kumble, who also wrote the script, thought he was making a modest little indie, he told Cosmopolitan in 2014. But then producer Neal Moritz, fresh off of I Know What You Did Last Summer, took a liking to the project and brought two stars along with him: Gellar and Phillippe. Kumble and Phillippe together begged Phillippe’s then-girlfriend, Witherspoon, to sign on to play Annette. (To do so, Kumble said, “we took Reese out to dinner to get her drunk.” Yikes!)

Kumble, in the Cosmopolitan interview, said that he was inspired to write Cruel Intentions after watching Todd Solondz’s 1996 Welcome to the Dollhouse. “I was like, Wow … fucked up high school. Never seen this. It was so dark.”

As production designer Jon Gary Steele put it in the film’s production notes, “I didn’t want it to feel like a young, bright teen film, because it’s not. It’s very tragic; everyone basically loses.”

Adam White, in a 2017 Telegraph piece about how the film “seduced a generation,” pointed out that “in an era where even the best young adult actors were usually found playing stock roles such as The Bitchy Prom Queen or The Handsome Jock in between their tenures on teen television, Cruel Intentions offered rising stars an opportunity to prove their range.” Gellar, in particular, had reason to sign on, he wrote: “Off the back of a double bill of pretty, helpless murder victims in Scream 2 and I Know What You Did Last Summer, and her two-season role as Buffy Summers, Gellar was given a chance to prove she could be more than a Vampire Slayer or a doomed damsel in distress.”

There's something sort of refreshing about Kathryn’s complete lack of redeeming qualities.

Dying her hair dark to distinguish herself from Buffy, Gellar gave it her all as the abominable Kathryn, someone who feels forced to act prim and prude in polite society while secretly carrying on her real life as a sex maniac and coke fiend.

There’s something sort of refreshing about Kathryn’s complete lack of redeeming qualities. And, unlike Sebastian, she has actual reason to play the two-faced bitch. As she says in the best monologue of the movie, when Sebastian casts doubt on their latest schemes: “Eat me, Sebastian. It’s alright for guys like you and Court to fuck everyone, but when I do it I get dumped for innocent little twits like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady? I’m the Marcia Fucking Brady of the Upper East Side and sometimes, I wanna kill myself.” She’s not nice, but she’s also not wrong.

“We had long talks about her history,” Gellar told Premiere magazine in 1999. “Roger [Kumble] used to always say, ‘Don’t you think that she was abused?’ And I’d say, ‘No, I think she had a perfect upbringing. I think her mother adored her and her father sent her amazing gifts. She just wanted more.”

(Gellar also didn’t think that the film should be dismissed as mere smut. In the same Premiere interview, she addressed Buffy creator Joss Whedon, who’d jokingly demeaned the film at a press conference: “I did what I think is my best work to date in that movie. Brushing it off by calling it ‘a porny’ is unbelievably hurtful to me. He owes me flowers. And that’s on the record.”)

En route to destroying her ex-boyfriend Court, Kathryn will screw over Cecile, just for existing, as well as Cecile’s mother, Bunny (Christine Baranski), for being Cecile’s mother; Cecile’s music teacher, Ronald (Sean Patrick Thomas), for falling in love with Cecile; and, ultimately, her stepbrother Sebastian, for falling in love with someone else.

What muddies Cruel Intentions’ moral waters is that most of the people who get screwed over kind of deserve it; everyone is so hideously flawed that whoever we’re supposed to be rooting for at any given time is never in our favor for long. For example, Kathryn weaponizes Bunny’s racism to push Ronald, who’s been writing love letters to Cecile, out of a job (Bunny: “I got you off the streets and this is how you repay me?!” Ronald: “Got me off the streets? I live at 59th and Park!”). The firing itself seems somewhat justified; Ronald’s seduction of the childish and naive Cecile, while in a position of authority as a teacher, feels bad and gross. “She’s so young,” Kathryn says with fake concern, “and he’s so…” You’re expecting her to finish with “much older,” but Bunny jumps in with “black!” (Later, Ronald will cheat on Cecile with Kathryn, giving him an even lower moral high ground.)

So the single black character in the movie ends up villainized, just as the token couple of gay characters do. Sebastian develops a plan to blackmail Annette’s closeted, football-playing friend Greg (Eric Mabius) — who he thinks has turned Annette against him — by photographing Greg in bed with Sebastian’s friend Blaine (Joshua Jackson, in full bleached-blonde glory). Sebastian and Kathryn both use plenty of anti-gay slurs — “queer,” “fag” — and you’d wonder why a gay guy like Blaine would put up with Sebastian’s shit. But in the end, he’s no victim; he lies about Greg and uses Sebastian’s conniving ways against him to get paid for helping with the setup. And while we might feel bad for Greg, who’s threatened with being outed against his will, this is still a guy who brags to his friends about sexually assaulting women.

But in terms of irredeemable characters, nobody can hold a candle to Sebastian himself. The movie begins with Sebastian screwing over his hypocritical and uncaring therapist by exposing her “great parenting” schtick as a scam: He seduces her daughter, Marci (a very funny and tragic Tara Reid), and then disseminates Marci’s half-naked photos, photoshopped onto her mother’s book cover, all over the internet; the (troubling) implication is that a good parent wouldn’t have raised a “slut.”

Marci, whom we don’t see enough to get to know, is one of just a couple characters in the movie who don’t seem to deserve such a horrible fate. The other is Sebastian and Kathryn’s favorite pawn, Cecile, whose only crime is naivete. Her “sexual awakening” is spun as a positive — “You’re a woman now,” Kathryn tells her, after Sebastian goes down on her and gives her her first orgasm — but Sebastian and Cecile’s sex scene is pure coercion; Cecile never consents to what happens to her.

Problematically compelling anti-heroes are a dime a dozen these days, but how are we ever supposed to root for Sebastian, the sexual assaulter and purveyor of revenge porn? He’d be far from the first bad boy character who goes good after meeting a virtuous woman who shows him the error of his ways. But unlike, say, Heath Ledger’s character Patrick Verona in 10 Things I Hate About You, which came out that same year, Sebastian’s not a tough working-class kid with a secret heart of gold, who agrees to a bet to make a quick buck — he’s a mega-rich asshole who treats women as conquests, with only the prospect of further conquests spurring him on.

Reese Witherspoon’s Annette, too, isn’t anything like Julia Stiles’ indelible Kat Stratford. Kumble has said that Witherspoon only agreed to join the project if she could work with him on the script to strengthen her role, “so she wasn’t a doormat.” Annette stands up to Sebastian initially, but in typical teen-movie fashion, it just takes a couple dates — with someone she’s been warned is a master manipulator — to believe that he’s truly changed, abandoning her pledge to abstinence and her longtime boyfriend in one fell swoop. It’s hard to imagine how much of a pushover Annette’s character was before Witherspoon insisted on giving her some autonomy.

To be fair, it seems the audience is also supposed to believe that Sebastian has truly changed — he passes on his first opportunity to sleep with a consenting Annette, which would have won him his bet with Kathryn; instead, he tears up and leaves the room, suddenly struck by a new conscience. Still, it’s a suspiciously lightning-fast evolution. And, also in typical teen-movie fashion, it’s the pitch-perfect soundtrack that’s largely responsible for emotionally manipulating us into buying that evolution, as viewers. Kumble told Cosmopolitan that Counting Crows, after seeing an early cut of the movie, recorded “Colorblind” for Sebastian and Annette’s climactic sex scene. It’s such a perfect few minutes of film, you almost don’t really care that it feels completely incongruous with the rest of the movie — in that it’s actually very sweet, and tasteful.

I don’t believe there’s such thing as spoilers for a movie that came out 20 years ago, but be warned that I’m about to describe the film’s ending, in case you’d like to go back and re-experience it for yourself (or, perhaps, experience it for the first time) before reading. There’s a lot of drama in the build-up, but the short version is this: Sebastian jumps into traffic to push Annette out of harm’s way, saving her and killing himself in the process.

The ending of Cruel Intentions' source material was no less mysterious in the late 1700s.

Kumble wrote the scene following Sebastian’s death with the Verve’s “Bitter Sweet Symphony” in mind, and convinced the studio to pay handsomely for the song. The splurge paid off; if you remember any scene most clearly from the movie, it’s probably this one. It turns out that Cecile and Annette have made copies of Sebastian’s journal, detailing his and Kathryn’s many unsavory exploits, leading the headmaster to discover that the Kathryn’s iconic cross necklace is filled with cocaine. She sheds a single tear, her reputation now ruined, while Annette escapes in Sebastian’s Jaguar, wearing his tiny sunglasses, his notebook riding shotgun with her. Did Sebastian leave the car to her in his will sometime over the last two days? Probably not, but who cares! It’s a fabulous ending, if a completely confounding one.

In David Coward’s introduction to the 1995 Oxford World’s Classics translation of Les Liaisons dangereuses, he wrote that the ending of Cruel Intentions’ source material was no less mysterious in the late 1700s. Then, as now, readers couldn’t agree on whether Valmont truly loves Madame de Tourvel (the analog to Annette), or whether he loves no one at all — whether his death is an honorable form of suicide, or else, Coward wrote, “the logical outcome of the dangerous game they play: their mutual annihilation is as predictable as the harm done to casual bystanders.”

Cruel Intentions also offers us those two competing readings: noble and tragic sacrifice, or deserved comeuppance for selfish sociopathy? Sure, Sebastian is able to screw Kathryn over even in death, which is impressive. But did he really “win”? The guy’s still dead.

After Cruel Intentions’ extraordinary success, Kumble landed a follow-up TV series, Manchester Prep, but it never got off the ground. The hourlong drama, which culled characters from the movie, following them at their elite Manhattan prep school — a proto–Gossip Girl — got the ax before it even aired; Fox cited “creative differences” with the studio, Columbia TriStar.

“Just as Cruel Intentions was criticized for being a teen-friendly R-rated movie,” wrote Joal Ryan for E! News in 1999, “Manchester Prep was raising eyebrows for being a so-called ‘family hour’ show (positioned in the 8-9 p.m. time slot) with eyebrow-raising plot devices.” (The first episode featured a teen girl ogling her stepbrother’s penis in the shower.)

Before getting the chop, Kumble made some concessions in adapting the depravity of Cruel Intentions for TV. According to the LA Times in 1999, “even in this television season, where networks are scrambling to compete with edgier cable competition and nothing seems too far-fetched, some changes had to be made: The cocaine is gone, as is the profanity that laced the movie. A scene from the R-rated film that involved two girls kissing now takes place between a boy and a girl.” But then the Parents Television Council got word of an Entertainment Tonight exposé, in which cameras “caught the series filming a scene where one girl shows another how to get sexual pleasure from horseback riding.” It was all downhill from there.

Kumble cut the dumped series into a direct-to-video movie, launching the screen career of one Amy Adams, but neither Cruel Intentions 2 nor several of the other Cruel Intentions spinoffs after it were able to capture the same mania of the original. A few years later, when Gossip Girl landed on the CW, it became clear that there was, in fact, a significant and enthusiastic television audience for stories about mean rich kids screwing each other and screwing each other over. But neither that series nor much else that’s followed it have achieved anything like the shameless perversity of Cruel Intentions.

Perhaps what was so upsetting to those parents was not merely the idea of (fictional) teenagers indulging in sex and drugs and petty machinations onscreen, but rather the moral ambiguity, or even nihilism, of Cruel Intentions — which it inherited from its source material. Coward wrote in his introduction to Les Liaisons dangereuses that even now, it’s impossible to know Laclos’s intentions in writing the book. “Is freedom achieved by abandoning the moral ideals and social constraints which stand in the way of personal gratification? Or does true self-fulfillment lie in subordinating the self, respecting the feelings of others, and accepting the rules of civilized conduct?” Most of Laclos’s contemporaries, Coward said, “read the book as though it were a user’s manual for aspiring seducers.” Yet he “never provided a satisfactory explanation of what he had set out to do or what he had achieved.”

Since it’s more or less impossible to glean takeaways about virtues and values from the text, Coward wrote, “Perhaps we should see Les Liaisons dangereuses less as a metaphysical tale of evil than as a practical fable about winning and losing.” I like the idea that we can read Cruel Intentions that way, too: not a hero’s tale of Goodness triumphing; or even of love conquering all. Instead, it’s a story about the fact that no matter what you do, no matter how “good” you are, or think yourself to be, sometimes you’re on top and sometimes you’re not. It’s about sex, power, and chaos. Twenty years later, I’m still here for it. ●

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