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In a recent New York Times interview about her long-awaited return to acting, Sarah Michelle Gellar made an interesting connection between two of her films. In 1999, at the height of her Buffy fame, Gellar played Kathryn Merteuil, a conniving teenager who attends an elite Manhattan high school. Now, in 2022, Gellar has returned to the big screen (or the small screen, as it were) in Jennifer Kaytin Robinson’s Netflix film Do Revenge, playing the headmaster at a similarly distinguished school in Palm Beach, Florida. 

In the interview, Gellar confirms the fact that she and Robinson thought of Gellar’s headmaster character as the grown-up version of Kathryn from Cruel Intentions. This connection makes a lot of sense. Along with the numerous ‘90s needle drops, Gellar’s presence in the film is another way Do Revenge attempts to pay homage to the ‘80s and ‘90s teen films it clearly draws from. Moreover, it’s not hard to imagine Kathryn continuing her high school reign by being in charge of a school much like the one she once attended. 

This apt comparison brings up some interesting questions. ‘80s and ‘90s nostalgia is all the rage these days, and Do Revenge is clearly a part of this trend. But a lot has changed since the ‘90s, and these homages will necessarily have many departures. Cruel Intentions is a very dark film, and Do Revenge, well, it tries to be – as much as it can beneath the glossy, hyper-stylized veneer that’s now become synonymous with the Netflix brand. Interestingly enough, both films interpolate queerness into the story, but with very different intentions. There are also some stark differences in the moral lessons the films purport to teach us. 

If you haven’t seen it in a while, you might have forgotten. Cruel Intentions is a thorny, sinister film, and it has a pitch-black heart. Step-siblings Kathryn and Sebastian (Ryan Phillippe) dress and act like adults, all while proving that teens can be just as evil, horny, and devious as their grown-up counterparts. The central premise of the film is this: Kathryn makes a bet with Sebastian that he can’t deflower the new girl, Annette (Reese Witherspoon) – a professed virgin until marriage – by the end of the summer. If she wins, she gets his vintage car, and if he wins, she will “fuck his brains out,” something he’s always wanted. What’s a friendly bet amongst step-siblings? 

Meanwhile, Kathryn is hell-bent on getting revenge on her ex, Court (Charlie O'Connell), who unceremoniously dumped her at the beginning of the summer. Kathryn enlists Sebastian’s help in seducing (and thus spoiling) the naive Cecile (Selma Blair), who Court now has his eyes on. Sebastian is a notorious womanizer and playboy, and he seems to mainly be in it for the fun. On the other hand, Kathryn’s stake in the mission feels righteous. Though she’s not opposed to having fun along the way, her whole plan revolves around taking down Court, and she doesn’t care who she takes down along with him. 

Kathryn is shrewd and cunning, and she is clear-eyed when it comes to the double standard regarding men’s and women’s behavior, especially in terms of sex. The most cheer-worthy moment in the film comes about halfway through, when Kathryn gives her famous monologue. On the off chance that you don’t have it memorized by heart, it bears repeating here.

Eat me, Sebastian! It's okay 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 want to kill myself. 

It’s hard not to nod along to Kathryn’s tirade, but in the end, she can’t win. There are a number of (arguably) more subversive erotic thrillers from the 1980s – Body Heat and The Last Seduction are two great examples¹ – where the femme fatale gets away with her dastardly deeds. But Cruel Intentions is not that movie. Here, the femme fatale doesn’t win, though she makes some good points along the way. 

It ends like this: Sebastian winds up falling in love with Annette, but Kathryn convinces him to break it off with her to protect both of their reputations. Sebastian then saves Annette from being hit by a car, redeeming himself and becoming a martyr in the process. While Kathryn speaks at his memorial, Annette and Cecile distribute copies of Sebastian’s journal, a document that reveals all of Kathryn’s devious schemes. Kathryn is caught (and presumably punished), while the good girls come out on top. 

While there must have been plenty of viewers who were rooting for Kathryn during the film’s original run, her character is even more well-suited to becoming a beloved (anti)heroine today. Think, for example, of the semi-ironic “girlboss” language that is used to describe ostensibly villainous female characters, or the “I support women’s rights, but I also support women’s wrongs” memes. Ask any woman cinephile who her favorite heroines are, and there’s a good chance you’ll get Gone Girl’s Amy Dunne as a response.

 Whether or not the film is cynical or optimistic depends on your perspective. In one sense, Cruel Intentions is an optimistic movie – the good girls come out on top, and good triumphs over evil. In another sense, it’s deeply cynical. Kathryn can’t get what she wants because, as she correctly diagnoses in her famous monologue, the world is a sexist, unfair place. On the other hand, Sebastian, in his martyrdom, gets exactly what he wants. 

But is Kathryn really the villain? The only person we really see Kathryn hurt is Sebastian (and theoretically Cecile, but she doesn’t really seem hurt by any of Kathryn’s machinations). We know, on the other hand, that Sebastian has left behind a string of brokenhearted women – his therapist's daughter, for one, whose naked pictures he spread all over the internet. 

Whether Kathryn is really the villain or not doesn’t matter. Within the world that the film presents, it’s not possible for Kathryn, Cecile, and Annette to all get what they want. It’s a zero-sum game. This means there is a clear dichotomy: Kathryn’s revenge against Sebastian (and Cecile and Annette) is seen as illegitimate, while Cecile and Annette’s revenge is seen as righteous. From this angle, Cruel Intentions is a deeply cynical film. If you’re rooting for Kathryn, the ending might not be satisfying for you. But it’s also realistic – of course Sebastian would get away with everything, while Kathryn would be punished – even if it leaves us with a sour taste in our mouths. Indeed, cynical movies are often more interesting than wholly optimistic ones. The knottiness we feel is stimulating, and thought-provoking. 

Do Revenge is a whole different beast. It tries to be knotty (and naughty), but ends up sugary instead. The film is populated with seemingly archetypal characters. There’s Drea (Camila Mendes), a popular girl who doesn’t have the same wealth as her peers but is desperate to keep up appearances. Were this Mean Girls, she would most certainly be one of the Plastics, though she likes to think she’s a better person than her peers.

Then there’s Sarah Michelle Gellar’s headmaster character, who, after Drea punches her ex Max (Austin Abrams) for releasing naked pictures of her (sound familiar?), tells Drea to “channel that anger into getting what you want.” The headmaster is clearly meant to be a Gen X “girlboss” character – her connection to Kathryn becomes clear here – and the students view her as such. (In the most accurate sentence uttered in the entire film, Eleanor says: “I want her to hit me with her Tesla and then reverse back over me.”)

Next, we meet Eleanor, who first appears as a grungy, almost pathetic lesbian character. Eleanor tells Drea that a girl she once had a crush on outed her and told everyone she was a predator, and, like Max, she never got in trouble for it. And therein lies the problem that Drea and Eleanor are faced with: people constantly get away with shitty things and never face any consequences. As in Strangers on a Train, Drea and Eleanor decide to swap problems and “do” each other’s revenge: Eleanor will go about taking down Max, while Drea sets her sights on Carissa (Ava Capri). 

The film constantly references teen movie tropes. There’s a makeover sequence that Eleanor winkingly calls “so problematic,” and Drea even gets her own Cruel Intentions-esque monologue where she describes to Eleanor the double standard regarding men and women’s behavior. Later, Drea releases Max’s texts during a speech he’s giving about female empowerment – just like the end of Cruel Intentions when Sebastian’s journal is distributed while Kathryn is speaking at this memorial. When the previously uncool Eleanor starts getting a little too chummy with the rich kids she’s meant to be taking down, it’s hard not to think of Mean Girls. 

Do Revenge is filled with lots of twists and turns, including an ostensibly shocking third-act twist that I won’t spoil here. But, in the end, it’s hard to really root for the characters. Their deviousness just doesn’t hit in quite the same way that Kathryn’s does, nor are they righteous or maligned enough to really sympathize with. That’s not to say that what every movie needs are oversimplified personifications of good and evil. But while the movie attempts to play in the gray area – Is their revenge justified? Are Drea and Eleanor really the good guys? – it winds up just leaving everything more muddled. Drea and Eleanor are constantly hurting each other, but we’re also supposed to believe they care for one another. In the end, it’s less a sense of moral ambiguity than it is a lack of cohesion.

In the film’s conclusion, everyone is forgiven, and all the knotty, hard-to-digest parts are smoothed over. Though our previous belief about who the good guys and the bad guys are is thrown into flux in the final act, everything is put back into place by the time the credits roll. It’s certainly more optimistic and happy-go-lucky than the end of Cruel Intentions, but this also makes it far less interesting. 

Sarah Michelle Gellar – who is a goddess that you will never hear me criticize in any way – thinks the ending of Do Revenge is more reflective of the opinions of the “youth of today.” Gellar contends that Kathryn couldn’t have a happy ending because she wouldn’t let herself have one, while young people today “feel like they deserve the happy ending.” It’s a fair point, and it certainly has some merit. But the world does tend to feel like it’s ending on a daily basis, and doesn’t that mean people are more cynical than ever? A cursory look at the gallows humor that populates social media would seem to support this argument. 

That’s not to say that Do Revenge should have been more like Cruel Intentions, or that there hasn’t been meaningful social progress since the first film was released. Consider, for example, how the two films depict queerness. One of the most famous scenes in Cruel Intentions is the kiss between Kathryn and Cecile. It’s clearly meant to be titillating (just look at how it’s shot), but it also serves a clear narrative purpose. It illustrates Kathryn’s impressive sexual prowess and Cecile’s respective inexperience. The word “fag” is uttered several times throughout, but Sebastians’ best friend is also gay, and both he and Kathryn seem to see themselves as being too “evolved” for that kind of bigotry. In this sense, both queerness and homophobia are normalized in the film, though neither is central to the story. 

On the other hand, in Do Revenge, the queer character does have a say in how she’s treated. In fact, that is the driving force of the film. But, at the same time, the homophobic bullying Eleanor experienced in middle school isn’t given the weight it deserves, and she rather unceremoniously forgives her tormenter in the end. In a way, both films normalize queerness and homophobia simultaneously, though the moral lessons proposed therein are quite different. 

When it comes to contemporary teen films that try to emulate the films of the ‘80s and ‘90s, there always seems to be something missing. Even Crush, which I generally liked, never quite succeeded in the way its predecessors did. Perhaps part of this is the obvious fact that when one film emulates another, these comparisons are hard to avoid. And indeed, maybe it's impossible to recapture the magic of the past, especially considering our rose-tinted perception of it.²

But there’s also something to be said for films that aren’t easily digestible or morally righteous. It’s often more interesting to interrogate the cracks than to smooth them over. At a certain point, it becomes tiring when so much of contemporary film and television is so self-referential and self-aware. In many ways, this preempts any criticism or meaningful discussion one might have about the film’s moral rectitude and the gray area therein. The characters in Do Revenge (and indeed, the youth of today) have more language to talk about their problems than the teens of Cruel Intentions did, and it makes sense that the film mines contemporary pop culture vocabulary in this way. But does that make for a better movie? 

Kathryn Merteuil may have been rotten to her core, but isn’t that precisely what we love about her? If Do Revenge is her redemption, then maybe it’s best she stays in the past, where she belongs.