Mention Cruel Intentions to anybody aged 25 to 35 and you’ll likely elicit a passionate reply — and one will be mine.
When it came out in 1999, I was 12. And when I secretly acquired the VHS tape a year later, it became a private obsession. But despite wearing out my childhood copy, it was only when I revisited the film this year, ahead of its 20th anniversary, that I understood why I connected so strongly with material that was lifted from 18th Century literature and sounds ridiculous on paper: a certain queerness pervades the story.
At the time of its release, Cruel Intentions was best known for the same-sex kiss between Sarah Michelle Gellar and Selma Blair, a gratuitous and frequently parodied moment which pandered to a straight male audience and bolstered the film’s reputation as more “provocative” than other teen movies. That infamous strand of saliva might have launched a thousand sexual awakenings, but the underpinning I’m referring too is far subtler, and requires a more critical reading.
Take Kathryn Mertueil (Gellar), the film’s antagonist. In her very first scene, she’s depicted as the perfect daughter. It is only once everybody leaves and she is alone with her brother Sebastian (Ryan Phillippe) that she shows her true self. Perpetually portraying Pollyanna to the outside world while concealing her inner life, the character is in a closet of sorts, subtext which becomes text when she delivers a monologue about gender roles and double standards halfway through the movie:
“Eat me, Sebastian. It’s all right for guys like you and Court to fuck everyone, but when I do it, I get dumped for innocent little twats like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish the fact 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 the closest the movie ever gets to really reckoning with the virgin/whore dichotomy it perpetuates between Kathryn and the other female characters, illustrating how Kathryn does whatever she can to exercise agency within the polite, patriarchal society that constrains her. When I rewatched the monologue as an adult, it struck a chord, because what closeted teenager hasn’t felt the need to play a role at some point, to suppress themselves and try to be the person their families expect them to be?
This time around, I noticed Kathryn’s vulnerability, which she is loathe to reveal. Cruelty is a mask Kathryn wears to protect herself, like so many young gay men who learn to be cutting as a means of self-preservation. The only moment when she is unable to hide is in the film’s famous final scene, which sees her “outed” to her community. We are supposed to see this as a comeuppance – and it is – but read through a queer lens, laying all of Kathryn’s secrets bare is a ritual humiliation, the kind which destroys real lives, and watching today, I couldn’t help but feel a pang of sympathy for her.
In stark contrast to Kathryn’s louche sophistication, Cecile (Selma Blair) is comically naïve when it comes to sex — and I see myself in her character, too. Her naivety makes a degree of sense, considering her counterpart in the source novel was an ingénue who spent her entire childhood in a convent. It also speaks to the general cluelessness I felt in my early teens; I knew that I was attracted to boys, but I didn’t know exactly what that meant. Later, when I came out, I was bombarded by all kinds of intrusive questions about my sexuality that I had no idea how to answer, and which took me the rest of my teens to figure out. Growing up in the suburbs with limited Internet access was like my convent.
When I recently tweeted that I was rewatching Cruel Intentions, I was bombarded with gifs from the movie from gay men almost exclusively. And while there are a whole bunch of superficial reasons you could cite as why the movie speaks so keenly to that demographic — it helped to launch the universally beloved Reese Witherspoon as a movie star; it features high-camp performances by Christine Baranski and Swoosie Kurtz; Joshua Jackson has a fun, progressive-for-1999 cameo as a gay student; the soundtrack continues to slap, two whole decades later; and there is a highly important scene in which you see Ryan Phillippe’s butt — I actually think it’s the ever-present hint of transgression that queer viewers really identify with. Sebastian and Kathryn aren’t doing things teenagers are supposed to do; they’re leading their peers astray, and the viewer along with them. What could be more appealing?
A television reboot of Cruel Intentions, which would have focused on a new generation of characters, was recently nixed, and that’s probably for the best. As much as I’d love to see this story play out in the age of social media, I doubt you could capture lightning in a bottle twice. The film’s ability to weave baroque storytelling into a crowd-pleasing high school movie, combined with a deliciously wicked leading performance by Gellar, meant it was destined to be a queer cult classic — and ultimately, one of a kind.
Feature photo via Everett Collection.