I Just Watched The OG Cruel Intentions For The First Time & Whoa, The Sexism

I was 16 when Cruel Intentions opened in theaters in 1999. In many ways, I was the perfect audience member for the teen flick: I was in high school, lusting after senior boys, and listening to The Verve's "Bittersweet Symphony" made me feel things. But, in reality, I wanted nothing to do with that movie. I was a big film nerd at heart, so my movie preferences aligned more with The Insider, American Beauty, or Girl, Interrupted. On top of that, I wasn't a big Ryan Phillippe fan (sorry, Ry), and watching bad rich kids do bad things to each other didn't interest me. Been there, done that.

As we all know by now, though, the '90s are cool again. I mean, I don't think they were ever not cool, but the nostalgia pull is oh-so-real these days — to the point that a Cruel Intentions TV series just dropped on Prime Video on Nov. 21.

So, as a dating and sex writer, I thought it was my duty to watch one of the most sexually explicit teen movies of its era. And 25 years later, here are my thoughts about finally watching the movie (and that scene between Sarah Michelle Gellar and Selma Blair that made every girl my age giggle and gush).

Cruel Intentions revisited

For those who need a refresher, Cruel Intentions is loosely based on the novel Dangerous Liaisons by Pierre Choderlos de Laclos. Sebastian (Phillippe) and Kathryn (Sarah Michelle Gellar), a pair of diabolical step-siblings, hold a wager of sexual conquest involving Annette (Reese Witherspoon) when she writes an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend.

Sebastian bets he will woo Annette into bed while Kathryn bets against it, and if she wins, Sebastian will have to sleep with her. However, Sebastian gets more than he bargained for as he finds himself falling for Annette.

Twisted, right?

First impression: Horrible people

These people suck. Am I the only one who doesn't root for the bad guy? If you're a horrible person, I want you to lose. I don't care how good-looking you are. Right off the bat, we know Sebastian is awful — he leaked poor Tara Reid's nudes. He also just reeks a$$hole.

Kathryn is not any better (although SMG as a brunette is *chef's kiss*), as she's attempting to corrupt Blair's character, Cecile. Also, because Blair looks like she's perpetually 25 years old, seeing her wear a tight koala t-shirt and acting like she's 13 years old (which I'm guessing is the age that she was supposed to play) was very unsettling.

Regardless, the bet is really messed up. Why do they want to do any of these things beyond the fact that they are selfish, manipulative jerks who have way too much time on their hands? Ah, the beauty of being a teenager, I guess.

The Reese and Ryan chemistry

Reese and Ryan were the It Couple of the '90s, and I think their real romance offscreen was partly responsible for the movie's intense hype. Despite their insufferable characters — even Reese's Annette was annoyingly "too perfect" — those two crazy kids shared some insane chemistry. So much so that, apparently, while they were filming their breakup scene, Phillippe threw up while shooting the scene. Aww.

All about sex

This movie is just about having sex, and maybe I could roll with that if the characters weren't so one-dimensional and mean-spirited. Or if the sex in question was portrayed through a more inclusive, sexual-positive lens. Instead, it all seems… exploitive.

It's the raunchy dialogue (did a blonde Joshua Jackson really say, "The man's got a mouth like a hoover"?) and Sebastian getting Cecile drunk and guilting her into sexual activity. It's peddling out the infamous kiss between Blair and Gellar for titillation's sake. The tongue! The saliva! It's how, ultimately, the entire main plot of the movie revolves around Sebastian scheming to devirginize Annette. It all seems rather ugh.

The sexism element

Speaking of sex (because this is what this entire movie is about), there's a huge sexism element that needs to be recognized. Kathryn and Sebastian both like to have sex. It's actually refreshing to see a female character like Kathryn be so explicit with expressing sexual desire and being confident with her sexual agency.

So, it's disappointing to see her character continually be villainized while Sebastian, the sexual predator that he is, receives a character-redeeming arc and dies a hero. Because Sebastian doesn't just have sex with Annette, he makes love to her. He falls in love with her (or so we're made to believe because, honestly, I don't think those two had nearly enough screen time to convince me that they did and instead relied heavily on the Reese and Ryan chemistry). That's why it's OK for them to have had sex. Meanwhile, we're supposed to love it when Kathryn finally gets her comeuppance. Because she's a slut!

Anyway.

This movie really reinforces the virgin–whore complex in which women are "good" when they're "pure" and "bad" when they're sexually liberated, and that sort of narrative can stay in the '90s.