Why Were We So Into Cruel Intentions?

Earlier this week I was listening to one of my favorite podcasts, The Bechdel Cast, as they talked about one of the movies that defined my late teens: Cruel Intentions.

Now, I saw this movie looong after it came out, as I was a six-year-old when it debuted in 1999, but many years later when I was sixteen, I finally watched it, and in a rare feat, I’d actually read the French book, Les Liaisons Dangereuses, first. Cruel Intentions is one of the movies that when you rewatch it, there is a whole lot of yikes, and as I was listening to the podcast episode, I was thinking, “How did we get sucked into this movie?” and then I rewatched the trailer.

That is a trailer. When “How Soon is Now” started playing, I think my eyes started to water a little bit with nostalgia about how that song defined an entire era of angsty well-dressed teenagers in movies to do the most. And witches.

It also reminded me that the reason I was really into this movie had to do with one character and one character alone: Kathryn Merteuil, as played by Sarah Michelle Gellar, (and Amy Adams in the prequel). Kathryn is a mean girl who uses her money, sexuality, and status in elite New York City society circa the late-’90s to have control in ways that, onscreen, seem worthy of envy, even though we know it’s just a second Gilded Age.

For those unfamiliar with the movie who don’t feel like loading a trailer, Kathryn and her narcissistic step-brother, Sebastian Valmont (Ryan Phillippe), have a bet. Kathryn wants Sebastian to seduce a young girl named Cecile (Selma Blair) in order to take revenge on Court Reynolds, her ex-boyfriend, who left her for Cecile. Sebastian is slightly booked because he wants to seduce Annette Hargrove (Reese Witherspoon), who wrote an entire article about why she is waiting for love to lose her virginity.

In response to this, Kathryn and Sebastian make the following wager: if Annette doesn’t sleep with Sebastian, Kathryn gets his vintage Jaguar XK140 (having just watched Mad Men, I feel I understand this more). If Sebastian wins, Kathryn will have sex with him—and by sex, what they really mean is anal sex, because it’s the ’90s.

The plot is very sexist and includes a lot of manipulation that makes most of the sex scenes rape by standards that we understand today. Those aspects of the movie render it very much unwatchable, and The Bechdel Cast explains it very well, but I also remember that I myself didn’t watch the movie for Sebastian/Annette and that dynamic. I watched it because of Kathryn.

Kathryn is a character that, if written a little bit better, would easily find her place in a Megan Abbott or Gillian Flynn novel or even a high school version of A Song of Ice and Fire. She is a female character who has internalized sexism because of the sexism she has experienced in her life, and that rings true in one scene where she delivers his rant to Sebastian:

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. So there’s your psychoanalysis, Dr. Freud. Now tell me, are you in … or are you out?

It’s a more hackneyed version of Amy Dune’s “Cool Girl” rant in Gone Girl, and while both have been rightfully critiqued, there’s still a reason why scenes like this, even when in shallow movies like Cruel Intentions, can so resonate: that tiny sparkle of truth within them.

When it comes to women and their sexuality, there is still a huge obsession with “the number,” and even the most sexually empowered can sometimes either be shamed or feel some moment of doubt when it comes to their sexuality. This isn’t to say that virgins don’t get shamed as well; they absolutely do, but “purity” has always been more valued in our patriarchal society than having multiple partners, not to mention the pressure to be nice, polite, and “Mary Sunshine” in order to not be seen as a “bitch.”

The fact that Kathryn games the system, seeks out revenge, and is a really dark character is what makes her so compelling. That she is a really wicked villain without any tragic backstory beyond I’m petty and terrible. She may not be a feminist icon, but Kathryn Merteuil embodied the desire to be bad and look good doing it. She gets kicked off her throne in the end, but she doesn’t die, which is pretty refreshing.

Also, let’s not forget that the tragic reformed hero of Cruel Intentions, Sebastian, starts off the movie revenge porning his Doctor’s daughter, and decides that he wants to seduce Annette because she’s a challenge. All of that happens before Kathryn even comes into the picture, and yet she’s the one who must end the movie being shamed for her actions, while Sebastian has changed over the course of what … six days, because he falls in love with Reese Witherspoon?

I love Reese Witherspoon, and even I think that’s unrealistic. Plus, it reinforces the underlined message that Annette and her purity and innocence is more powerful that Kathryn and her experienced and self-empowered sexuality.

Cruel Intentions is one of those movies that is hard to rewatch, but also deeply compelling at the same time. Plus, if anything, it gave us Sarah Michelle Gellar with dark hair and some amazing ’90s time capsule outfits in the theme of dressing teenagers like hot moms.

What are some movies that looking back you can’t believe that you loved?

(image: Columbia Pictures)

Want more stories like this? Become a subscriber and support the site!

—The Mary Sue has a strict comment policy that forbids, but is not limited to, personal insults toward anyone, hate speech, and trolling.—