Why ‘Cruel Intentions’ Is Deeply Problematic 20 Years Later

It was a rainy Friday evening when my husband and I curled up to watch the 1999 teenage sex romp Cruel Intentions. Vintage Sarah Michelle Gellar. Reese and Ryan back when they were still an item. Selma Blair before she was the go-to witchy brunette. And the whole thing was based on an 18th-century French novel. What’s not to love?

A lot…as it turns out. See, whereas high school ’90s classics like Clueless and Romy and Michele have actually aged better with time—and proved themselves paragons of feminist-leaning rom-coms—this one is wildly problematic. Like, how was it ever socially acceptable?

In case you haven’t seen the film lately—which you should for the sheer horror’s sake—allow me to refresh your memory, in the wake of the 20th anniversary.

sarah michelle gellar ryan phillippe cruel intentions
Columbia Pictures/Getty Images

First Of All, There’s The Incest

Set in the land of Manhattan’s elite, Kathryn Merteuil is presented as a sort of Blair Waldorf meets Machiavelli. The central problem we’re supposed to buy is that her classmate Cecile (Blair) has accidentally stolen her ex-boyfriend, Court Reynolds. Kathryn then hatches a plan to convince her stepbrother, Sebastian (Phillippe), to seduce Cecile and ruin her name.

But he’s already busy trying to deflower Annette (Witherspoon), the “paradigm of chastity and virtue” who is saving herself for marriage. So, a wager is made: If Sebastian is unable to seal the deal with Annette, Kathryn gets the keys to his beloved vintage Jaguar. If he’s victorious, then he gets to sleep with Kathryn—His. Step. Sister. Now, she’s not his sister by blood, but for the sake of this argument (and most others), I’m going to categorize this as incest. And prostitution. It’s gross, guys, and that gorg antique four-post bed doesn’t make it any less gross.

sarah michelle gellar sean patrick thomas cruel intentions

And Casual Racism

With the bet made, the moral wreckage begins. In an effort to get information about Annette, Sebastian convinces his friend Blaine Tuttle (Joshua Jackson) to mess around with her closeted gay ex-boyfriend and film it, then blackmails him. Then, Kathryn ups the ante by throwing around some blatantly racist comments about Cecile’s music teacher, Ronald Clifford (Sean Patrick Thomas).

When Kathryn learns that Cecile and Ronald are into each other, she tells Cecile, “Listen to me. Your mother must never know. Never,” because of his race. Then, she turns around and informs Cecile’s mom about the mutual crush and warns it “could destroy her reputation at Oakwood.”

Aside from being offensive, this is just lazy scriptwriting. The writers could have used any other reason for Kathryn to break up Cecile and Ronald aside from race. Anything.

cecile and katherine cruel intentions1

The Film Lionizes ‘no-means-yes’ & Victim-blaming

Sebastian lures young, naïve Cecile to his mansion under the pretense of giving her a letter from Ronald. He then forces himself on Cecile and performs oral sex on her. Oh, and when Cecile tells Kathryn she feels uncomfortable with what transpired, Katherine shames her into silence and suggests she get as much experience as possible so she can please Ronald in bed. A woman telling another woman to ignore her own sexual boundaries for the sake of a man? Holy reduced agency, Batman!

But Sebastian’s sexual manipulation doesn’t stop there. Instead, he proceeds to mold himself into the kind of man Annette might be interested in, convince her to love him and then takes her virginity. Then because of the absurd moral compass at play here, we’re supposed to think it’s OK because he realizes, after he breaks her heart, that he actually loves her.

sarah michelle gellar cruel intentions
Columbia Pictures/Getty Images

And Oh So Much Sex-shaming

In the end, Sebastian is held up as a scapegoat and literally dies for/because of his love. Annette reads his journal, which outs Kathryn as a potential sociopath, and shares it with the crowd of people at Sebastian’s memorial.

Sebastian’s entries point out Kathryn’s bulimia, “coke problem” and dalliances with many men. For the purposes of plot, this is cathartic and calls to minds Kathryn’s several arguments against sex shaming throughout the film. And yet, as everyone turns to look at Kathryn with disgust, all I could think was, Really? Kathryn’s hyper-sexuality and precarious mental health is what makes her a social outcast? How about her mistreatment and manipulation of literally everyone around her? How about her racism? How about about pushing other women into sexually compromised positions?

I don’t consider myself a Pollyanna moralist, and I recognize that we have to view films in the context of the world in which they were made. But I refuse to believe that 1999 was such a backward time that we blindly laughed along to victim-blaming and sexual assault.

After all, this is the era that brought us Cher Horowitz, Buffy Summers and Elle Woods—proof that we could do better.

Lex Goodman

Cat mom, yogi, brunch enthusiast

Lex is an LA native who's deeply obsessed with picnics, Slim Aarons, rosé, Hollywood history and Joan Didion. She joined PureWow in early 2017.
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