Why ‘Cruel Intentions’ Is Deeply Problematic 20 Years Later

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.

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.

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.

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.