Revisiting Cruel Intentions 20 Years Later

The opening scene of 1999’s Cruel Intentions certainly sets the film off with a bang. Opening in a therapist’s office in New York City, we are quickly introduced to our charming anti-hero Sebastian Valmont, a sophisticated young Lothario from the Upper West Side, as he speaks about his sex addiction. When he leaves the room, the snobbish therapist receives a panicked call from her daughter – she let a young man take nude photos of her and he has subsequently published the photos online. As the website repeatedly chimes “you are a slut” to the now screeching therapist, the culprit is revealed to be none other than Sebastian himself; certainly an interesting way to introduce the character we’re supposed to be rooting for.

Cruel Intentions was released in the tail-end of a decade defined by teen films such as Dazed and Confused, Clueless and The Craft. Starring the Ryan Phillippe, Sarah Michelle Gellar and Reese Witherspoon, the film was a loose adaptation of the French novel Les Liaisons dangereuses and followed teenage step-siblings Sebastian Valmont and Kathryn Merteuil as they attempt to ruin the life of the innocent Cecille Caldwell; the cause of Kathryn’s recent break-up with her ex-boyfriend Court. Their plan? To sexually corrupt Cecille, therefore destroying her reputation and forcing Court to lose interest. Along the way, Sebastian attempts another conquest, the seduction of the new headmaster’s virginal daughter, Annette Hargrove. Rather than portraying a simplistic example of puberty, popularity and high school, Cruel Intentions delved into ideas of class, reputation and sex as a source of power. The twisted teens were more akin to adults, sporting a level of sophistication that Cher Horowitz could only dream of. Their schemes and lies ruining life after life until boiling point is finally reached. While the reviews remained mixed, the tantalising plot both shocked and delighted cinema-goers around the world. Labelled “the dirtiest-minded American movie in recent memory”, the film was quickly cemented as a cult classic.

Naturally, like most things pre-2016, significant aspects of Cruel Intentions’ plot could not possibly be made nowadays. While certainly an anti-hero to the highest degree, Sebastian’s “revenge” against his therapist would not sit in this post-#MeToo world, regardless of the grey morality of the character being portrayed. When the impressionable (and distinctly young) Cecille Caldwell is pressured into letting Sebastian perform oral sex on her, what may have been intended to be humorous scene instead appears sinister and uncomfortable. Upon re-watch in 2019, these events coupled with Sebastian’s animosity towards Annette and blackmailing of closeted student Greg would almost make you forget that he is meant to be our hero. Dashingly devious, it is oftentimes difficult to tell the difference between sincerity and manipulation during his scenes. While his eventual falling for Annette is certainly gratifying in a sense, it almost arrives too late within the film’s plot for the audience to forget that he is actually not a nice guy, particularly in this day and age.

In turn, Cruel Intentions introduced one of the most complex female characters to ever grace the teen-genre. The glamorous and cold Kathryn housed a chip on her shoulder and a coke addiction that inspired the hundreds of hollow cross necklaces currently being sold on Etsy. Regardless of the intention, the now-iconic quote “I’m the Marcia-fucking-Brady of the Upper East Side, and sometimes I want to kill myself” spoke to a generation of girls forced to conform to lady-like behaviour and stifle their own sexuality in order to appear more likeable to others. While she is still a ginormous bitch, hellbent on destroying the lives of many innocent (and not-so-innocent) people, Kathryn’s rage appears to at least be caused by societal pressure and the stifled life she is forced to lead, rather than Sebastian, who provides the audience with little justification for his wrong-doings. As a character, Kathryn had the potential to speak volumes for how young women are thought to police their sexual desires, but instead she is vilified, exposed as both a coke-addict and a sexual being, with the virginal Annette coming out on top.

While I certainly enjoy the plot of Cruel Intentions despite its problematic aspects, revelling in the intricate tale of schemes coupled by an excellent late-nineties soundtrack, I cannot help but feel that Kathryn’s life as both a villain and a victim would have been a more interesting tale. The ideas that the film touches on, such as the concept of sex as a tool and weapon, would have been perhaps more interesting to examine in the context of a woman playing the game to her advantage, rather than a man who made up the rules. Instead, what we do get is a critique of the scheming and manipulative ways of the Upper Class, which certainly made good strides but stops just short of truly pushing the envelope. At least we still get to witness Sarah Michelle Gellar snort coke from a cross necklace, passionately kiss Selma Blair in Central Park and wreak havoc for everyone she has ever met. That is the true reason this film is still remembered 20 years later and we all know it.


by Amy Louise

Amy Louise O’Callaghan is a filmmaker and illustrator from the tiny city of Cork, Ireland. When she’s not watching films, she enjoys drawing and playing lots of video games, but never actually finishing them. Some of her favourite films include Heathers, Carrie, Suspiria (1977) and The Little Mermaid. She’ll watch almost anything, but particularly enjoys cheesy horror films and anything from the teen genre. You can follow her on Twitter here and on Letterboxd 

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