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By Ashley Teresa
26th February 2019

Before 'Gossip Girl' and the mean queens of the Upper East Side, there was Kathryn Merteuli and Sebastian Valmont. Bored, rich and without apparently any adult supervision, they lied, they snorted, they screwed and they destroyed the lives of anyone who got in their way. Based on the 1782 novel ‘Les Liaisons dangereuses’, ‘Cruel Intentions’ swaps France for New York in a 20th century retelling of the sexual mind games and betrayal. This year marks the 20th anniversary of its release, a sexed-up dark horse that hit the squeaky clean 90s teen film subgenre like a sledgehammer, but still features the same elements.

It’s incredible that ‘Cruel Intentions’ managed to develop such a cult following, particularly since its main plot revolves around incest as a bet prize. Serial virginity-taker and all around womaniser Sebastian (played by Ryan Phillippe, ‘I Know What You Did Last Summer’) sets his sights on Annette Hargrove (Reese Witherspoon, ‘Legally Blonde’, who would become Philippe’s wife that same year), the daughter of their school’s new headmaster who has pledged to save herself until marriage. His stepsister Kathryn (Sarah Michelle Gellar in second team-up with Phillippe after ‘I Know What You Did Last Summer’) does not think he can pull it off, and offers a wager: if he loses, Kathryn wins his prized car. If he wins, the prize is something he’s always wanted - her. As Sebastian courts Annette – and falls for her in the process – Kathryn sets her sights on ruining the life of simple and sexually naïve Cecilia (played to comic perfection by Selma Blair, ‘Hellboy’), who her ex has dumped her for. The mantra “keep your friends close and your enemies closer” becomes Kathryn’s weapon of choice, befriending Cecilia to plant promiscuous ideas into her head, and pretending to bond with her over activities such as teach her how to kiss. Yeah, you know the scene.


Perhaps what makes ‘Cruel Intentions’ so enduring is its reckless abandon; it’s a walk on the wild side, the kind of film that you didn’t want your parents to know you had seen because, like me, you were most likely too young upon your first viewing. It is unapologetic in its sexuality and, much like the characters themselves, we wait for shit to hit the fan as everyone gets what’s coming to them.

It is interesting to see how my perspective has changed over time too. In a landscape unfortunately dominated by countless allegations of Hollywood sexual abuse and the #metoo movement, much of ‘Cruel Intentions’ feels incredibly unsettling in 2019; gay characters are verbally taunted and blackmailed, the pursuit of sex takes on a hunter-and-prey vibe, and to say that Cecilia is taken advantage of by Sebastian is to put it lightly. Sure, the taboo nature of these characters’ activities is what draws so many people to this film to this day, but there doesn’t seem to be a truly redeeming arc for any character. Sebastian dies after a brawl over his deflowering of Cecilia ends in him being hit by a car. Kathryn’s drug habit and manipulation of her peers is exposed. Cecilia becomes a mistreated plaything by the step-siblings, no doubt earning herself the title of town whore. Annette loses her first love (but at least manages to get the last word in against Kathryn).

Perhaps what makes ‘Cruel Intentions’ so enduring is its reckless abandon; it’s a walk on the wild side, the kind of film that you didn’t want your parents to know you had seen.

There is, however, one scene that stands out. Gellar shines as Kathryn calls out a sexual double standard still present to this day: Sebastian is considered a legend for his sheer number of sexual conquests, yet Kathryn is demonised for hers: “God forbid I exude confidence and enjoy sex... I am the Marcia fucking Brady of the Upper East Side,” she laments. Is it enough to redeem her? Probably not, but to the audience Kathryn is no longer just a heartless bitch who does what she wants just because she can.

Much like other teen cult classics of the 90s, ‘Cruel Intentions’ features multiple scenes where a popular song is prominently featured, making sure audiences are taken back to this film any time they hear it. Perhaps the most famous of these is the use of ‘Bittersweet Symphony’ by The Verve in the film’s closing scene, a song that producers struggled to get the rights for but knew nothing else would fit the scene as perfectly. They were right.

While the film was critically panned, it was unsurprisingly a box office success. No doubt desperate to profit off this, a second (featuring a young Amy Adams) and third instalment in the series were green lit – neither of which featuring the original cast. Both were met frosty receptions and were straight-to-DVD releases. The film has also spawned a musical spinoff and failed television reboot. ‘Cruel Intentions’ may not have aged well with its questionable attitudes towards manipulation through sex, but its juiciness, iconic moments and trailblazing mark it left on the teen film landscape (where do you think Regina George’s Burn Book came from?) makes it an essential watch to this day.

RELEASE DATE: 05/03/1999
RUN TIME: 01h 37m
CAST: Sarah Michelle Gellar
Ryan Phillippe
Reese Witherspoon
Selma Blair
Louise Fletcher
Joshua Jackson
Eric Mabius
Sean Patrick Thomas
Christine Baranski
Alaina Reed Hall
DIRECTOR: Roger Kumble
PRODUCER: Neal H. Moritz
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