Dangerous Liaisons on the Upper East Side: 25 Years of Delicious Cruelty

Posted on March 5, 2024

by Eric P

Exactly twenty-five years ago the world was graced with the release of the film Cruel Intentions, a Hollywood movie that took a sordid and scandalous 18th-century French novel about sex and depravity and recast it with spoiled rich American high school students, because it was 1999, and people made weird decisions. Maybe we can blame Y2K.

The novel Les Liaisons Dangereuses was about two rival ex-lovers who compete with each other to ruin other people’s lives for fun. France hadn’t invented soccer or cycling or Jerry Lewis yet so they had to pass the time somehow. The novel’s fans say it’s a savage takedown of the pre-Revolution aristocracy’s corruption, though the fact that Marie Antoinette liked the book a lot makes one wonder. But audiences love stories about bad people behaving badly, so the book was adapted multiple times – in Christopher Hampton’s popular play Dangerous Liaisons, which ran in London and on Broadway with Alan Rickman as the main scoundrel; and then as a film adaptation of the play, starring John Malkovich, Glenn Close and Michelle Pfeiffer. There was also a French movie version in 1959 and a subsequent one from China in 2012.

But arguably none of these versions made as fun and trashy a meal of the material as Cruel Intentions, starring Sarah Michelle Gellar – at the height of her Buffy fame – as the meanest of mean girls, as well as a pre-Elle Woods Reese Witherspoon as a “paradigm of chastity and virtue and thus the unsuspecting target of other characters’ vicious manipulations. It doesn’t really make sense to graft the sexual politics of Dangerous Liaisons onto a high school setting, and it only works because all the high schoolers are in their 20s with lifestyles that don’t resemble those of any actual teenagers. There isn’t a geometry book or orthodontic retainer in sight; their school must be in the same elite divisional bracket as the kids from Gossip Girl.  All their AP classes are in subjects like Classic Cocktails and Private Jet Etiquette.

The movie’s notoriety springs in part from its genuine and unrepentant sordidness but also from the fact that it came out in the 90s, when people were more easily scandalized. The single most famous scene is one in which Gellar and Selma Blair kiss in Central Park – an ardent, earnest, lingering kiss in close-up that won the “Best Kiss” award in that year’s MTV Movie Awards. It’s an iconic moment that’s been parodied and recreated many times since, sometimes by Gellar and Blair themselves. But it also made a splash at the time in part because same-sex connections were still considered fairly rare and exotic in the sheltered and puritanical climate of the mainstream media.

And the film’s pop cultural afterlife doesn’t end there. When Gellar appeared in the 2022 movie Do Revenge, her character – a prep-school principal – was conceived by writer-director Jennifer Kaityn Robinson as a grown-up version of her Cruel Intentions character. Can a reunion movie be far behind?

Les Liaisons Dangereuses by Pierre Choderlos de Laclos

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Les Liaisons Dangereuses by Christopher Hampton


Cruel Intentions: Music From The Original Motion Picture Soundtrack

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Les Liaisons Dangereuses (1959)


Dangerous Liaisons (Wi-heom-han gyan-gye), 2012


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