In an era of squeaky clean teen movies, Cruel Intentions – released 20 years ago this week – was a sexy cinematic firebomb, one dressed up in a blood-red bustier and dripping in quasi-incestuous dirty talk. A hotbed of elegant townhouses, preppy fashions and lurid camp, Roger Kumble’s Nineties classic feels both entirely of its time and yet oddly ageless.
Inspired by the 18th century novel Les Liaisons dangereuses, Cruel Intentions saw Sarah Michelle Gellar cast as the scheming New York debutante Kathryn Merteuil, a ruthless schoolgirl with a cocaine-stuffed crucifix strung around her neck and an equally nasty stepbrother, Sebastian Valmont, played by Ryan Phillippe. To get their kicks during a tedious Manhattan summer, they set a wager: if Sebastian is able to deflower the dewy, righteous socialite Annette Hargove (Reese Witherspoon), Kathryn will sleep with him in return. If he fails, she’ll get his car.
Beloved by generations of fans for nearly two decades, it’s somewhat unexpectedly rode a second wave of attention during the past two years, where it’s spawned a television sequel, a wildly successful jukebox musical in the US, and a hip-hop mixtape that bore its title. It’s subsequently led many to wonder just how and why it’s earned such a striking legacy.