Cult classic movies often become fan favorites years after their initial release, and the 1999 film Cruel Intentions celebrated another anniversary, having premiered 27 years ago to the day. Ryan Phillippe, Sarah Michelle Gellar,Reese Witherspoon, and Selma Blair cemented themselves in the Hollywood spotlight with the teen romance drama.
In the late 90s, Phillipe and Gellar were already at the forefront of their careers, having both starred in the horror classic I Know What You Did Last Summer, and Gellar starring in Scream 2, All My Children, and the infamous Buffy the Vampire Slayer. Blair and Witherspoon were still up-and-coming actors, with Witherspoon having gotten recognition for her role in Fear a few years before.
Cruel Intentions is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses, and was set in New York City among the elite and high schoolers. It started as an independent film, with the cast receiving praise and making $75 million at the box office.
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It focuses on wealthy teenager Sebastian Valmont (Phillippe), who's notorious for secuding woman for her own personal amusement. He sets his sights on the daughter of his new school headmaster and makes a bet with his stepsister. If he loses, she gets his vintage Jaguar, and if he wins, he finally gets to sleep with his stepsister. The film soon creates a manipulative story that turns a bet into unexpected true love.
Among critics, Cruel Intentions received mixed reviews, but its future cult classic status led it spawn a media franchise. A prequel was released in 2000, and later a standalone sequel in 2004. In 2015, a jukebox musical was developed, and an Amazon TV series was developed in 2024.
The movie also became known for Witherspoon and Phillipe having already been dating during the filming of the movie. They met in 1997 at her 21st birthday party, married in 1999, and divorced in 2006.
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