Cult favorite Cruel Intentions turned 20 years old last week. The movie was inspired by the 18th-century novel Les Liaisons dangereuses by Pierre Choderlos de Laclos. The novel is about two ex-lovers turned rivals who use seduction as a weapon to control and exploit one another. The cruel games and manipulative talent inspired the 21st-century remake. At the time Cruel Intentions came out in 1999, the world was unprepared for such debauchery. Cinema was in an era of innocent, clean teenage movies and when it came to theaters it exploded.

As far as movies go, the cast is very important and Cruel Intentions is no exception. Sarah Michelle Gellar played Kathryn Merteuil, a scheming New York schoolgirl with a cocaine problem. Her stepbrother Sebastian Valmont, played by Ryan Phillippe, is just as manipulative as Kathryn. The two step-siblings make a bet: Sebastian has to score big with the daughter of the headmaster at their school, Annette. The thing is, Annette will only wait until marriage to sleep with a man. The deal is that is Kathryn wins the bet, he gets to be with Kathryn, the only girl he will never have. And if he loses, Kathryn gets his Roadster.