Cruel Intentions was a 1999 masterpiece about love, betrayal, and Sarah Michelle Gellar making out with Selma Blair. Mostly, it was about an unlikely and profoundly damaging romance between Annette Hargrove (Reese Witherspoon) and Sebastian Valmont (Ryan Phillippe) — gaining chemistry from the pair's real-life relationship.
The premise, for the uninitiated, was this: Sebastian and his step-sibling Kathryn Merteuil (Sarah Michelle Gellar) are upper-class New York City private school kids with a shared interest in sexual mind-games. They team up to corrupt both the super-chipper Cecile Caldwell (Selma Blair) and abstinence poster-child Annette, but make the latter more interesting with a super-creepy wager: If Sebastian has sex with Annette, he gets to have sex with Kathryn. If he doesn't, Kathryn gets Sebastian's fancy, vintage car.
Things go awry when Sebastian starts actually for-realsies falling in love with Annette. Meanwhile, Kathryn does a lot of drugs.
Based on the 1782 play, Les Liaisons dangereuses, Cruel Intentions followed a widespread '90s trend of basing teen movies off classical literature. (See also: 10 Things I Hate About You, Clueless, She's All That.) We're not sure if the film renewed any interest in reading 18th century French literature, but it sure piqued our interest for getting hot and heavy with Ryan Phillippe.