It's been 20 years since Cruel Intentions premiered in theaters on March 5, 1999.
The film follows two vicious step-siblings, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), who attend an elite private school in Manhattan. Drama ensues when Kathryn bets Sebastian that he can't deflower the new headmaster's daughter (Reese Witherspoon) before the start of the term. If Kathryn wins, she gets his vintage Jaguar XK140. If Sebastian wins, Kathryn says she'll sleep with him.
Cruel Intentions is a modern-day adaptation of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses.
Despite receiving mixed reviews, the film earned $75 million worldwide and became a fan favorite, spawning two sequels, neither of which starred the original cast, and an off-Broadway musical. Gellar, Witherspoon and co-star Selma Blair even took in a 2015 performance of the Cruel Intentions musical in Los Angeles.
To celebrate the film's 20th anniversary, Cruel Intentions will return to theaters for a one-week engagement on March 22.
Read on to see what the cast has been up to since their days of high-school scheming.