Director: Amy Heckerling
Stars: Alicia Silverstone, Stacey Dash, Paul Rudd, Brittany Murphy, Donald Faison, Elisa Donovan, Breckin Meyer, Jeremy Sisto
Lesson Learned: Daddy's trust fund can't buy you love.

Don't ever say that you can't fuck with a Jane Austen story. A modernized take on the classic 19th century novelist's Emma, Clueless is the original version of MTV's The Hills, except that it's hilarious, irreverent, fresh, and not full of airheaded fame whores.

It's your basic coming-of-age story set in Beverly Hills, circa 1995, and centers on a pampered rich girl, Cher (Alicia Silverstone, killing it throughout), whose vain existence lacks the love of a boyfriend. She tries seducing the new kid in school, who turns out to be a gay James-Dean-wannabe; then, she gets sexually harassed by an arrogant male friend. That she ultimately ends up with her half-brother (Paul Rudd, pre-fame) is an incestuous resolution that's never questioned.

Not that it needs to be, either. Clueless isn't notable for its plot—it's a '90s classic due to the bubbly characters, winning performances, and hip (for its time, at least) script. And for making grown men want to scream every time a Cher-inspired girl said, “As if!” back in '95.