Chasing Amy

Kevin Smith's quirky charmer features an early-career Ben Affleck as the comic-book artist who discovers the girl of his dreams is a lesbian.

Holden (Ben Affleck) and Banky (Jason Lee) are an inseparable comic-book writing duo, whose world is upended by the arrival of Alyssa (Joey Lauren Adams) on the scene. An achingly hip and gorgeous graphic novelist, Alyssa seems to be the girl of Holden's dreams, if only she weren't a lesbian. While desperately falling for her, he also manages to put his best friend's nose out of joint. Satisfying all these conundrums will be a severe test of Holden's hitherto untapped sensitivity.

Kevin Smith's most mature film is postmodern and progressive (for its time) but at its heart is also a conventional and charming romantic comedy. While its sexual politics may date the film, for its time its remarkably enlightened considering its straight male writer-director. But it's Smith's perfectly pitched comic script that makes it memorable, which balances his penchant for stoner goofiness with a newfound Woody Allen-style sophistication that he's never bettered.