Chasing Amy (1997)

Holden and Banky are comic book artists. Everything's going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.

Director: Kevin Smith

Cast: Ben Affleck, Joey Lauren Adams, Ethan Suplee, Scott Mosier, Jason Lee, Casey Affleck, Dwight Ewell, Guinevere Turner, Carmen Llywelyn, Brian O'Halloran, Matt Damon, Alexander Goebbel, Tony Torn, Rebecca Waxman, Paris Petrick, Welker White, Kelli Simpkins, John Willyung