Chasing Amy (1997)
Director: Kevin Smith
Stars: Ben Affleck, Joey Lauren Adams, Ethan Suplee, Scott Mosier, Kevin Smith, Jay Mewes
Lesbians, comic book artists, and Jay and Silent Bob aren't exactly what you think of when you hear the term "rom-com," but Kevin Smith manages to put a lasting spin on the simple, often predictable genre.
In Chasing Amy, illustrator Holden McNeil (Ben Affleck) falls for the unattainable yet alluring Alyssa Jones, who also happens to be a self-proclaimed friend of Ellen DeGeneres. Still, their relationship comes to fruition, even as their other (platonic) relationships disintegrate, most importantly between Holden and his BFF and writing partner Banky (Lee).