Kevin Smith wrote and directed this 1997 movie, which managed to incorporate his love of comics and geekdom while still delivering a somewhat standard romantic comedy. Ben Affleck stars, before he was one, as a comic book writer who falls in love – with a lesbian, played by Joey Lauren Adams. Check out the casting here, because it’s impressive. Both Affleck and Matt Damon are here, before breaking out as the writers and stars of Good Will Hunting. Both Jason Lee and Ethan Suplee are here, before reteaming by playing brothers on the NBC sitcom My Name Is Earl. And both Jason Mewes and Smith are here, respectively playing the characters they would play in several other of Smith’s movies: Jay and Silent Bob.