9 Movies Featuring BFFs Matt Damon and Ben Affleck

"Chasing Amy," released in 1997, stars Ben Affleck as Holden McNeil, who meets and falls for Alyssa, played by Joey Lauren Adams. But Amy is a lesbian, and Holden can't handle that. Silent Bob (director Kevin Smith) warns him that he was in a similar relationship with a girl named Amy, and he felt like he was always chasing her. Damon also appears in the film as an executive.

"Chasing Amy" is Smith's third movie set in the universe he created with 1994's "Clerks." The indie film became a box-office smash, though many have criticized its portrayal of Alyssa's sexuality and the fact that the movie doesn't use the word "bisexual."