Chasing Amy - 1997
After a pair of films about hipster slackers, the work of writer-director Kevin Smith matured and gained critical respect with this low budget, independent comedy-drama about love, sex and the fine line between the two. Ben Affleck stars as Holden McNeil, a New Jersey comic book writer who is roommates with his best friend and professional partner, artist Banky Edwards (Jason Lee). Their hit comic book series, "Bluntman and Chronic," is loosely patterned after a pair of acquaintances, Jay (Jason Mewes) and Silent Bob (played by Smith), two characters already familiar as supporting players in several Smith films. Into Holden's life comes Alyssa Jones (Joey Lauren Adams), a lesbian and fellow comic book creator who quickly becomes a close friend, although Holden is powerfully attracted to her. Eventually, Alyssa realizes that she is attracted to Holden as well and they begin a physical relationship, much to the consternation of Banky, whose ire over losing his best friend to a lesbian seems to border on romantic jealousy. After he learns something about Alyssa's sexual past, however, Holden's immature response to his new knowledge destroys both his romance with Alyssa and his friendship with Banky. Chasing Amy (1997) was the third film in what Smith referred to as his "New Jersey series," films set at least partly in the Garden State and featuring the Jay and Silent Bob characters.