3. Chasing Amy (1997)
What easily stands as Kevin Smith's most intelligent and mature film also gives way to one of Ben Affleck's most considered and restrained performances, despite the potential lunacy of the subject matter (and the guy directing it). This would mark Affleck's second collaboration with Kevin Smith - after Mallrats - and essentially helped him become the household name that he is today, as Holden McNeil, a comic book artist who falls for a fellow artist (Joey Lauren Adams), who in fact turns out to be a lesbian. Affleck is fortunate enough to be handed a lot of Smith's most thoughtful dialogue to date, delivering a performance that stands as perhaps his most complex; muddled, obsessive, confused, curious, and devastated all at once. The scene in which he and Adams have an argument in the rain is easily the best thing Smith has ever directed in his career, and it's one of Affleck's best moments, too. As an unconventional romantic figure here - given the hilarious and poignant culmination of the "three way" scene - Affleck's Holden might be a hero for forlorn artists everywhere.