Chasing Amy (1997)

Smith's third film in his "Jersey Trilogy" is also his best, a surprisingly mature and thoughtful romantic comedy that is nonetheless true to Smith's distinctive comic sensibilities. It is greatly helped by the performances of Ben Affleck, Jason Lee, and Joey Lauren Adams, who make up the fine ensemble cast. Smith takes a more low-key approach here, avoiding the crude, slapstick comic hijinks of the previous MALLRATS, and expanding on the themes of friendships and romantic relationships that he explored in the earlier CLERKS, creating an insightful and sometimes profound comedy -- and one of the best indie films of the late '90s -- in the process.