Chasing Amy

Chasing Amy (Criterion #75). 1997 View Askew Productions & Miramax Films.
Starring: Ben Affleck, Joey Lauren Adams, Jason Lee, Jason Mewes, Kevin Smith, Scott Mosier, Matt Damon, Brian O'Halloran
Director: Kevin Smith
Buy Chasing Amy at Amazon.

Kevin Smith jokingly referred to Chasing Amy as his "science fiction" movie on An Evening With Kevin Smith, and went on to say that if you asked a lesbian, the events in this movie would never happen in real life, even if, and probably especially because of Ben Affleck.

Anyway, Holden McNeil (Affleck) and Banky Edwards (Lee) are two New Jersey-based comic book artists and lifelong best friends who just happen to share names with characters in The Catcher in the Rye. Things are going great for them up until they go to a comic book convention in New York to promote their comic Bluntman and Chronic. They meet a lesbian-identified young lady named Alyssa Jones (Adams). Holden is instantly attracted to her, despite her sexual identity, and they develop a deep friendship, to Banky's chagrin. Holden falls in love, and one night, he is unable to contain his feelings for Alyssa. She at first considers her confession unfair and inconsiderate since she identifies as a lesbian, but they form a romantic relationship that night. After finding that they had slept together one morning, Banky starts investigating Alyssa's past, and it turns out she has been involved with other men before, as well as a threesome during high school. Holden is deeply disturbed by this, and they argue about it at a hockey game.

Holden has lunch with Jay and Silent Bob (Mewes & Smith), and Bob breaks his silence, relating a long story (peppered with Jay's characteristic insults) about how he was in a similar relationship to Holden and Alyssa. Bob was in love with a girl named Amy, but he was insecure about her past sexual experiences, and that caused him to sabotage the relationship. Silent Bob is angry about letting her go, and he has spent a lot of time since then "chasing Amy". Inspired, Holden dreams up a crazy idea to fix his relationships with Alyssa and Banky: a threesome. Banky is initally disgusted, but agrees, while Alyssa flatly turns him down and walks out of his life. Banky, relieved that there would be no threesome to take part of, does the same.

A year later at a new convention, Holden and Banky are at another convention, separately promoting their latest comics, and Alyssa happens to show up. With some encouragement from Banky, Holden approaches her, and they have a brief conversation. Holden gives her a copy of Chasing Amy, his new book based on their failed relationship.

Recommended, although I'm not entirely sure why it's in the Criterion Collection, apart from the fact that it was a Criterion laserdisc during the '90s before DVDs became hugely popular. Oh well, it's not a major issue.

P.S. What's a nubian?