Chasing Amy (1997)
Ethan Suplee - Desert Blue (1998)
Ben Affleck - Dazed and Confused (1993)
Casey Affleck - The Assassination of Jesse James by the Coward Robert Ford (2007)
Jason Lee - Dogma (1999)
Dwight Ewell - Party Girl (1995)
Joey Lauren Adams - Mallrats (1995)
Guinevere Turner - American Psycho (2000)
Carmen Llywelyn - Never Been Kissed (1999)
Matt Damon - Mystic Pizza (1988)
Welker White - Dead Poets Society (1989)
Ernest O'Donnell - Clerks. (1994)
Brian O'Halloran - Clerks II (2006)
I'm almost positive that this is my second-favorite Kevin Smith movie (Clerks - obviously). It's about comic book artist Holden (Ben Affleck) who falls in love with fellow comic book artist Alyssa and is undetered by the fact that she is homosexual. With perseverance, he succeeds in winning her heart, surprise! The catch comes when he learns more about the sexual misdeeds of her past, and is unable to accept her for her past. The irony is not lost on the supporting characters, who altogether scold Holden for rejecting the woman he loved because he couldn't condone the person she had been, even though she had completely changed herself to be with him.
The difficult question that always sticks with me after I watch this movie is whether Holden is supposed to be a villain or not. Of course you could say that in true Kevin Smith form there aren't any real villains (except in Dogma) but only these schlubby man-children trying to establish a coherent purpose as they bumble through their mundane lives punctuated only by comic book references and the recollections of women they've banged in the past (but rarely turn up in the course of the movie-story itself). But I repeat the question: is Holden an unlikely hero for winning Alyssa's heart and then tragically losing it, or is he a villain for discarding her hard-won affection?