Chasing Amy is far and away Kevin Smith’s best film, and not coincidentally his most heartfelt. I think Smith’s achievement is to tell a universal guy’s story while still featuring significant and sympathetic female characters. Yes, Chasing Amy is spectacularly profane and the characters are prone to giving extended on-the-nose speeches perfectly explicating their inner motivations, but the central theme is worthy and true: love can be a mixture of elevating another to a height to which you can’t measure up, while paradoxically needing to have them do the same to you. More literally, Holden (Ben Affleck) feels both fascinated and threatened by what he perceives as Alyssa’s (Joey Lauren Adams) more adventurous and worldly sexuality, but also needs to believe that he has power over her and has somehow tamed her.
Out of Smith’s oeuvre, the closest to Chasing Amy is Jersey Girl. But his personal meditations on fatherhood required more of his trademark raunch to offset the treacle than the PG-13 allowed. It did, however, feature the single cruelest joke I’ve ever heard: Andrew Lloyd Webber is “the second-worst thing that’s ever happened to New York City.” Zing! Nobody, not even Lloyd Webber, deserves that.
A far better writer than I has already been here and done that: please refer to Matthew Dessem’s review on The Criterion Contraption. I disagree with his obvious dislike of the film, but every point he makes against it is fair.