Chasing Amy (1997)
★★½ — Chasing Amy (1997)
By the mid-1990s, Kevin Smith had already made a name for himself as one of independent American cinema's more distinctive voices. His debut, Clerks (1994), was made on a shoestring and became something of a calling card for a generation of low-budget filmmakers who wanted to prove that sharp, character-driven writing could do the work that expensive production values usually get credit for. Mallrats (1995) followed, and while it found a warmer audience on home video than it did in cinemas, it cemented Smith's reputation as someone with a very particular comic sensibility and a very loyal fanbase. Chasing Amy, released in 1997 and produced through his own View Askew Productions in partnership with Miramax, felt at the time like a step forward, a more emotionally serious film than anything he had attempted before. It won the Independent Spirit Award for Best Screenplay and earned Joey Lauren Adams a Golden Globe nomination, which gave the film a profile well beyond what its modest budget might otherwise have attracted.
The premise is straightforward enough: Holden McNeil (Ben Affleck) and Banky Edwards (Jason Lee) are best friends and collaborators on a successful comic book series. When Holden falls for a fellow comic artist named Alyssa Jones (Adams), he discovers she is a lesbian, which does not, as it turns out, put an end to his feelings. The film takes that setup and tries to do something genuinely thoughtful with it, examining jealousy, sexual identity, and the way men sometimes struggle to separate love from possession. Smith drew on personal experience when writing the script, and that sense of something confessional and unguarded runs through the whole picture. Affleck, at this point still a few years away from the mainstream blockbuster work he would become better known for (you can see where he was heading with Armageddon the following year), gives a performance that relies heavily on his natural ease and likeability. Adams, meanwhile, carries a good deal of the film's emotional weight, and her work here remains the most talked-about element of the production. Jason Lee, familiar from Mallrats, brings his usual sardonic energy to Banky, and Jason Mewes makes an appearance as Jay, one of Smith's recurring figures.
The film arrived at a moment when independent American cinema was at something of a creative peak, with Sundance alumni regularly crossing over into broader cultural conversation. Chasing Amy fitted that mood, presenting itself as a frank, grown-up romantic drama that happened to share its universe with stoner comedy and comic book culture. Whether it fully delivers on that ambition is, of course, the question.
It just feels a little weird? Kevin Smith movies are always a bit of a mixed bag, and Chasing Amy is no exception. There's definitely an entertaining, heartfelt story buried in here somewhere and when you're younger, it all feels very raw and "real." But watching it now, it just feels messy. The dialogue is so unnatural, the characters often act in ways that don’t make any real sense, and the whole thing is a little too immature to fully land. It’s got its moments, and Smith’s heart is clearly in the right place, but like a lot of his work, it just hasn’t aged particularly well.
I think that tension between ambition and execution is what stays with me most. There are scenes in this film that clearly meant a great deal to Smith when he wrote them, and you can feel the sincerity behind them, but sincerity only gets you so far when the scaffolding holding everything up is this shaky. For all its good intentions, Chasing Amy ends up being one of those films you appreciate more as a document of a particular moment than as a piece of storytelling that holds together on its own terms. If you want Smith working closer to his strengths, his broader comedic work scratches a different kind of itch. But as an insight into what he was reaching for, it's worth a watch. Just maybe don't expect it to hit the way it once did.
Rating: ★★½ | Year: 1997 | Watched: 2025-04-27
Trailer
▶ Watch the official trailer for Chasing Amy (1997) on YouTube
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Related on Movies With Macca
More from Kevin Smith: Jay and Silent Bob Reboot (2019) · Jay and Silent Bob Strike Back (2001) · Mallrats (1995) · Clerks (1994)
More with Ben Affleck: Daredevil (2003) · Good Will Hunting (1997) · Gone Girl (2014) · Armageddon (1998)
More from the 1990s: Lessons of Darkness (1992) · Shinjuku Boys (1995) · Blue (1993) · Cemetery Man (1994)
More comedy: The Eagle (1925) · The General (1926) · Americana (2023) · The Naked Gun: From the Files of Police Squad! (1988)
More drama: Viy (1967) · Wonder (2017) · A Better Tomorrow (1986) · Beautiful Boy (2018)
