Alex Austein’s review published on Letterboxd:
An unlikely film from that Kevin Smith.
This was a surprise, because though I knew it was acclaimed, I hadn't ever been a Kevin Smith fan. In CHASING AMY, the air is different, but it doesn't seem that way at first; its cast is composed of the usual crew: Affleck, Lee, Jay & Silent Bob (ugh), but with an unprecedented, encompassing sense of maturity. For years, I've admittedly scoffed at Smith's works, passing him off as degenerate, slob humor, but here in CHASING AMY, he practically feels like a revelation. Ben Affleck in particular delivers a career best performance with his relationship with Joey Lauren Adams being central to the plot, and also shockingly, intensely emotional.
The crudeness inherent to CHASING AMY's stylistic DNA persists, but strangely, it works here. Where in future Kevin Smith films the idiocy would feel so rampant as to be suffocating, the long conversations and monologues here, in all their inarticulateness define and shape these characters. There's a sweeping sense of nostalgia to the film that in its best moments acts like a blunt force. Above all, CHASING AMY captures people that feel and act like believable people in a set, prized era. The bemoaning and emotional strife of Holden and his co-comic creator/best friend Banky are context-appropriate and, in turn transfixing. The range of Adams' Alyssa, culling from a depth of human vices as well as unequivocal joy to deliver on a character at once capable of dense pain and unremitting liveliness is likewise impressive.
It's a testament to the writing quality here that in any of its several-minute long shouted, cried, or screamed discourses Smith evokes the likes of Gordon Green, Linkater, and Allen. Where CHASING AMY is genuinely moving (read: most of its duration), it demands creedence. The film asserts itself, seemingly aware of its skeptics, and then defiantly establishes its own ethos over a brisk 113 minutes that never enters into a lull. The long talks unpacking gender identity, sexuality, and 'standards' feel classic instantly; the grappling exchange of ignorance, experimentation, and secrets; the pulse of defense mechanisms and insecurities...
A potentially timeless flick that'll make you grimace and feel woozy more than actually laugh. A strictly unconventional relationship, without the most ideal payoff. A tremendous effort, and a career best for all involved.