Rafi Krespin’s review published on Letterboxd:
Chasing Amy is Kevin Smith’s most personal movie, with its central romantic pairing was based on his previous relationship with Joey Lauren Adams, as well as his incapability of coming to terms with her past. So, the scene where Smith gives his longest ever Silent Bob monologue is essentially him pontificating to a past version of himself that happens to be played by a young Ben Affleck in incel mode. There are other parallels, like Holden (Affleck) lamenting the fact that he wants to write more significant comics than stoner-themed superheroes, just like Kevin Smith wasn’t feeling so great after he made the studio film Mallrats, which was critically-derided and barely made back 1/3rd of its budget.
One thing that was pretty novel for this 1997 romcom was its inclusion of well-realized LGBT characters in Alyssa (Adams) and the African-American artist Hooper X (Dwight Ewell). To the film’s credit, neither Alyssa nor Hooper die or suffer any great tragedy. Especially in comedies, I think an LGBTQ character is well-represented when they are making the jokes and not just the butt of jokes. But while Hooper and Alyssa are fantastic characters, every other aspect of Chasing Amy fails. Every other line in the script has some sort of homophobic pejorative. The inane questions about how lesbians have sex definitely betrays Holden and Banky’s (Jason Lee) ignorance as mere Catholic boys from suburban New Jersey (like Kevin Smith himself), but more importantly just take up too much screen time.
The fact that a homophobic inker from New Jersey and a lesbian slice of life comic specialist believe that straight and gay/lesbian are the only two ways you can swing hints at Smith’s thoughts on this in the 90s. Chasing Amy has a disappointingly dualistic view of sexuality, and that is its largest issue. You’re either gay/lesbian or straight, and there is no spacr for nuance without derision from your friends. No one in the film, including the “sexually enlightened” Alyssa, Hooper, and Alyssa’s lesbian cartoonist pals, mentions or acknowledges the existence of bisexuality or pansexuality in the film, even if it may alleviate some of the tension between Holden, Alyssa, and Banky.
But despite its uninformed and outmoded views on the LGBTQ community and sexuality as a whole, Chasing Amy remains somewhat refreshing as a romantic comedy because it doesn’t settle for a tacked-on happy ending, and its characters do deal with the consequences of their actions.