Kevin Smith isn’t exactly known for being sensitive, given his propensity for swearing and graphic descriptions of sex acts, but the beloved indie filmmaker actually has a couple of top-tier romantic comedies under his belt, one of which is the criminally underrated Zack and Miri Make a Porno (don’t let the title put you off). The other, naturally, is Chasing Amy, Smith’s 1997 follow-up to Mallrats and his last-ditch attempt to convince the movie industry that Clerks wasn’t a fluke. Weirdly, Mallrats has way more in common with the Jersey native’s celebrated debut – even though Chasing Amy is loaded with references to what fans now recognise as the View Askewniverse. Otherwise, it’s a stripped-down and unflinchingly frank depiction of a fragile male ego in turmoil that was notably inspired by Smith’s own insecurities. 

The whole comic-book industry angle suggests this is boys’ stuff, but once that framework has been established, Smith gets to work turning his attention to the spiky burgeoning romance between hapless Holden (a charming, and never more naturalistic Ben Affleck) and out-and-proud lesbian Alyssa (a luminous Joey Lauren Adams) – whom the scene-stealing Hooper X (Dwight Ewell, who gets all the best lines including a hilarious Star Wars takedown) lovingly describes as a “pile of PMS.” At first, Holden plays it cool by shrugging that Alyssa is only “all right,” but it’s obvious from the very first moment he lays eyes on her that he’s smitten. His eyes widen and shine, his shoulders relax, and Holden focuses every ounce of attention on Alyssa – which pays off massively in one of the film’s funniest sequences, as Holden goofily dances in the crowd, assuming Alyssa is singing to him rather than the woman standing right next to him.

Smith clearly knows the rom-com genre intimately; Chasing Amy hits all the classic beats from the rambling and cringe-worthy declaration of love to the kiss in the rain, the big argument, and the eventual fallout. Crucially, the writer-director doesn’t force Holden and Alyssa together at the end, making a compelling case for them as a couple without necessarily confirming whether it would be the smartest move for either party. The chemistry between Affleck and Adams is palpable, which makes the inevitable denouement completely devastating even though we know it’s probably for the best. Happily, in Jay and Silent Bob Reboot, Smith revisits both characters, revealing they’ve had a baby together but aren’t romantically involved. The moment also allows him to tackle some of the biggest criticisms Chasing Amy has faced in the years since its release, particularly the movie’s alleged handling of a straight man “turning” a lesbian.

In “Kevin Smith’s Secret Stash: The Definitive Visual History,” the writer-director clarifies that his “intention wasn’t to make a gay film.” As Smith explains of his idea for the premise: “A guy falls in love with a lesbian and they are great together, but he falls prey to his own bullshit and male sexual insecurities.” In fact, the filmmaker based it off his own relationship with Adams, which was beset by issues over her sexual past. Chasing Amy was Smith’s attempt to make amends, while also giving the actor a proper showcase for her talents (side note: WTF happened to Adams’ career? She should’ve been huge). Regardless, suffice to say the LGBTQ+ community doesn’t hold Chasing Amy in particularly high regard, which is funny considering Alyssa’s lesbian friends immediately turn on her when she starts dating Holden. But what if she’s just bisexual? We learn over the course of the movie that Holden isn’t the first man Alyssa has been with, which is a major component of why he ultimately fails to make things work with her. And, with each year that passes, the movie increasingly feels like a suitably chaotic bi love story.

In Reboot, Holden admits that if Chasing Amy were made today, the story would have to be told from the perspective of anybody but a straight, white male. That may be true, but Alyssa isn’t shoved to the side here – far from it since Smith envisioned his movie as a love letter to Adams and based the character on her. Although it’s obviously valid to feel affronted by any suggestion that someone can be turned, that’s not the argument Chasing Amy is making. Rather, this is a story about how sexuality is fluid, and we can’t always choose who we fall in love with, as further evidenced by Banky’s unrequited love for his BFF (by Jay and Silent Bob Strike Back, he’s casually sleeping with Hooper). The joke is 100% on Holden whose “boring, funny book-making ass” Alyssa is forced to settle for, as Hooper memorably points out, rather than his magical dick saving her from a life of vaginas. He isn’t necessarily the villain of the piece, but Holden definitely isn’t the hero either. Like most of Smith’s characters, he’s an emotionally stunted, selfish little man-child. However, unlike most of them, Holden is also capable of confronting his own feelings even if it means isolating those he cares about most. 

Such is the real question at the heart of Chasing Amy — what if Alyssa, and indeed even Holden and Banky, aren’t strictly gay or straight, but bi? Bisexuality has been infamously mishandled in pop culture throughout history, but we’re slowly making changes (“slowly” being the operative word). Smith might have been ahead of his time, consciously or otherwise, in how he presents these confusing feelings as they emerge. Chasing Amy has been repeatedly dismissed and denigrated since its release, but there’s more going on beneath the surface than maybe even its creator realised when he was writing it. And it makes more sense when viewed through this lens, especially 25 years later, given our wider modern understanding of sexuality, gender, and everything in between. It’s worth noting, too, that Smith doesn’t approach lesbianism through the drooling lens of a straight man who watches girl on girl porn. There’s a frank, even informative, discussion of lesbian sex early on, while Banky claiming lesbians just need to find the right man is rightfully presented as ignorant, once again negating the idea that this was the real message of the movie.

Holden also criticises his buddy for throwing around slurs like “dyke” and “faggot” years before mainstream media would finally acknowledge they were wrong (The Hangover, which was released in 2009, includes the F word in one of the very first lines onscreen). When he comments that there are “a lotta chicks in this place,” again we’re supposed to laugh at his cluelessness. And finally, when Banky pushes Holden to the brink, leading his friend to loudly declare that he’s “f***ing in love with her, man, okay?!“ It’s another example of how little he understands romantic relationships. Banky is consistently the one in the wrong, rather than Holden or Alyssa, whose great crime is falling for each other when they’re not supposed to. That’s what makes his big “I love you” revelation so powerful; it’s messy, uncomfortably real, and totally embarrassing. Meanwhile, Alyssa is understandably hurt that he’s put her in the position of having to reiterate where she stands. And yet, “If this is a crush, I don’t think I could take it if the real thing happened” is such an un-self-consciously romantic line that it’s tough to imagine how anyone could resist.

Affleck is such a natural, charismatic performer and the role of Holden fits him like a big duffle coat, but Adams is so sexy in Chasing Amy, and Smith shoots her so lovingly, it’s obvious to everybody watching why he falls so hard for her. The actor looks effortlessly cool, clad in tomboyish T-shirts and oversized jackets, and typically going braless – emphasizing how little she cares about the opinions of men. But Smith takes his time establishing a genuine connection between Alyssa and Holden so there’s no confusion about why he’s attracted to her. “It’s not who you love, it’s how” went the film’s tagline and it’s true that, in the end, Alyssa’s sexual orientation doesn’t matter as much as the fact she’s simply lived a bigger life than Holden. They might not be right for each other, but their relationship brings out something special in both Holden and Alyssa. Moreover, considering the proliferation of incels and MRAs nowadays, it’s comforting to know that almost 30 years ago Smith not only recognised but shrewdly skewered the idea of a man who was so intimidated by the woman he fancied that he ruined their relationship.

Chasing Amy has understandably aged since its release. It’s jarring to see people smoking indoors, and the score can be overpowering at times – Smith is confident enough to let scenes breathe nowadays – but it remains one of the prolific filmmaker’s most emotionally honest works. Powered by two equally great lead performances, it’s a funny and swoon-worthy rom-com in its own right – the fight in the rain is an all-timer for the genre – but as a piece of queer culture, it deserves to be reassessed, particularly by younger LGBTQ+ viewers. Maybe we’ve waited all this time for a bi love story that was right in front of us, much like Holden and Alyssa themselves. 

by Joey Keogh

Joey Keogh is a freelance writer from Dublin, Ireland with an unhealthy appetite for horror movies and Judge Judy. In stark contrast with every other Irish person ever, she’s straight edge. Her favourite movies include 10 Things I Hate About You and Scream, but defending Queen of the Damned is fast becoming her vocation. She tweets, mostly about “feminism and hating Ed Sheeran,” according to her little sister, at @JoeyLDG. Hello to Jason Isaacs.