Chasing Amy does not exactly hold an esteemed position in the cultural memory. Partly this is because of Kevin Smith’s current station: the director of films no one likes, and the author of the worst tweet ever. But the bigger problem is that its logline makes it sound genuinely offensive: Holden (Ben Affleck) falls in love with lesbian Alyssa (Joey Lauren Adams). And she falls in love with him right back.
This premise was criticized at the time: just a few years later in her cultural history of gay visibility, Suzanna Danuta Walters called Chasing Amy “explicitly a boy’s fantasy about girls who like girls.” But the mists of time have given that critique new teeth. That’s partly because mainstream understanding of the LGBT community has galloped ahead in those twenty-five years, and partly because it’s an easy film to dunk on based on hazy memories of seeing it once. On Last Week Tonight, John Oliver said that “actually watching” Chasing Amy bursts any nostalgia for 1990s indie movies: “Set aside the notion that any lesbian could be magically turned straight if the right guy comes along. What’s extra offensive in hindsight is the idea that guy would be Ben Affleck.” Who, I guess, is a notorious uggo.
But if you do sit and watch Chasing Amy, that’s not what it’s like at all. It’s a genuinely affecting rom-com about characters navigating different roads through sexual identity – none of whom are straight.
Holden is a comic book artist who, with his best friend, roommate, and inker Banky (Jason Lee), makes Bluntman and Chronic: depending on who you ask, it’s like Rosencrantz and Guildenstern meet Vladimir and Estragon, or like Bill and Ted meet Cheech and Chong. He meets fellow comics artist Alyssa at a convention. Holden is instantly smitten; Banky is instantly annoyed.
This becomes their holding pattern. Holden hangs out with Alyssa all the time: bitching about finding Bluntman and Chronic creatively unsatisfying and asking ignorant questions about lesbianism and, occasionally, being cute, witty, and charming. Banky resents Alyssa and her friendship with Holden. He ups his already generous quota of homophobic slurs to yell at Holden about how he needs to stop spending all this time with her. In these early scenes of the film, Holden’s the ally and Banky’s the bigot. Holden tells Banky to stop using the f-slur; Banky screams about how lesbians are man-hating. Which Way, Heterosexual Man? But the rest of the film slowly peels that back, revealing something richer and thornier.
When Holden and Alyssa sleep together, she tells him that he’s the only man she’s ever been with. He finds out that isn’t true from Banky’s yearbook sleuthing – that she slept with two guys at once in high school – and it eats him up inside in a way that Alyssa sleeping with, by her count, “half the women in New York” doesn’t. It’s a concern for sexual purity rooted clearly in a belief that what lesbians do isn’t “real” sex: before they got together, he said she was still a virgin because she hadn’t been “physically penetrated.” Biphobia, slut-shaming and masculine insecurity pushes them apart. She tells him that saying he was the only man she’d ever been with lit him up in a way her saying how special he was couldn’t seem to. If their union plays like a boy’s fantasy of “turning” a lesbian, the truth looks like a bisexual woman knowing appealing to that fantasy is a lot easier than being understood for who you are.
Simultaneously, it’s made clearer and clearer that Banky is in love with Holden. Jason Lee, never better, delivers Banky’s homophobia and misogyny so viciously that it’s incredible he remains sympathetic. His closetedness contextualises his bigotry – the kind of closeted that everyone can see but him. Banky’s homophobia is self-hatred. His dislike of Alyssa is jealousy. “Don’t kid yourself,” Hooper (Dwight Ewell) tells Holden, “That boy loves you in a way that he’s not ready to deal with.”
So when everything is falling apart, Holden presents a solution. He sets a table for three, pulls up a chair in front of Banky and Alyssa, and says they need to have a threesome. He presents it as beautiful resolution to every issue between the three of them: he won’t feel inadequate next to Alyssa’s sexual experience, Banky can “take that leap” that everyone sees he should take, with his best friend and with the reassuring presence of a woman, and all the tension and resentment between the three of them will dissolve.
Banky takes a deep, shaky breath, and says, “Sure.”
Alyssa gives a big, teary speech about why it’s a stupid idea – about how gross it is for Holden to assume that because she’s had a threesome before she would naturally be happy to have this threesome now – then slaps Holden and tells him where to go. “He’s yours again,” she says to Banky on her way out.
“My agenda is to watch your back,” Banky tells Holden the morning after he first sleeps with Alyssa, “To ensure that all this time we’ve spent together, building something, wasn’t wasted.”
“She’s not going to ruin the comic,” Holden replies easily.
“I wasn’t talking about the comic,” Banky says. It’s obvious here – more obvious, even, than it is later when Holden smacks a kiss on Banky’s lips and talks about how they’ve “been everything to each other but intimates, and now, we’ll have been through that together too” – that this was never a movie about two straight guys and a lesbian. 
