Perfect Movies: Chasing Amy


Movies don’t have to be glamorous affairs of great spectacle and directorial flourishes that astonish the viewer to be perfect. Sometimes a small film composed of all-too-human emotions can speak volumes more than highly concentrated dramatics with people anguishing over unspeakable tragedies. Sometimes it can just be about a young guy who doesn’t know how to navigate the trickier waters of a relationship and ultimately losing out on something potentially great because his sense of  jealousy overtakes any more mature understanding he could resolve instead.

For this kind of film, there may be none more muted and direct than Kevin Smith’s Chasing Amy. Although Smith may not be the flashiest director–and certainly by his own admission not the most refined–at times he’s been able to capture truly unique and sincere situations, whether it be two overworked, underpaid, and increasingly cynical cash register jockeys in his influential debut Clerks or here, in his romantic comedy with an edge and a heart to match, Chasing Amy.


Listen: Kevin Smith has not had the best film career, especially since his first three films in the 1990s showed so much promise. Clerks was an ultra-low budget comedy masterpiece that inspired a generation of filmmakers while Mallrats updated the goofy teen comedy to the 1990’s. His much-overlooked Dogma was a surprisingly complex and mature comedy that uses faith as its vessel. Heck, even the short-lived Clerks: The Animated Series is a small masterpiece in its own right, successfully transferring his original characters Dante and Randall (and of course, living cartoons Jay & Silent Bob) into the animated medium.

Unfortunately, Smith decided to lean into his worst instincts for both his comedies and dramas thereafter: the mindless and ultimately pointless Jay & Silent Bob Strike Back managed to weave bits and pieces of his “Askew-niverse” (named after his production company, View Askew) but otherwise starred his juvenile comedic characters Jay and Silent Bob, whose perspectives–along with their personas and sartorial choices–stopped around the age of 15 when being a stoned slacker hanging out in front of a convenience store was somewhat appropriate. His return to sincerity, Jersey Girl, was overcooked, formulaic thin soup that had little going for it and lacked the balance of humor and heart that his previous success in this mode, Chasing Amy, so deftly captured. Then he did Cop Out, which who cares, and then Clerks II, a tired retread of an old idea that needn’t an update, much less a whole other movie, to wrap up the already limited lives that we  glimpsed in the first picture.

And after that, The Curious Case of Mr. Smith took three more intriguing turns, as he first wrote and directed the hard-hitting, totally unexpected Red State, his bloody and suspense-filled take on American religious extremism, which brought some of the best reviews of his career. And then he made Tusk, a film–no kidding–based on some bullshit spitballing he did on his podcast about a podcaster who is imprisoned by some maniac that forcibly turns him into a walrus. It was bizarre and unexpected, and not his best movie, but at least it’s a vision of him trying something new.

And then he made Yoga Hosers, starring his daughter and Johnny Depp’s daughter, who are pals in real-life, about two girls working a souvenir store at the US-Canada border who have to fight off disgusting monsters one night. It was, you know, terrible. And a lazy effort. And unnecessary.

After this, who knows where Smith heads in his film career? After making a solid comeback with Red State and reinventing himself as a potential force to be reckoned with in the indie world once again, his middling follow-up and outright bomb thereafter seems to show Smith slowly sliding backwards into Director’s Jail.

A Jersey Thing

It’s unfortunate for a number of reasons, mostly because he’s a director that shows real promise with some of his work and is in a position to make any smaller independent film he desires but chooses to chase some money and make a number of calculated missteps along the way.

Personally, and not to break the third wall here, but I live in New Jersey roughly in the same area that Smith set many of his earlier films. When I was younger, his movies spoke to me in a personal way because he was making films I admired in the very same locations that I would drive by or walk past or even enter in real-life. It made the films specifically personal to me, and his most personal film–and I argue his best film–is shot in so many local locales that I often see and am familiar with that it has turned into a small film that seems to play inside of me when I watch it.


That ice rink exterior? That’s in the town over from mine. The location of Banky’s and Holden’s studio and apartment? That’s above Jack’s Music Shoppe in Red Bank, a place I’ve bought from often and even knew some people that have worked there. The Comicon that’s in the movie was shot in the Berkeley Hotel in Asbury Park, a hotel you can’t miss when you’re in town and I’ve even stayed a few times.

The point being, if you’re from New Jersey, you tend to take Smith’s films a little more personally than if you’re from, say, Iowa. His visual vocabulary is so close to the actual world you live in, you almost feel like you’re going to run into his characters while walking down Broad Street in Red Bank or kicking sand on the boardwalk one lonely night. Ironically, Smith’s own comic book store–Jay & Silent Bob’s Secret Stash–is almost directly across the street from Jack’s Music Shoppe, and walking into is also walking into a mini-museum of Smith’s career. There’s Buddy Christ from Dogma hanging out in the back of the shop; you can buy posters of his various movies, some signed; and for sale there’s even a one-sheet replica of the last page of the personal comic book Holden wrote about his relationship with Alyssa in Chasing Amy.

Maybe because it’s his most personal movie to date, or maybe it’s because I take Smith’s work personally on some intrinsic level that I won’t go into here (and probably a lot of both), but for me Chasing Amy is a perfect movie.

Chasing Amy – A Perfect Movie

This very small story centers on Holden, a late 20-something who has found success with his comic book Bluntman & Chronic. Working and living with his best friend Banky, he seems to have made a comfortable life for himself. But while attending a Comicon to promote his work, he meets Alyssa, a cute comic book artist with that he befriends and flirts with afterwards in a bar.


A short while later, they’re invited out for the night by a mutual friend of theirs and Alyssa’s, Hooper X, who writes a Black Power-themed book but hides his homosexuality for image purposes. Holden and Banky go out for the night and Holden again meets up with Alyssa, sure that they have made a connection. But he’s ultimately surprised when he finds out Alyssa’s a lesbian while Banky finds it more than a little hilarious.

But Alyssa likes Holden and she makes an attempt to befriend him. They spend time together and have a good rapport but Holden is falling in love with her. Despite Banky’s insistent warning that Holden is chasing the impossible–calling Holden “the most persistent traveler on the road that’s not the path of least resistance”–Holden eventually reveals to Alyssa his feelings for her. While initially furious with him, she quickly falls into his arms and they begin a tumultuous relationship where both find ostracism from their friends and, for Holden, the nagging tug of insecurity and jealousy pulling away at his potential happiness.

This comes to a boil when Banky–hurt from his partner’s new absorption into another relationship–purposely goes digging for dirt on Alyssa and finds it in the form of stories of Alyssa’s promiscuous past with both women and men. While indelicately prodding Alyssa for information to verify these stories, she explodes on him in public and after a tearful and angry admission, says that’s all in the past and they can be happy now.


Holden, unsure whether his own pride will allow him to come to terms with Alyssa’s wild youth, meets up with the inspiration for the Bluntman and Chronic comic book, Jay and Silent Bob, in a diner to give them their likeness rights check. After a brief conversation about his issues, Silent Bob tells the story of him and his ex-girlfriend Amy, who also had indulged in some sexual adventures of her own before meeting him. And while he rejected her on this basis, Bob says that he was stupid and let his own insecurities stop him from having what could have been a real and substantial relationship–and ever since then he’s been chasing Amy, so to speak.

Holden seems to understand the message of Bob’s story and calls for a sit-down meeting between himself, Banky, and Alyssa. But what he proposes is so completely tone-deaf and wrong-headed that Alyssa slaps him across the face and storms out while Banky quietly walks away.

Cut to one year later at the next Comicon: Banky signs what looks like the last volume of Bluntman and Chronic, letting a fan know that the book just kind of stopped without revealing why as he sees Holden across the room. They wordlessly communicate to each other, but that’s all.

Alyssa, at her table, has a comic book dropped in front of her–but it’s not one of hers. She looks up and sees Holden, who says that this is the comic book he’d been working on, called Chasing Amy. She turns to the last page and sees that the book’s an apology to her. He walks away, she calls for the next person to sign their comic book, and the movie ends.


“This is all gonna end badly.”

First things first, let’s talk about the pink elephant in the room: Alyssa’s sexuality. While this film has caught a lot of flak from the LGBTQ community about how quickly Alyssa seemingly capitulated to a heterosexual relationship, it should be noted that (unbeknownst to both the audience and Holden up to a point) she did have relations with men in her life, which to me seems to categorize her as bisexual. So although Kevin Smith even acknowledged that many lesbians had contacted him that it’s unbelievable a lesbian would “turn” heterosexual, this is not how I read the film: it seems, instead, that she was bisexual, was turned off by men for a long period of time, and then found someone with which she thought she could build a relationship. It wasn’t “turning” heterosexual but exploring another side of her sexuality, one that she had dismissed long ago.

And I wanted to address this before discussing the film further because ultimately this film makes a very earnest effort to give its characters depth and dimension. Alyssa’s not just a lesbian who was suddenly attracted to a man but a bisexual that hadn’t been attracted to a man in a long time–and her standing in the lesbian community is jeopardized as a result.


Just as the late-stage potential revelation that Banky might be gay, and that Hooper X explicitly discusses his difficulty being both a black man and a gay man, Alyssa’s status as a bisexual rather than a lesbian who falls for a straight man gives her character more nuance and shading–and not incidentally, this reading is far less condescending to lesbians in the audience who reacted negatively to the idea of Alyssa as a lesbian who is swept off her feet by a man. Instead, Alyssa’s more conflicted and complex–and her own feelings in the relationship far deeper and more sympathetic–than just assigning her as the “magical lesbian” that goes straight for a guy.

“Archie is not fucking Mr. Weatherbee!”

But to go back to the topic of Kevin Smith once again: the guy’s a good writer. He honestly has a gift for naturalistic and funny dialogue. Although Banky–being the comic relief–gets the more explicitly funny material, every character is pretty funny throughout. Alyssa is at turns both snarky and sweet, Holden’s a little cynical but at least trying to be charming, and Hooper X is an interesting character of his own, being a gay black man in a film in 1997 that isn’t completely camp–instead, he acknowledges his own problems of being “a minority of a minority of a minority.”

And Smith can write a compelling small-scale story: a day in the life of two clerks sounds terrible at first, but Smith gave his characters in Clerks personalities and problems of their own that the audience can invest in just through dialogue alone. While they try to liven up their day by playing hockey on the roof, most of the time it’s Dante and Randall bullshitting about their lives and problems–and it remains interesting because Smith knows how to write.


And with Chasing Amy Smith wrote a genuinely unique romantic comedy without pandering to anybody: Alyssa remains an independent character who puts her foot down; Holden’s clueless until it’s too late, like most guys; and Banky hides a lot of his own frustrations behind a veil of sarcasm. Unlike the “Hollywood ending,” which would see Alyssa and Holden together and possibly married, Smith’s third-act twist was that they don’t end up together and that Holden continues to be wrong. Even the epilogue at the end doesn’t promise anything: Banky’s moved on, Alyssa’s moved on, and only Holden is left to try and make a resolution.

Maybe what makes Chasing Amy so affecting is what made Clerks so impactful: Smith is working on the smallest of scales with only six people as part of the main cast. Clerks was just about two dudes working their boring, shitty jobs. Chasing Amy is just about two people trying to make a relationship work. Through witty dialogue and engaging characters, Smith makes both of these films highly relatable on a human level.

Unlike overblown “wacky” parody comedies like Jay and Silent Bob Strike Back or rehashed, unnecessarily reworked films like Clerks II, or frankly bizarre horror like Tusk, Chasing Amy and Clerks work because they’re not trying to be anything other than what they are: films about the daily small sturm und drang of life. Sure, maybe you never dated a lesbian, but you probably have had the same sort of insecurities about a partner’s past sexual experiences before. And maybe you’ve even screwed up a relationship because of it.

And it’s all very human and relatable. And Smith is at his best when he’s working on this scale with these types of familiar problems–especially when he takes the unexpected route in his storytelling. One reason Jersey Girl fails so spectacularly as a film is because it hits the familiar beats of a well-worn formula that any filmmaker could deliver. But Kevin Smith wasn’t supposed to be just “any” filmmaker–that’s why his audiences liked his work so much to begin with.

“Alyssa: Looks like a very personal story.”

“Holden: I finally had something personal to say.”

There have been so many romantic comedies made in the history of film that they often blur together and become one unrecognizable collection of tropes, formulas, and cliches. Will the clueless guy finally figure out love? Will the unattainable girl finally settle down? Will they all end up happily ever after? The answer to these questions 99% of the time in romantic comedies is, “Of course. Duh. What do you think I paid my money for?”

But Chasing Amy stands out because the answer to all of these questions is “probably not.” And the film’s not being cruel with this denial of a happy ending: after all, Alyssa having agency and the sense not to let Holden dictate her sexual behavior is the appropriate message at the end of the film. In fact, Holden’s left alone at the end by both his romantic and business partner, respectively, because he doesn’t figure out love–and that’s totally OK.


Few romantic comedies would have the guts to deny its audience a traditional happy ending because, well, that’s what the audience paid their money for, after all. But Chasing Amy is perfect in how it provides some damn good reasons not to give the audience its happy ending: because Holden didn’t understand and ultimately says and does the wrong thing to make Alyssa walk away. And while he does seem to finally figure it out, it’s too late and time–and the moment–has passed him by. It may not be the happy ending, but it’s the realistic one–and ultimately a satisfying one. And maybe, for some people in the audience, it contains an important lesson that should be taken to heart.

Chasing Amy is a film that shows you don’t need a large budget, A-list stars, or even a particularly flashy directorial style to make a memorable, sincere film. You just need a solid script, some good actors, and a story worth telling. I believe that Kevin Smith has plenty of talent and a lot of good stories in him–and Chasing Amy is a perfect example of this.

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