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Chasing Amy at 25: A Complicated Work from Kevin Smith 

It’s not who you love. It’s how.

Revisiting Kevin Smith’s Chasing Amy

In some ways, Kevin Smith’s Chasing Amy has a lot in common with Clerks, the director’s breakthrough movie that had arrived three years earlier.

It’s mostly about the friendship of two dudes, who sit around and talk about sexuality and pop culture ephemera. One has a girlfriend, the other doesn’t, and the girlfriend-less guy gets in the way of the relationship. The dialogue is wildly, transgressively raunchy, and there are deep disquisitions about Star Wars and other Smith-flavored nerd culture. 

But Chasing Amy is much different aesthetically- it’s in color, and doesn’t look like it was produced using maxed-out credit cards (its budget, a still-low $250,000, was a tenfold increase over the $27,000 that Clerks cost.) It even starred professional actors. 

More important than that, though, is that Chasing Amy stands as a surprisingly mature work on Smith’s part. Sure, it’s true to the spirit of what the director had made previously, and it’s clearly in his voice. Most notably, it’s a movie about a guy who falls for a woman, behaves irresponsibly, and the movie concludes that he was wrong.

Image: Miramax

Smith had famously followed up Clerks the following year with Mallrats, a notorious flop and critical dud, although Smith and his fans have gone on to reclaim in the ensuing years, and have even talked for years about making a sequel. Chasing Amy was seen as Smith’s attempt at a post-Mallrats comeback.  

Chasing Amy, which arrived in April of 1997 – 25 years ago this week –  starred Ben Affleck and Jason Lee, who were both in Mallrats, as Holden and Banky, a pair of lifelong best friends who work together as comic book artists, drawing a series, Bluntman and Chronic, that’s based on Smith stalwarts Jay and Silent Bob. 

Holden and Banky, unlike the aimless dudes of Clerks and Mallrats, have actually attained some degree of professional success, perhaps a commentary on Smith having himself become a success by that time in his life. But in a very ’90s subplot about “selling out,” they’re considering whether to go along with a plan to make a TV version of their comic books. 

Their friend Hooper (Dwight Ewell), is quite possibly the best, most multi-faceted character Smith has ever written. He’s a gay comic book artist who poses as a Black militant, while at the same time lamenting that he can’t get any respect as a gay man in the era of lesbian chic. Two decades of race-related arguments about Star Wars were anticipated by Hooper’s “Fuck Lando Calrissian” speech. 

The events of the plot are set in motion when Holden meets Alyssa (Joey Lauren Adams, Affleck’s fellow Dazed and Confused alum), also a comic book artist, and is instantly smitten- that is, until he finds out she prefers to date women. They soon become close friends, and then something more, all earning the resentment of Banky, who digs up dirt about Alyssa’s past sexual transgressions with men. 

Kevin Smith films
Image: Miramax

This leads to Holden proposing an unorthodox Hail Mary solution, Alyssa rejecting it (and him) outright, and, as seen in an epilogue a year later, going back to dating women, while it’s also implied that Holden and Banky are no longer friends. Glimpses at the characters in various canonical Smith projects in the ensuing years have made it clear that the couple never got back together. 

That ending was somewhat radical for 1990s cinema. Most films in or close to the romantic comedy genre have the man do something dumb, lose the woman, do something else to redeem himself, and get her back. Chasing Amy realizes that Holden was jealous, was unfair in his jealousy, and deserved to suffer for it. 

Some denounced the film upon its release as a “male fantasy” of getting a beautiful lesbian to sleep with him, but that critique only makes sense if you set aside the last 15 minutes of the movie. Also, Chasing Amy implied that the two men had more than friendly feelings for each other. Aside from specifically queer cinema, that was the sort of thing that, in the ’90s, tended to be implied in academic papers about film, more than in the films themselves. 

Sure, some aspects of the film’s sexual politics land with something of a thud to modern-day eyes. Banky’s blunt homophobia is pretty jarring, although it’s not like the film endorses those sentiments. 

The plot of Chasing Amy wouldn’t make much sense in the present day, because everyone understands now that some people are bisexual. For a female fictional character to date both men and women is far from a rare thing in today’s movies and TV today, not to mention in real life. 

Chasing Amy
Image: Miramax

These aren’t the sorts of issues that a straight male filmmaker could deal with, without blowback, in today’s environment, although Smith did date Adams in real life, and the jealousy angle was supposedly inspired by Smith pal Scott Mosier’s one-time crush on actress Guinevere Turner. And there’s also no getting around that the film, like all of Smith’s early work, was released through Miramax and funded by Harvey Weinstein.  

Chasing Amy made $12 million at the box office, exponentially more than what it cost, and earned mostly positive reviews from critics. It was a frequent dorm room watch at colleges in the closing years of the 1990s, as was Clerks. 

Ironically, the big leap in quality and maturity that Smith showed between Clerks and Chasing Amy did not continue, and he never made anything like Chasing Amy again. His next film, the Catholicism satire Dogma, is much more memorable for the controversy it kicked off than the film itself, and since the turn of the century Smith has gone back and forth between sequels to his older films — Clerks III is set for release later this year — and bizarre one-off projects like Yoga Hosers and Tusk, all of them geared toward’s Smith’s audience of die-hards and not many other people. 

At the same time, though, Smith’s podcasts, interviews, and live events are much more entertaining and watchable than his more recent movies. 

Smith, though, saw a few things coming, including the mass adoption of comic book culture — he gave Stan Lee a cameo in Mallrats, a decade before the MCU had that idea — as well as the movie star run of Ben Affleck. Speaking of which… 

Chasing Amy
Image: Miramax

I have a bit of a personal connection to this movie. In the spring of 1997, when I was a freshman in college and Chasing Amy was about to come out, I interviewed Ben Affleck, during his promotional tour for the film, at a hotel in Boston. 

In the interview, Affleck talked about a movie he was about to start filming called Good Will Hunting, and also fielded questions about whether his girlfriend at the time — his high school sweetheart, I believe — was jealous of him kissing other women on screen, just before he uttered the immortal line “I try not to date actresses, because they’re all insane.”  Within months he was with Gwyneth Paltrow and, of course, Affleck would spend the ensuing 25 years dating, and marrying, a succession of famous actresses. 

As Affleck’s career has had massive ups and downs over the next quarter-century, I’ve thought of that afternoon often. And I’ve thought often of Chasing Amy too, both a defining film of the late 1990s and a glimpse of what Kevin Smith’s career could have been. 

Watch Chasing Amy

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Written By

Stephen Silver is a journalist and film critic based in the Philadelphia area. He is the co-founder of the Philadelphia Film Critics Circle and a Rotten Tomatoes-listed critic since 2008, and his work has appeared in New York Press, Philly Voice, The Jewish Telegraphic Agency, Tablet, The Times of Israel, and RogerEbert.com. In 2009, he became the first American journalist to interview both a sitting FCC chairman and a sitting host of "Jeopardy" on the same day.

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