As a suburban, white, Jewish male growing up in New Jersey in the 90s, it never occurred to me that most of the pop culture I loved was not for me.

That might sound like an absurd notion given the “white” and “male” parts, but when I think back on the entertainment that I thought defined me, so much of it was created outside of the world I lived in.

Perusing my CD binder, you’d have found an assortment of hip-hop albums from Nice & Smooth, A Tribe Called Quest, and Snoop Dogg. Clearly, they weren’t rapping about any kind of life I was familiar with. You might also have found rock albums from Rage Against The Machine, Nirvana, and Tool, none of whom were singing about anything I could relate to on a day-to-day level (in Tool’s case, that’s probably a good thing). Hell, even the Beastie Boys, white boyz though they were, spoke with a swagger and city-lived confidence I couldn’t ever connect with on a soul level. When it came to comedy, Chris Rock’s Roll with the New was basically on repeat for a year, but there are whole swaths of that set that I could never say out loud, let alone associate with. I enjoyed all of this pop culture, but I don’t think I ever really understood any of it.

I think that’s what made the world of Kevin Smith’s early movies so exciting. When Clerks came out in 1994, I was a dorky high school junior in Central New Jersey not far from The Shore. If I wanted to, I could have driven (with a licensed adult in the passenger seat until the next year) to the Quick Stop and RST Video stores featured in the film and seen them for myself. The conversations Dante and Randal had about Star Wars, sports, and girls were the kind of conversations I might’ve had, or wanted to have if my friends and I had been quippier. Plus, all of the actors in the film were real. Actual people from New Jersey. So real, in fact, that I would one day meet the actress who played Caitlin Bree at my friend’s wedding, of which she was the planner.

For once, I could reach out and grab a piece of pop culture and it felt tangible. It felt like watching a part of me and my life, albeit without the bathroom corpse sex.

Mallrats came out in 1995 and while the production values were slicker and the acting (slightly) better, it still spoke to me as a story told by a Jersey kid to this Jersey kid. There’s an establishing shot in the film when Brodie and T.S. go to the flea market and I recognized it immediately. It was a mall on Route 1 I used to go to before it got torn down. And again, the references hit home. Brodie playing a hockey video game and trying to beat the high-powered Canucks with the “The Whale” was the kind of thing I spent too many weekend mornings trying to do. Even just the idea of the movie itself spoke to me. Aimlessly hanging out in a Jersey mall made up roughly 67 percent of my childhood.

At this point, I went off to college. I didn’t travel too far, just Upstate New York, but it still felt like a million miles away to a suburban Jersey kid who didn’t know anything else. It was my first taste of life outside of what I’d known and lord knows I didn’t quite know what I was getting myself into. Least of all when it came to understanding women, or understanding myself around women.

All of which brings us to Chasing Amy, Kevin Smith’s third feature film, which debuted in theaters 20 years ago (April 4). It’s often referred to as Smith’s first “grown-up” film, though that label is debatable given the breadth of sexual and scatalogical jokes woven throughout. Watching it for the first time, however, I did remember noting a sense of urgency behind it. I didn’t quite know this at the time, but Mallrats had been a critical and commercial failure and Smith’s career was already moving backwards. The million-dollar budgets and wunderkind label were gone and he was going to have to prove with Chasing Amy that he really was a filmmaker and storyteller worth investing in.

As far as 19-year-old me was concerned, he did that and more. I loved Chasing Amy. I loved that it had all the Kevin Smith trademarks coupled with this newfound sense of honest discovery. Attempting to dig into the world of bisexuality still felt edgy (to me) and modern. Banky’s four-way road riddle became a go-to monologue for so many male actors over the next decade. And the ending, a depressing gut-punch that stuck with me because Holden’s decisions seemed moronic and yet brutally realistic.

My love affair with Kevin Smith’s films continued with Dogma, which had some great ideas that never quite coalesced into a cohesive story, and Jay & Silent Bob Strikes Back, which I will always appreciate if only for the Good Will Hunting 2 scene. All the while, I remained an unrepentant fan of Kevin Smith and his film catalog, which always retained something of those suburban Jersey roots that we shared.


It wasn’t until 2004 when I was 26 and saw Jersey Girl opening weekend in the theaters when it started to occur to me that while I was starting to grow up, perhaps Kevin Smith wasn’t. Or at least, perhaps his films weren’t. That notion really hit home when Clerks II came out in 2006. By all accounts, I should have loved Clerks II. On paper, this was everything I should want. And yet, 28-year-old me walked out of the theater feeling sad. It wasn’t relevant. It didn’t have anything new to say. It just felt like Smith was going back to a safe place because he didn’t like the way critics were treating him. In fact, you could argue his entire career since then has been a reaction to that.

With Clerks II, I finally felt like I had grown out of Smith’s movies. With each successive film, I grew more and more disinterested in what he had to say as a filmmaker and storyteller.

The problem with feeling like that is that when I look back on the early Kevin Smith films that I loved and thought defined me, the one that gives me the most pause is Chasing Amy. What felt edgy and modern at the time now feels like it misunderstood its subject entirely. Others have encapsulated the ideas surrounding the story better than I, discussing its narcissistic nerd entitlement, steeped in important male paranoia at the expense of female sexual empowerment. That doesn’t even get into the whole lesbian-turned-straight thanks to some “deep-dicking,” which is a joke made in the film but also kinda what happens as well. And in the end, we’re left to really only feel bad for the man in this story, the “true victim.”

The aforementioned four-way riddle is itself a red flag that demarcates a place and point of view that the film probably didn’t quite intend. Banky presents Holden with four people: Santa Claus, The Easter Bunny, the easy-to-get-along with lesbian, and a bitter dyke. Banky’s solution is that only the bitter dyke is real because the rest are figments of Holden’s imagination. Lost in that is the notion that, removing Santa and the Easter Bunny, you’re left with only two types of lesbians in the world. While that’s certainly reductive and meant to paint Banky a certain way, the film never quite goes out of its way to disprove that notion either.

While an earnest attempt to work through his own masculinity issues (as well as dip his toe into topics such as homosexuality and race), Smith never quite gets there because he’s too caught up in how all of this affects Holden. I suppose you could say Holden’s self-serving decision-making in the climactic scene, which doesn’t take into account the feelings or emotions of either Banky or Alyssa, serves as a perfect example of how so many men can’t get out of the way of their own ego when sex is involved. But the film, consciously or unconsciously, also leave us with the notion that his was the only point of view that really mattered.

I don’t hate the film, mind you. It still hits a lot of nostalgia buttons for me and probably always will. Watching it in my late 30s, however, is an extremely different experience to how I watched Chasing Amy as a 19-year-old. There’s so much I don’t think I understood about myself back then and maybe that’s why it felt so relatable at the time. As badly as Holden handles things in the film, I’d probably have done it just as badly, if not worse. Even now, those topics can be a tricky minefield to walk, not just with the other person but with yourself. But I’m not that kid anymore and we don’t live in the world that Chasing Amy was made in anymore. We’ve grown up (well, some of us) and moved on.

It’s been a long time since I lived in New Jersey, same goes for Kevin Smith. I’ve seen a lot more of the country and the world since then and I’m glad for all the experiences, good and bad. Like so many pieces of pop culture I clung to at some point in my life, Chasing Amy will always have a place with me. But whatever I thought I learned from it as a young man, I’ve decided to leave back there.

About Sean Keeley

A graduate of Syracuse University, Sean Keeley is the creator of the Syracuse blog Troy Nunes Is An Absolute Magician and author of 'How To Grow An Orange: The Right Way to Brainwash Your Child Into Rooting for Syracuse.' He has also written non-Syracuse related things for SB Nation, Curbed,, and many other outlets. He currently lives in Chicago.