Chasing Amy and the toxic “nerd masculinity” of the nineties.

Kevin Smith’s romantic comedy Chasing Amy, now almost two decades old, was a big deal for my generation of nerds. Back in 1997, all of our dorky interests, from comic books to video games, remained hidden, far from the prying eyes of the American mainstream. To us, the unapologetic fanboy Smith had emerged as something of a nerd culture Shakespeare—the best of us, a man who captured our hopes and dreams in his character’s lengthy, pop culture–laced monologues. Chasing Amy, which concerned sensitive-yet-sleazy Ben Affleck’s pursuit of the bisexual comic-book artist Joey Lauren Adams, constituted Smith’s first serious attempt to tell a meaningful dramatic story against the backdrop of the geek demimonde he’d explored in his previous slacker comedies Clerks and Mallrats. We were supposed to identify with (or at least pity) Affleck’s comic-book penciler Holden McNeil as he tried to come to terms with Adams’ sexual history, which involved group sex and gay sex and all sorts of other activities alien to his own heteronormative experience.

Chasing Amy was always an uncomfortable movie, a film that encapsulated the worst aspects of narcissistic nerd entitlement at its late-nineties peak, but twenty years later I couldn’t even bring myself to finish rewatching it. When it was released, I begged my father to drive me to Raleigh’s Rialto Theatre and left that first showing enraptured, believing that some aspect of my privileged nerdy male “struggle” had been set to film. Kevin Smith was the first director whose scripts I had ever read; before I’d encountered his work, I hadn’t ever considered the form. It helped that Smith was such a dreadful cinematographer, a fact he admits without shame, because it meant his movies were the equivalent of ninety-minute script readings. Yet why, in the course of dreaming about becoming a “Hollywood writer”—whatever that meant—had I lingered over this material? How had it ever resonated with anyone at all, myself included?

The answer was simple but painful: I was one of those stereotypical “guys who liked movies,” and I was stupid.

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Throughout the nineties, TBS used the tagline “Movies for Guys Who Like Movies” to promote a schedule consisting of boneheaded action fare such as Universal Soldier and Red Heat. The testosterone-drenched “guy movie,” which exists as the obverse to the “chick flick,” has supposedly yielded a number of masterpieces. The late-seventies frat comedy Animal House, set in the simpler America of the pre-Vietnam sixties, is considered chief among the humorous “guy movies”; it transformed wild-man supporting-player John Belushi into a box-office star and milked prison rape and necrophilia gags for all they were worth. People like my brother remembered that movie as some kind of great milestone in cinematic history, a gross-out opus that launched a thousand subsequent tales of the old homosocial order: panty raids and hazing initiations generously surrounded by memorable quotes (“Thank you, sir! May I have another?”) that could be substituted for punch lines in awkward real-life social situations.

In my naïveté, I assumed that Kevin Smith’s work, which premiered in art-house theaters and looked like it was shot on a VHS recorder, was somehow more elevated than the campy Cannon Films “guy movie” dreck so beloved by my father and older brother. There was a self-awareness to it, a wink at the audience: “Hey man, you know about these neat things, so we’re in on this together!” Men have long fancied themselves spelunkers of the unknown, roaming the caves of the underground so that they can be the first to force potential romantic partners to sit through ten hours of The Wire or a bunch of Captain Beefheart LPs. Smith, like a lot of other almost-famous 1990s male artists and entertainers, piled on the references to win us over—and his attempts had the same hard-sell, look-at-me quality that Holden McNeil used to temporarily win Joey Lauren Adams’s affection. Wasn’t it all so smart, so important, so precious? And when Smith, playing his trench coat–clad “Silent Bob” character, opens his mouth to deliver the payoff “Chasing Amy” monologue to a disconsolate McNeil, we’re quite literally listening to the author demand that we acknowledge he’s an auteur.

As a piano tinkles in the background to underscore the gravity of what he’s saying, Silent Bob explains that he shouldn’t have reacted to the knowledge that his then-girlfriend had a threesome by calling her a “slut” and dumping her, but instead should have understood she “wasn’t that girl anymore” and was now “looking for the Bob.” This condescending realization is intended as an indication of broad-mindedness, letting sensitive, insecure men like Holden McNeil know that it’s okay to date girls who are more sexually experienced than they are. By the time Smith utters the titular line—“so I’ve spent every day since then chasing Amy, so to speak”—it’s obvious that his speech is male-oriented 1990s pop culture in microcosm. In the era just before the explosive growth of the Internet enabled individuals whose voices had long gone unheard to engage in a much wider conversation, we witnessed the last gasp of the “Big I,” the lone male mastermind who lured us back into his apartment and then demanded that we inspect his carefully curated collections of cultural ephemera, whereupon we would inform him what a thoughtful guy he is.

For many years, this was what I assumed masculinity, particularly nerd masculinity, was all about. Like Steve Buscemi’s seventy-eight-rpm record-collector Seymour in Ghost World, the true alpha nerd hunkered down in his rat hole of an apartment amidst a gilded gallery of material—references to drop, recommendations to make—and awaited the right moment to sweep some unwitting stranger off their feet. “I’ve never met anybody like you,” we all hoped our partners would tell us, even if that foreshadowed a bittersweet conclusion when we were informed that we were “too much.”

I ruined several romantic relationships in precisely this fashion. In each case, I wanted someone to tell me how brilliant and sensitive I was, how deserving of love I had made myself. I wasn’t like my emotionally distant grandfathers, one of whom could barely even speak English. Unlike those two shell-shocked veterans of the “Greatest Generation,” I had a million sweet nothings to say, and I only needed a best friend/romantic partner who would willingly listen to them all. I would save them from a life spent with some uncommunicative lummox, and they would rescue me from my parents’ basement. This is, of course, an unacceptable burden to place on someone else, and it invariably blew up in my face—though that was to be expected, maybe even desired, because it demonstrated that no one deserved the gift of my life. When it did, I turned to the melancholy music I thought provided the sound track to my so-called life.

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“We were good as married in my mind / But married in my mind’s no good,” laments Rivers Cuomo on the Weezer ballad “Pink Triangle,” which the eighteen-year-old model of myself once saw as profoundly affecting. Like Chasing Amy, the song explores a relationship, in this case a totally hypothetical one with an inaccessible woman, doomed by the unbridgeable chasm of sexual preference. Cuomo, who elsewhere in the tune hints at having also engaged in same-sex relations, whinges about how this particular manic pixie dream girl can’t bring herself to “be a little straight” for his sake. (Affleck’s Holden, interestingly enough, orders his best friend Banky to have sex with him as a way of saving their relationship, then French kisses him.) Such empty-gesture moaning was familiar territory for the Weezer frontman, who won a sizeable audience by pairing “Big I” pretensions with simplistic chord progressions and then packaging that work in memorable Spike Jonze and Marcos Siega music videos.

More to the point, Cuomo’s lachrymose lyrics offer insight into the psychological terrors at the heart of this kind of “Big I” work. Far from being the dashed-off musings of an insouciant mastermind, a song like “Pink Triangle” is actually an admission by the artist that he is terrified by the possibly that he doesn’t matter. The narrator confesses that this very meaningful-sounding relationship is a complete fiction, that his own heterosexuality (which he hopes his dream girl will embrace!) is itself suspect, and that his deepest desire isn’t so much dating her but planning his wedding, floral arrangements and all.

Fin de siècle nerd masculinity was so pushy and demanding—look at how awesome I am!—because, deep down, its practitioners were panicked and insecure. This kind of full-court press, all hipster Cyrano speeches and slick presentation, was analogous to bodybuilders hiding their inner weakness behind a wall of hypertrophied muscle: ditch the packaging, they worry, and their admirers will ditch them. The self floats on the surface; nothing lies beneath.

Some of this material is better than the rest, albeit no less problematic. David Foster Wallace’s writing, for example, is overstuffed and show-offy, but the narrator is so distant and so brilliant that he doesn’t appear to want our affirmation (even if he so desperately does, because he recognizes, as in his lauded short story “Good Old Neon,” how empty the life of a lonely genius is). Quentin Tarantino’s movies about movies are open to charges of misogyny and racial insensitivity, but they appear to exist in a parallel universe that has nothing in common with this one except spaghetti westerns and blaxploitation flicks. Even so, it seemed there was no end to this generation of singularly deep young men, each of whom appeared hell-bent on forcing us to operate with blown minds and broken hearts. Some were more accomplished than others, but each positioned himself as a sensitive artist desperate to be told how clever he was.

But the passing of time is neutral, and pieces praising generations of rising stars eventually yield to postmortems recapping what the heck actually happened. Such is the epilogue to Chasing Amy: after Ben Affleck and Joey Lauren Adams have their final meet-not-so-cute, Adams’s new girlfriend asks her who Affleck is. “Oh, just some guy I knew,” she replies. The same could be said of who I was—who many of us were—during this turbulent transitional period just before crowd-pleasing filmmakers such as Christopher Nolan and J. J. Abrams fused nerd and mass culture into one all-encompassing monoculture, forcing privileged nerds to concede their private spaces to a larger and more diverse public now interested in that formerly “underground” material. Kevin Smith is still around, making small and forgettable horror movies on the Hollywood periphery, but his moment in the semi-spotlight has passed.

He did get pretty close to the big time, though. Once the stuff of fanboy dreams, Smith’s unproduced Superman Lives script continues to float around the Internet. It was commissioned by Warner Brothers in 1997, at the height of the writer/director’s fame, and now seems small and quaint by the standards of today’s bloated by-the-numbers Marvel Studios blockbusters. One scene, however, warrants mention: after dealing with the threat posed to Earth by a rebuilt Brainiac, Superman turns to Lois Lane and quips, “From now on, I’m going to be more man than Super.”

That’s keen if slightly vague advice for all of these nerdy masterminds, so eager to impress by behaving like someone they aren’t in order to prevent others from learning who they actually are. Such masculine panic and posturing ultimately comes to naught, because it turns out nobody else is searching for that underlying reality and we’re only deceiving ourselves. Acknowledging this truth by replacing the entitled attitude of the know-it-all indie nerd with candor and genuine vulnerability is a tall order, but it seems like a necessary step for improving relationships with friends and romantic partners.

Oliver Bateman is a historian and journalist who lives in Pittsburgh.