It would be an exaggeration to say watching High Fidelity persuaded me to move to Chicago nearly two decades ago, but it didn’t hurt. Stephen Frears’s film adaptation of Nick Hornby’s 1995 novel showed me a world I fervently wanted to live in, a place of funky shops, laid-back concert venues, and a culture scene inextricably tied to alt weeklies. It’s not that I wanted to be Rob Gordon, John Cusack’s lovable-loser antihero, but I longed to enter his orbit. Championship Vinyl, his fictional workplace, was my dream version of a record store: deeply stocked, disorganized, and staffed by clerks who, if they decided they liked you, would point you in the direction of the best music you’d never heard. This was not the Chicago of Ferris Bueller’s Day Off or The Fugitive, two movies that had shaped my early imaginings of the place. This was something better.

By the start of the 2000s, I’d made enough visits to the city to know that, no, you couldn’t buy LPs at the corner of Milwaukee and Honore, which is where Championship Vinyl was ostensibly located, but you could, as Rob points out, see a movie where John Dillinger was shot and then cross the street to catch a band at the Lounge Ax, where Rob befriends the alluring singer-songwriter Marie De Salle, played by Lisa Bonet. You could also see live music at the Double Door, where Jack Black’s character sings “Let’s Get It On” in the movie’s climactic scene. And to judge by my friends who already lived in the city, you could definitely rent the sort of impractically designed, meaningfully cluttered apartment that Rob inhabited. That turn-of-the-millennium Chicago — with its Beta Band soundtrack, Pavement posters, and smoky clubs — was there for me if I wanted it. After High Fidelity came out, I wanted it bad.

I got my chance in 2001, when my employer, The Onion — a visual reference to which, incidentally, can be seen in a few frames of the film if you look closely enough — moved me from Madison, Wisconsin, to Chicago. My girlfriend and I ended up in Andersonville. A historically Swedish neighborhood, it was then still dominated by laundromats, odd restaurants like the diner that served both hamburgers and Chinese food, and funky holdovers from previous decades: a sprawling secondhand shop with a basement dedicated to old marching band uniforms, an auto garage whose employees sometimes watched porn movies in full view of passersby. (I miss some of the neighborhood’s vanished denizens more than others.)

Venturing farther afield, I visited bookstores like the Gallery on Belmont, a still-standing bastion against gentrification that forbade cellphone use and in which stacks of books hid still more stacks of books that seemed to extend infinitely into the building’s dark recesses. That the owner seemed to wait for customers to share a secret password before offering help made the place feel like the literary kin to Championship Vinyl. I watched arthouse films that would take months to reach Madison, if they got there at all. At the Music Box, where Rob and one of his exes take in The Dreamlife of Angels, I saw a version of Orson Welles’s Touch of Evil that had been painstakingly restored using Welles’s own notes. In Wicker Park’s Flatiron Arts Building, a sort of cross between an art colony and a flea market, I found a shop selling bootlegs of sci-fi and horror movies I’d only read about in books.

John Cusack as Rob Gordon
John Cusack as Rob Gordon, taking stock of his records and his life Photo: Getty Images

Chronicling it all were papers filled with listings and ads for what was happening that week: a screening of Iranian director Hassan Yektapanah’s Djomeh at Facets, a concert by the up-and-coming Chicago power-pop band Frisbie, a reading by Jeanette Winterson at Women & Children First. In those same pages, I devoured commentary from writers I’d admired for years: Roger Ebert, Michael Wilmington, Greg Kot, Jim DeRogatis, Jonathan Rosenbaum (whose film scholarship was instrumental in that Welles restoration).

I soon found out, though, that you never get to fully enjoy the city you aspire to live in. By the time you arrive, it’s already started to change. My girlfriend and I did manage to see films at the dilapidated Biograph — including a memorable screening of Bad Santa during which a few patrons smoked freely in their seats — and shows at the Double Door. But we never had a chance to go to the Lounge Ax. It had closed by the time the film came out in March 2000. The Double Door would hang on longer, but in 2017 an eviction notice was slapped across its entrance.

From The Onion’s office — which occupied a building on Belmont that’s been replaced by a Target — I tracked a rapidly changing cityscape, as record stores closed and weird shops and corner stores gave way to chain restaurants. I saw the friendly, family-owned newsstand at the Belmont L stop, part of Rob’s route between home and work, disappear and vending machines take its place. By the time I left The Onion in 2012, the publication had long since shifted its focus to the internet, but it still felt like a blow when, a year later, the print edition ended its run. The Chicago Reader and Newcity live on, but the prospect that someone like an ex-girlfriend of Rob’s would have a full-time job reviewing movies for an alt weekly like those now seems somewhat preposterous.

Still, I take heart in the fact that some of the film’s landmarks remain with us. The Music Box continues to thrive. The Green Mill will likely still be hosting late-night sets and sending patrons into the night looking for after-hours tacos long after everyone reading this is gone.

It’s easy to grow disenchanted with the ways time has swept the Chicago of High Fidelity away, but those of us who lived through that era should remember that we’ve changed too. I used to know every band that played the Metro when busing past it was part of my everyday commute. Now I mostly know the older acts. I used to stay out late. Now I rarely see the city after dark. I married the girlfriend I moved here with all those years ago, and we’re parents now. I get tired more easily than my 28-year-old self. I mostly stick around the little piece of the city I call home.

It all makes me wonder where Rob would be now. Would he have settled down with Laura to enjoy the profits from the label they launched? Or maybe he’d still be single, hosting sad ’80s nights in suburban clubs. I guess it doesn’t matter. There are others waiting to make Chicago their own and rework it in their image. They might not have a movie that preserves the moment forever, but they’ll find other ways to remember their city. And someday, years from now, they’ll wonder where it went.