At the turn of the century, John Cusack came home to Chicago to shoot a movie called High Fidelity. In it, he played a sad-sack hipster hiding out from adulthood in his used record shop, Championship Vinyl. Toward the end of the film, a young woman walks into the store and introduces herself as Caroline Fortis, a music reviewer for the Chicago Reader, the city’s alternative weekly. “You’re Caroline Fortis?” Cusack says, incredulously. “I read your column. It’s great. You really know what you’re talking about.” He’s so smitten, he makes her a mix tape.

Vinyl records. Mix tapes. Alternative weeklies. They seem part of another era now. But in 2000, when High Fidelity came out, the Reader was still a totem of Chicago’s underground scene. Every Thursday, stacks of fat, four-section papers were piled in the lobbies of bookstores, coffee shops, nightclubs, and liquor stores. By that evening, the Reader was under the arm of every L rider on the way home from an office job in the Loop, and in the backpack of every thrift-store chick on a one-speed bike.

The paper was the source for music listings and apartment classifieds. Starting on the cover, and winding through the ads, was a long, reported-to-the-pencil-nub tale about curing multiple sclerosis with bee venom or corruption in the Tollway Authority.

Today, if you made a movie about Chicago hipsters, Caroline Fortis probably wouldn’t write for the Reader. She’d write for Time Out Chicago, or Pitchfork, the music Webzine. The Reader still hits the streets every week, but as a single-section tabloid. Last year, shortly after its purchase by Creative Loafing, the Tampa-based chain, the paper laid off its entire design staff and four investigative reporters. And there’s a feeling around Chicago that the Reader has failed to catch on with the younger generation, and perhaps failed to try, at least until recently.

In 1995, when I quit my job at a downstate Illinois newspaper and moved to Chicago, my goal was to work for the Reader. I broke in with a long narrative about learning to play the horses from a professional tout, and worked my way up to staff writer. It was the best job I’ll ever have. At the Reader, you could write about anything, at any length, in any style. I turned out pieces on a teenaged Frank Sinatra impersonator, a man who sold socks by the freeway, and the “callers” who drummed up business outside hip-hop boutiques on the South Side. When I wrote my first book, Horseplayers: Life at the Track, the Reader paid my salary while I went to the races every day. All I had to do was write about the gamblers, a subculture the Reader loved.

The Reader was launched in 1971. At the time, the paper’s lakefront stronghold was populated by a mix of gays, artists, musicians, actors, and young professionals who were skeptical of the first Mayor Daley’s political machine. The so-called Lakefront Independents were key swing voters during Harold Washington’s 1983 campaign to become Chicago’s first black mayor. Right before the election, the Reader published an article aimed at reassuring white voters about Washington’s credentials. Widely copied and stuffed under apartment doors, it helped him squeak to victory. Throughout the council wars between white aldermen and Washington’s minority allies, the Reader remained in the mayor’s corner. Its star reporter, Gary Rivlin, went on to write Fire on the Prairie, the definitive book on that divisive era in Chicago.

As a newspaper that serves a narrow circulation area, the Reader doesn’t get to choose its audience. And the yuppies who’ve colonized the lakefront over the last twenty years don’t seem as interested in rage-against-the-machine muckraking. Lincoln Park, the heart of Reader Country, now has one of the few Republican ward offices in the city. The average home sells for $525,000. The new residents love the current Mayor Daley, who is considered less corrupt and racist than his father. They credit him with making the city safe for Barneys New York and Japanese restaurants with valet parking. The Reader still carries the banner of the Lakefront Independents, but that movement is down to one or two aldermen.

Edward McClelland is the author of The Third Coast: Sailors, Strippers, Fishermen, Folksingers, Long-Haired Ojibway Painters and God-Save-the-Queen Monarchists of the Great Lakes.