In the 1970s, Chicago’s Uptown neighborhood was a hotbed for people looking for something better—and their music

By Jonathan Dale

Chicago should have been a country music town. It first occurred to me in the summer– I was depressed and working as a barista, so what else was there to do but wander around my corner of the city? From my neighborhood, Edgewater, I’d meander east to the lake, north to Devon, or south through Uptown, and the music of Jeff Cowell became my soundtrack. Cowell is a singer-songwriter from the Upper Peninsula of Michigan, the remote piece of land stretching like a curved finger from the top-right corner of Wisconsin, resting on top of Michigan’s mainland mitten. After graduating from high school in 1969, Cowell drifted around the country, playing his folk songs where he could for a bed, meal, or beer. Among other sojourns, he had a failed pilgrimage to San Francisco (the truck he jumped aboard broke down in the desert of Elko, Nevada), and eventually circled back to the Midwest. In 1975, he recorded his defining album, Lucky Strikes and Liquid Gold. The record, a group of country-tinged folk and rock songs, is a pocket of broken-down Americana charged by Cowell’s endearing hippie optimism. To my surprise, I learned he had recorded the album in Chicago, just blocks from my apartment– maybe he walked the same sidewalks I did.

Lucky Strikes went unheard for forty years–Jeff had long given up on music, viewing his brief career as a failure– until it was reissued in 2015 by the Chicago label Numero Group. Cowell’s album is a new addition to Chicago’s scattered country music history: a down-and-out folk album pulled from windy Michigan highways and the melding country-rock of Chicago’s honky-tonks. As a genre, country music’s cultural footprint is significantly more limited in Chicago than forms like gospel, blues, and house. But Cowell’s album points to a lineage of Midwestern folk-country music, a chronology of outsiders drawn from across the Rust Belt to Chicago.

Country music’s winding history in the city has existed on the fringes, not so much a canon as a staggered line, low-humming but consistent. While the city had its national moment in the late 1990s with Alt-Country, Cowell put his own pin on the style decades before Uncle Tupelo pulled in from Belleville. John Prine, a son of Kentucky and patron saint of Chicago folk music, put the city’s roots scene on the map in the early 1970s. Later, Chicago-based Bloodshot Records titled their flavor of country-punk “insurgent country.” Musicians like Jeff Tweedy, Neko Case, and Jason Molina would make Chicago their own.

But in tracing country music’s winding path through Chicago, maybe the most interesting moment is the mid-70s, at what (now, in hindsight) seems to be an inflection point for Chicago’s postwar Appalachian population and the musical traditions they brought. Southern musical culture had intertwined with Uptown’s gritty image, and as Jeff Cowell worked on his album, Appalachian migrants, part of the neighborhood’s diverse coalition, fought for a place in the city.


Chicago was primed for (and briefly held) a major role in country music. In 1924, Sears-Roebuck created its own radio station, WLS, to better advertise itself to rural white communities. Chicago’s central location gave it a far-reaching broadcast radius. One of WLS’ first shows, National Barn Dance, would become the most popular country music program in the country, creating early stars like Gene Autry. The first music variety show of its kind, Barn Dance was a pivotal moment for how “country” music became codified. The American form that originated with Black southerners and the blues morphed into country with the inclusion of the banjo (a traditional African instrument) and the fiddle from Europe. Barn Dance pulled the broad catalog of roots music, hillbilly, folk, and traditional ballads together in a cohesive and far-reaching medium, with a sepia-toned nostalgia for the country’s southern white farmer. But National Barn Dance’s popularity (and star-making opportunity) was soon supplanted by Nashville’s Grand Ole Opry.

As the National Barn Dance pulled ears around the country, Chicago’s Uptown neighborhood reached its most opulent. A booming entertainment district had formed, bolstered by the Pre-Hollywood film industry, multiple grand theaters, and a steady stream of vacationers flocking to nearby Lake Michigan. But after World War II, the neighborhood sagged under white flight. Uptown became a port of entry for successive waves of poor migrants. By 1974, the Chicago Tribune described Uptown as having “a prevailing style that can best be described as 20th Century Bleak.”

Uptown became a major stop on the “Hillbilly Highway”, the out-migration of Appalachians leaving the shrinking coal industry for a better future in the industrial north. With larger families and kinship networks, many chain-migrated, joining an older sibling or a cousin who was already in Uptown. Those who migrated found a place that was exciting but culturally jarring. Appalachians were seen by Chicagoans as pariahs and treated with hostility and anti-hillbilly prejudice. However, their impact on the city shouldn’t be understated– as many as seventy thousand joined the transitional Uptown community from the mid-South from the 1950s on.

Appalachians joined Uptown’s contingent of Native American, Puerto Rican and African-Americans standing up for their rights. As the Civil Rights Movement grew across the country, Uptown became a fertile ground for struggle, where poverty, dangerous living conditions, and police brutality made life tenuous and inhospitable. As Mari Cohen has written previously for this magazine, a multiracial coalition fought with the city over “what Uptown’s future should look like, and whom it should be designed for—questions that remain at the heart of political battles in Uptown and across the city today.”

Urban Native Americans, pushed from their reservations by the Indian Removal Act of 1956, founded The American Indian Center, the first such community center, in Uptown in 1953. In 1970, Carrol Warrington, a Menominee woman, and other Native Americans set up a Teepee outside of Wrigley Field to protest squalid housing. Chicago’s late 1960s wave of interracial solidarity also touched Uptown. Uptown’s Young Patriots, formed from white Appalachians, worked in concert with the Black Panthers and the Puerto Rican Young Lords to form the Rainbow Coalition. By 1975, Jose “Cha-Cha” Jimenez, Rainbow Coalition co-founder and leader of the Young Lords, mounted a grassroots campaign to be Uptown’s Alderman.


Urban Appalachians were down and out in Chicago, and it’s reflected in the music. Maybe the most striking song, “Sidewalks of Chicago,” made famous by Merle Haggard, is narrated by a destitute migrant who is thankful no one from his home in Kentucky can see how low he truly is. Haggard performed the song in 1970 on the Johnny Cash Show. The song is a tired plea, far from home.

Southern white migrants opened honky-tonks, giving the city venues to dance, drink, and listen to country music until the morning. “Throughout the 1950s and 1960s,” wrote the Tribune in 1978, “Uptown seemed to shrink beneath its layer of grime, covering its shame with a splash of neon and a dirge of country music.” Honky-tonks were consecrated in Blues Brothers’ encyclopedic vision of Chicago’s post-war musical traditions; the bar’s drunken crowd throws bottles (angrily) at the out-of-place band, but then transitions to throwing bottles (celebratorily) when the band changes to a popular western tune.

John Prine was from the working-class Western suburb of Maywood, where his family settled after leaving Kentucky in 1923. As Erin Osman writes in her book on Prine’s self-titled debut, “Prine’s father Bill loved traditional country, western swing, and jazz…Bill also brought the boys to his favorite watering holes, no-frills dive bars with plenty of country music on the jukebox.” In 1970, John Prine was discovered by Roger Ebert at an open mic, and his unpretentious, funny, and often devastating story-songs joined the new American songbook.

In a testament to the southern white impact on Chicago, a proposed low-income urban village was named for country music star Hank Williams. The city wanted to build a new junior college, and chose a section of Uptown as the site for the project–  Hank Williams Village was a counterproposal. “The fight for Hank Williams Village can be viewed as a turning point for Appalachians, who were characterized as transient, unstable, and and not expected to remain in the Windy City,” writes Roger Guy in his piece “Hank Williams Lives in Uptown.” It was a chance to plant a sturdy Appalachian flag in the ground, “a statement of the importance of Uptown for Appalachians.” But Uptown’s pro-business contingent was not looking to cede sovereignty, and Hank Williams Village never made it to construction.

The development process was contentious. Chuck Geary, an Uptown Appalachian organizer who helped envision Hank Williams Village, “began each protest by breaking out his guitar and singing a song called ‘Hillbilly Heaven’.” Leading a protest against the college, Geary stood at the podium and said, “we are not going to trade one gutter for another.” Truman College’s construction destroyed twelve hundred affordable housing units, and “in the course of its construction, the nucleus of the southern white population in Uptown was displaced,” writes Guy.

While stereotyped as lazy, Appalachian migrants were trying to make it work in Chicago. Hank Williams Village was a dashed opportunity for a deeper sense of ownership over Uptown. And honky tonks were not immune to this struggle to grow deeper roots, either. By 1974, a Tribune article titled “Chicago’s Curious Country Music Explosion” wondered why country music venues weren’t sustaining success. “I really think the situation has deteriorated,” said Joel Daly, a local newscaster and newly–evangelized country music fan, in the 1974 piece. “It’s now at the point where not very many good country musicians seem to survive here.” While country music was popular on the radio, opportunities for live performance, necessary for young musicians, were being cut out as honky-tonks closed or moved to the suburbs.


One reason Jeff Cowell’s music is noteworthy is that he grew up in a mining town, but not in West Virginia or Kentucky. When American settlers discovered iron in the Upper Peninsula in the 1840s, the region boomed with industry. The ore mined in the UP was shipped down the Great Lakes, smelted in the factories, and turned into the mythologized steel that built Chicago.

The Upper Peninsula is almost completely surrounded by Great Lakes, densely forested, and sparsely populated. It’s wilderness, and one without much of a popular cultural footprint. But you can feel the Upper Peninsula in Cowell’s music: the wind, the roadside bars, the weary huffing of a beater on its last mile.

Cowell recorded his music at the home studio of Word Jazz visionary Ken Nordine in Edgewater. The Lucky Strikes and Liquid Gold sessions were helmed by Ken’s son, Kris, who took Cowell’s folk sound and gave it a full band jolt. Regarding Lucky Strikes time and context, Cowell said “Country was kinda happening, the cosmic, New Riders of the Purple Sage, Grateful Dead, then The Eagles slid in. There was that feeling in the air. It was leaning to that hippie country, it wasn’t Nashville country, it was a different trip.”

On the title track, over piano and pedal steel, Cowell has a reckoning with the costs of addiction. He needs to drink, needs it more than the woman begging him not to go back to the bar. He pleads with her to understand that it’s nothing personal. Then he walks out. His confession of helplessness is jarring, brutal honesty. A lesser singer would come across as callous or cruel, but Cowell’s voice is weary, almost gentle, like he’s tired of himself but can’t muster the power to change. It’s an exceptional and singular song.

Cowell didn’t spend too much time in Uptown, but his transient early adulthood gave him a vantage from the fringe. “I was in and out of work,” Cowell said. “I was bumming it, hitchhiking, and oftentimes it was downright depressing, and lonely, and [I was] very unsure of what the next day was going to bring.” Lucky Strikes’ first track, “Jake Lake”, tells the story of an isolated alcoholic. Cowell remembers the homeless people he saw in Uptown, saying “…I wasn’t that far away from that guy…the unfortunate guy sitting on the sidewalk. I was kinda homeless in the same boat at certain points.”


Today, musical evidence of a honky tonk past is scant. Bloodshot Records released a compilation of longtime Chicago act The Sundowners, who held down a decades-long live gig at then-infamous downtown Bar Double R Ranch. Included in the release is a cover of “Sidewalks of Chicago.” Another Bloodshot Records compilation, 2019’s “Too Late to Pray: Defiant Chicago Roots” leads off with “The Last Honky Tonk in Chicago”, a song wondering about the now empty scene while comparing the success of other genres to country’s shrinking presence.

Without a growing honky-tonk presence, the ability to cultivate a vital musical scene specifically geared toward country was marginalized. Besides Prine and Tweedy, naming notable country-influenced Chicagoans is a task. Instead, Chicago’s country lineage is mostly populated by loners and stragglers, who embrace a musical palette that is much wider than traditional country.

But there is still one bar from the honky-tonk days: Carol’s Pub, in the heart of Uptown. Carol’s opened in 1972, and stayed in business until 2016, when the bar had its liquor license revoked due to unpaid taxes. In 2018 it reopened under new ownership– remodeled but still a place for country music. In a New City profile from 2012, when she was still proprietor, owner Carol Harris was optimistic: “When the neighborhood began to change fifteen years ago we thought we would see a drop in business,” Harris says, “but we found out that yuppies like country too.”

Chicago never did become a bastion of traditional country music. If you wanted that, you’d just find your way to Nashville. But the music that it did produce is decidedly not traditional. Musicians interested in country music zigged when the country music establishment zagged. What emerged, owing to its surroundings, was a blending of country elements with folk, rock, and punk music. Venues like the now-gone Lounge Ax–which shows up in the Chicago film High Fidelity–were able to elevate Chicago’s ‘90s indie scene with a variety of independent musical acts. And Chicago’s punk ethos, which drives far beyond just country music, is able to include it.

The title of this piece is the refrain in Tom Waits’ “Chicago”, a song of anxious propulsion from the perspective of a migrant, voicing the wishes and fears of the city’s newcomers. People were (and still are) moving to Chicago, Uptown in particular, for their next step, for an opportunity they couldn’t find elsewhere. Some might “make it” and stay, others won’t, and they’ll keep searching. But they all become part the city’s story. “I enjoy Chicago. If you have money and time it’s a wonderful city, it’s got everything. [But’] I’m a small town dude, I didn’t want to get caught in that,” said Cowell.

On “Not Down This Low”, the final song of Lucky Strikes, Jeff Cowell echoes a similar sentiment to “Sidewalks of Chicago”– down bad, the only consolation that at least nobody you know can see you. “I got a family I had to leave way up north”, Cowell sings. “I hope they think that I’m dead, but not down this low.” After his music was re-released, Cowell found his redemption. Uptown has always been a jumble of people and pathways, shuffling new traditions with old and creating something uniquely Chicago– and all of it happening on those same sidewalks. ■



Jonathan Dale is a freelance writer from Chicago with work in South Side Weekly and the Chicago Reader. You can find him on Twitter @dalejondale.

Cover image: Uptown, Chicago in 1974. Photo by Danny Lyon/EPA.

Belt Magazine is a 501(c)(3) nonprofit organization. To support more independent writing and journalism made by and for the Rust Belt and greater Midwest, make a donation to Belt Magazine, or become a member starting at just $5 a month