That migration didn’t completely hollow out Chicago’s country and folk scene, but rather made it a city of auteurs “who could freely experiment, perform, and collaborate because they existed far from the star-making structures of Hollywood, Broadway, and Nashville’s Music Row,” Guarino writes.

In some ways, it’s flourishing again in the alt-country community, which has been a vital part of Chicago’s music scene since the 1990s.

The more Guarino researched all of these eras in Chicago’s history of country and folk, the more connections he found between them. “Every generation did something completely of its own,” he said. “But what they were doing was very much tied into this tradition.”

A decade of digging

Growing up in Oak Park, Guarino, 53, heard his parents playing folk records, but he didn’t know much about country music. He learned to love alt-country and roots music in the 1990s — when he was in his 20s — as he spent many nights at FitzGerald’s, the Berwyn concert venue.

“A lot of my friends were going off to get graduate degrees, but I felt FitzGerald’s was my graduate school,” he recalled. “I really discovered that there was all this music out there that was not played on the radio whatsoever. It was just music from the small towns in America.”

When the Daily Herald in Arlington Heights hired Guarino as a music critic in 1997, he used that job to document Chicago’s burgeoning alt-country scene, which was anchored by Bloodshot Records and venues like the Hideout, and a big cast of talented musicians, ranging from Wilco, Neko Case and Robbie Fulks to two immigrants from Britain’s punk world: Jon Langford and Sally Timms of the Mekons.

“It was this ecosystem of incredible music that was all linked together, that was all vibrantly alive in the city at the time,” Guarino said.

Guarino spent a decade researching Country and Midwestern, digging through archives and old newspaper stories. He anchors his archival findings with interviews with many key players, including Bonnie Koloc, Charlie Musselwhite, Dale Watson, Tom Paxton, John Hiatt, Ed Holstein, and the late John Prine and David Crosby.

Guarino traces the history back to April 19, 1924, when the Barn Dance began broadcasting on WLS. For the next two decades, the show featured stars such as Gene Autry, making Chicago “the nation’s commercial heart of country music,” according to Guarino.

“It was the first show that became mass entertainment,” he said. “They were presenting it in a way that was designed to be familiar, to be really entertaining, to be very sweet, to be very wholesome. And to develop loyalty, so you’d want to tune back again.”

The real-life musicians on the show became something more like characters. “They were just regular people, not even intending to go into show biz,” Guarino said. “They were as unvarnished as you could get, but they became somebody else.”

Rural musicians came to Chicagoland in search of jobs – and not necessarily musical jobs. Kentucky native Bill Monroe, the “Father of Bluegrass,” moved to East Chicago, Indiana, in 1929 and worked for several years at the Sinclair Oil refinery, unloading empty 56 gallon oil drums from freight trains and cleaning them with gasoline. Monroe later returned to Chicago in the 1940s, recording his most famous song, “Blue Moon of Kentucky” at Columbia Records’ studio on the Wrigley Building’s second floor.

By the 1950s, country music was often heard at bars along West Madison Street, which were notoriously rowdy. Where the United Center is today, “that’s where the vice district was, a lot of prostitution and gambling,” Guarino said. “And of course, in the middle of it was country music. That was really the only type of music that was being played there.”

As Mayor Richard J. Daley pushed urban renewal projects, clearing out Skid Row, the honky-tonk scene shifted to the North Side. In a 2016 interview, singer-songwriter John Prine told Guarino about visiting honky-tonks near Wrigley Field. Prine, who died in 2020, recalled his father’s advice about drinking alone at these places: “You walk in and you find yourself a place at the end of the bar. And you order two beers – one to drink and the other to hit the guy over the head with if he attacks you.”

Uptown’s Appalachian community was a hotbed of country music. “There was this migration of white Southerners to the North Side, seeking work at small manufacturing plants,” Guarino said. “Unfortunately, the living conditions in Uptown were getting worse and worse.” Rather than staying indoors during hot summer weather, Uptown’s Appalachians spent time out on the streets and its neighborhood musicians played country tunes.

Like the West Side’s Skid Row, Uptown was “cleaned up” by urban renewal projects pushed by Richard J. Daley’s administration, including the construction of Truman College. “That meant all the people who lived there had to go,” Guarino said. Some residents protested, and local organizations, including the Old Town School of Folk Music, tried to preserve the neighborhood’s Appalachian culture, but it was a losing battle.

Under the watchful eye of the FBI

Guarino notes that the Old Town School is a big part of what sets Chicago apart from other cities. Of course, many places around the country offer music lessons, but no other school has lasted so long or played such a prominent role in fostering a city’s musical community.

One of the most eye-opening sections of Guarino’s book details the FBI surveillance of Win Stracke and Dawn Greening, who founded the Old Town School with Frank Hamilton in 1957. Stracke, who’d performed on television shows, lost that TV work when he was blacklisted. A witness told the House Un-American Activities Committee that Stracke belonged to a “Communist Party group which was connected with the entertainment industry.”

Greening was suspicious in the eyes of J. Edgar Hoover’s agents because she hosted touring musicians at her house, including folk singer Odetta. “Their home on Lombard [Avenue] in Oak Park became like a halfway house for musicians who were coming in,” Guarino said. “A lot of them were Black and wouldn’t feel welcome anywhere.” Guarino’s book quotes an FBI report on Greening: “Many of her neighbors had said unkind things to her, and that one time a member of the township government had visited her to talk to her about ‘town policy’ concerning Negroes and Jews.”

In spite of those suspicions from federal authorities, Stracke and Greening succeeded in creating an important gathering place for musicians. Guarino quotes a 1969 interview with Stracke, who died in 1991: “Folk music doesn’t belong to Black folks or white folks or blue folks, it belongs to people.”

Robbie Fulks, one of the musicians who hooked Guarino on alt-country back in the 1990s, wrote a foreword for Country and Midwestern. In it, Fulks praises the book for setting “the record straight on Chicago country with balanced perspective.”

It all happened, Fulks writes, right in “America’s biggest hick town.”

Robert Loerzel is a journalist based in Chicago. Archival photo research provided by WBEZ’s Justine Tobiasz.

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Want more? Country & Midwestern author Guarino offers this quick online video tour through Chicago’s roots history.

• Here’s a 1970 recording of John Prine at the Fifth Peg, a long-gone coffeehouse in Old Town where he had his first shows. 
• Win Stracke, the founder of the Old Town School, sings an original song about the 43rd Ward (Old Town) here.
• Special Consensus made this video about the WLS Barn Dance.
• Bradley Kincaid, one of the earliest country stars, sings “Barbara Allen,” a song he popularized in 1930.
• The Handsome Family, which formed in Chicago, performs “So Much Wine” here.

• Andrew Bird sings “Pulaski at Night,” arguably his most ‘Chicago’ song.