Chicago has earned its reputation as the iconic “rock and roll band with horns,” but in their early days, they encountered significant challenges. Surprisingly, their struggles were not primarily with critics, but rather with the music industry’s gatekeepers.

Their debut album, Chicago Transit Authority, released in 1969, is an ambitious double LP featuring nearly 80 minutes of diverse and experimental music. While such lengthy albums are commonplace in today’s digital landscape, in the late ’60s, this was considered quite excessive for a debut. Their initial singles faced radio resistance, with “Questions 67 & 68” peaking at No. 71 on the Billboard Hot 100, and its follow-up, “Beginnings,” failing to chart altogether.

As trumpet player Lee Loughnane, a founding member of the group, reminisces during a conversation on the UCR Podcast, radio programmers expressed that they couldn’t play their songs without prior hits. “They literally said that because we hadn’t had a hit yet, they couldn’t play the song,” he recalls, highlighting the frustrating paradox of needing airplay to achieve success. Critics praised their debut, proclaiming them as pioneers with immense potential, yet AM radio remained hesitant to embrace their music.

Listen to Chicago’s ‘Beginnings’

Despite their frustrations, the band remained committed to honing their craft through extensive touring. “We were playing schools and wherever else. We played everywhere across the country,” Loughnane remembers. As they worked on their second album, they rehearsed new material on stage, a process that culminated in their performances at prestigious venues like Carnegie Hall and the Kennedy Center. These live gigs served as critical opportunities to refine their songs before entering the studio. Reflecting on that period, Loughnane wonders, ‘How did we have the stones to try to pull that off?’ but acknowledges that touring was the only time they could work on their music, given their relentless schedule.

READ MORE: How Chicago Continued to Evolve in the ’70s

The release of Chicago & Friends: Live at 55 in late November captures the essence of the magic from their Chicago Transit Authority days. Recorded during two concerts in Atlantic City in 2023, this album showcases the band’s rich history and the remarkable performances that took place each night. Over the course of two sets, they performed 35 songs, creating a thrilling experience that lasted more than two and a half hours. While some covers were omitted, fans can now enjoy nearly the entirety of the performances.

Particular emphasis is given to the tracks from Chicago Transit Authority. Fan favorites like “Beginnings,” “Questions 67 & 68,” and “Does Anybody Really Know What Time it Is” remain staples in their setlists. The Atlantic City shows also featured rare gems such as “Listen” and “Poem 58,” which had not been played live since the ’70s. Renowned guitarist Steve Vai, a prominent admirer of the late Terry Kath, joined the band to perform “South California Purples,” marking its first live rendition since the early ’80s. Additional guest appearances by Robert Randolph and Christone “Kingfish” Ingram added even more excitement to these historic performances.

Listen to Chicago’s Performance of ‘South California Purples’ With Steve Vai

The Atlantic City concerts illustrate how the band’s music continues to evolve over time. This evolution parallels their journey from Chicago to California in the years preceding Chicago Transit Authority. Loughnane recalls, “We actually had no idea what was going to happen. We just went out there thinking that hopefully something will happen.” Initially, they performed covers of popular Top 40 songs, drawing inspiration from acts like Vanilla Fudge, who were known for their unique arrangements. This experimentation laid the groundwork for their distinctive sound, blending various musical influences into a cohesive style once they recorded their own material.

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According to Loughnane, there were no predefined sonic templates guiding their recording sessions for Chicago Transit Authority under producer James William Guercio. “I don’t know if we necessarily did it that way, other than have the songs rehearsed to the point where the writer would bring it in and then sort of turn it over to us,” he explains. As they played, ideas flowed naturally, allowing the band to shape the songs further. By the time they entered the studio, many arrangements were solidified, including the simultaneous recording of brass parts, which would later be re-recorded for final production. This method ensured consistency in the performance, regardless of any background bleed that might occur during recording.

Memorable Moments: Opening for the Legendary Jimi Hendrix

In 1969, the band achieved another significant milestone when they were invited to open a series of concerts for the iconic Jimi Hendrix Experience. Reflecting on those early performances, Loughnane acknowledges that while they had much to learn, they also recognized positive feedback from the audience.

“We went on first, obviously, and the audience was more interested in hearing Jimi, so there was a lot of ‘Put Jimi on stage’ chants,” Loughnane reflects. Despite the initial indifference, he believes that enough audience members appreciated their sound, thinking, ‘These guys aren’t so bad.’ On a relatively small 40-foot stage, they were accustomed to close quarters from club performances, which led to an intriguing visual dynamic. Loughnane notes that their tight formation on larger stages with Jimi Hendrix and Janis Joplin must have looked unusual, given their experience at the time.

Listen to Lee Loughnane on the ‘UCR Podcast’