HENRY DILTZ PHOTOGRAPHY MEDLOCK KRIEGER 2018

Jason Scheff on Stepping Into Legacy, From Chicago to Happy Together 2026 Tour

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Jason Scheff didn’t plan on joining the Happy Together tour this year, but when the call came, he says there wasn’t much of a decision to make. “I’ve known the producers of the show for several years doing other productions, and they called me as Mark Volman of The Turtles had become very ill,” Scheff explains. “I feel very connected to all of the artists on this show, so I felt an immense sense of service and duty when they called.” It’s a familiar feeling for him — the same one that led him to Chicago decades ago. “Just like when I joined Chicago, I heard the calling to be a part of the extension and legacy of this incredible brand they’ve built.”
That sense of musical lineage runs deep for Scheff, and it traces back further than his own career. Among the acts on the Happy Together bill, it’s Ron Dante’s music that first hooked him as a kid. “The first song that captivated me on the radio, that had my ear glued to it waiting for it to play again, was ‘Sugar, Sugar,’” he says. “I’d have to say that was ground zero for me being hooked on music, the radio, and all of this that we do today in music.”
Thirty Years in Chicago
Last year marked the 40th anniversary of Scheff joining Chicago — a milestone he still finds hard to believe. “Can you believe that? 40 years?!” he says. “When I joined Chicago, I thought it would never last. The thought of stepping in to replace an icon such as Peter Cetera was just something I couldn’t wrap my head around. I just kept going until I crashed and burned — but I didn’t.”
Instead, he hit the ground running, singing lead on one of the band’s biggest hits, “Will You Still Love Me,” right out of the gate. “It cemented my place in the band and its legacy,” he says. The scale of what followed caught even the people closest to him off guard. “The funny thing is, my publisher, who got me to them at the beginning, said, ‘This is amazing! You’re going to get a good five years out of this!’ Well, we surpassed that by another 25.”
With a catalog as deep as Chicago’s, and festival-style sets running short on the Happy Together tour, choosing a setlist comes down to knowing the room. “You just play the songs that are pretty universal,” Scheff says. “The audiences aren’t there to just hear Chicago, so you’ve got to play songs that everybody has heard a lot. Fortunately, there are so many iconic hits in the catalog, it’s not hard to pick four that everyone has loved for almost 60 years now.”
A Musical Inheritance
Scheff’s path into music was shaped early, growing up as the son of a bassist who played alongside a long list of iconic artists. One memory in particular stands out. “My father took me to a recording session once he played on for Bobby Vinton — it was the Wrecking Crew on the date,” he recalls. “I’ll never forget meeting this little man with a goatee conducting a small string section. His name was Jimmy Haskell.” Haskell, as it turned out, wrote many of the era’s most iconic string arrangements, including the one for “If You Leave Me Now.” Looking back, Scheff sees it as one of several early signs pointing toward the life he’d eventually live. “When I sit back and reflect on how the seeds are planted along the way in our lives, and you look back and see the story that was unfolding and see the clues, it’s pretty astounding.”
What’s Next
Beyond the Happy Together tour, 2026 is shaping up to be a busy year for Scheff. He’s got dates lined up with the Jason Scheff Band, as well as Generation Radio, his project with longtime friend Jay DeMarcus of Rascal Flatts. Fans can keep up with both at jasonscheff.com.

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