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The first time Alynda Segarra met John Prine was in an airport. “I heard a voice behind me, and I was like, ‘That’s fucking John Prine,’ ” recalls the 39-year-old musician, best known for founding the indie folk band Hurray for the Riff Raff. The legend was chatting with a stranger about — of all things — mayonnaise brands. Segarra introduced themself. “He told me that his wife had heard of my band,” Segarra says. “That’s how I get a lot of people. They’re like, ‘My wife loves you.’ ”

Back when Segarra was a “traveling punk kid,” they’d often hear Prine’s “Paradise” sung around the campfire or played by buskers. “It was really like an anthem. And once I started diving into his catalog, ‘Sam Stone’ is the song that really hit me,” Segarra says, leaning forward to steal glances at the jukebox at the Old Town Ale House, one of the late Prine’s frequent postshow hangouts. “I always know when I’m around a John Prine fan — they are obsessed with the craft of song.”

Segarra will be joining Amos Lee, Margo Price, Steve Earle, and a slew of other Americana musicians, plus host John C. Reilly, for a concert celebrating what would have been Prine’s 80th birthday. It’s the headline event of a five-day festival honoring the illustrious Old Town School of Folk Music alum, who died in April 2020, just a few months after receiving a Grammy for lifetime achievement. For Segarra, being part of this singular lineup, backed by Prine’s longtime live band, feels like being part of his lineage.

Since relocating to Logan Square from New Orleans two years ago, Segarra thinks a lot about moving through the same spaces as Prine: “I imagine who he saw when he was stomping around the city, and the different influences you wouldn’t expect that made an impact on his songwriting.” Sometimes they worry that Americans’ personality quirks are getting flattened out of us. When that happens, Segarra says, “I turn to Prine’s music as a celebration of those people, these unsung heroes.”

Segarra performs at Souvenirs: 80 Years of John Prine on October 8 at the Chicago Theatre.

Sarah Steimer is the contributing 312 and digital editor at Chicago magazine.

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The Nightmare Maker
The Graphic Stenographer
The Hip-Hop Historians
The Crafty Activist
The Hope Messenger
The Inadvertent Soothsayer
The Soul Searcher
The M.A.D.D. Men
The Daring Director