After building up a sizable following on TikTok, Bailey Zimmerman released his freshman record Religiously. The Album in 2023. And country audiences took notice, sending all four of the album’s singles to No. 1. The 26-year-old kept the momentum going with 2025’s Different Night Same Rodeo, which yielded his fifth No. 1 single in the Luke Combs collab “Backup Plan.” Last month, Zimmerman kicked off his Different Night Same Rodeo Tour in support of his sophomore record. Riding high after Thursday’s (March 5) sold-out show at TD Garden in Boston, the “Rock and a Hard Place” singer decided to pay it forward.
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Bailey Zimmerman Mingles With Boston Bar Crowd
Patrons at J.J. Foley’s, a popular bar in the city’s South End, were stunned when Bailey Zimmerman strode through the doors and requested “the best Guinness in Boston.”
The establishment was all too happy to deliver, said owner Mike Foley in a statement.
Zimmerman lingered long after satiating his thirst, posing for pictures and striking up conversations with patrons. Then, he surprised the crowd a second time by picking up the tab for everyone in the bar.
“That’s the kind of guy he is,” Foley said, calling the CMA Award-nominated artist “the real deal.”
Next, Zimmerman heads to Grand Rapids, Michigan, for a March 12 show. He will wrap up the Different Night Same Rodeo Tour on June 20 in Ottawa, Ontario, Canada.
[RELATED: “Got Back Up”: Bailey Zimmerman Reflects on Bouncing Back From Viral 2025 Mishap]
“I’m About to Cry”: Zimmerman Takes It All in During Knoxville Show
Bailey Zimmerman’s impressive rise in country music has not come without setbacks. In January 2025, he found himself at the internet’s mercy following an admittedly intoxicated performance at Luke Bryan’s Crash My Playa Festival in Mexico.
Publicly apologizing and committing to addressing his alcohol use, Zimmerman finished out the year strong. During a Feb. 27 stop at Thompson-Boling Arena in Knoxville, Tennessee, the Illinois-born artist paused onstage to reflect on his journey.
“A lot of words are coming to my head, but I’m about to cry,” Zimmerman admitted. “Because this is the fourth arena show on the Different Night Same Rodeo Tour. And we have 9,500 people here right now. I’d say that’s pretty good for the white boy from a trailer park!”
Featured image by Jon Kopaloff/Getty Images for Core Entertainment
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