Bailey Zimmerman spoke about why he placed the “craziest” bet on himself when he opted to pursue his career in music — and how his mother played a life-changing role in making it happen.
Zimmerman, 25, admitted he “had never even thought about doing music at all,” when he caught up with Kyle McMahon on a recent episode of Pop Culture Weekly. “It was never in the cards. I didn’t come from a musical family. I didn’t sing in church. I’d never sang in my life before TikTok.”
Now hit-making singer-songwriter, Zimmerman said he began singing “in secret” after a few friends around a campfire complimented his voice. “And from the time somebody told me, ‘hey, your voice is cool,’ to the time I released my first song was probably like two months,” the former construction worker recalled. He first shared a clip of himself singing on Snapchat, admitting that at first, he thought he might catch a girl’s attention. Instead, a friend from his hometown, Gavin Lucas, reached out to tell Zimmerman that he’d been writing music. The duo quickly decided to meet up, which lede to Zimmerman’s TikTok that surpassed more than a million views overnight.
“That morning is when I was like, ‘I’m gonna figure this out.’ I had been praying a lot about what my purpose was, and praying to God to give me something to chase… and since then, I have not let up,” Zimmerman recalled. “I went to my mom and I was like, ‘OK, this is gonna be a shock. But I quit my job and I’m gonna do music.’
“It’s crazy to look back now on all that because it’s like, dang, all this stuff happened, and my mom investing $1,500 into me and just, that part of life was so much fun because it was like that moment where I was like, ‘I’m gonna chase this and there’s nobody gonna change my mind. I’m not doing anything else. I’m gonna do this,’” he said, referencing the money he needed to record a song for the first time. “That was the craziest ride.”
Zimmerman said although he’s been on a “meteoric rise,” as McMahon noted during their conversation, “there is a grind to it.
“I have had to grind every single day for the last five years since I had that opportunity. I have not slept. I’m constantly working. But at the same time, I’m so blessed and I’m so fortunate to have a dream to chase, have opportunity every single day,” he explained. “I had a job that I hated and I was grinding, working my a** off every single day, and the heat, and it just, so now every single day I wake up, dude, and I get to go into an air conditioned room and write songs and get to do what I do. ...I’m blessed. I’m grateful just to be here.”
Throughout their conversation, Zimmerman shared why he feels songwriting is “therapeutic,” how he’s grown from “some ups and downs,” how he scored collaborations with powerhouse artists (including one of his latest with award-winning country star Luke Combs), and more.
Zimmerman is gearing up for his headlining “Different Night Same Rodeo Tour” in 2026. The run of shows — titled after his highly-anticipated sophomore record that released last month — marks “my first time playing arenas.” Special guests Hudson Westbrook and Blake Whiten will make up the lineup “to help make sure that this tour is one for the history books.” See the list of tour stops below. Tickets will be available on Friday (September 12) at 10 a.m. local time.
Find Zimemrman’s full conversation with McMahon on iHeartRadio here.
DIFFERENT NIGHT SAME RODEO TOUR 2026
Thu, Feb 19 – Estero, FL – Hertz Arena
Sat, Feb 21 – Athens, GA – Atkins Ford Arena
Thu, Feb 26 – Greenville, SC – Bon Secours Wellness Arena
Fri, Feb 27 – Knoxville, TN – Thompson-Boling Arena at Food City Center
Sat, Feb 28 – Pikeville, KY – Appalachian Wireless Arena
Thu, Mar 5 – Boston, MA – TD Garden
Thu, Mar 12 – Grand Rapids, MI – Van Andel Arena
Fri, Mar 13 – Moline, IL – Vibrant Arena
Sat, Mar 14 – Evansville, IN – Ford Center
Fri, Mar 27 – Orange Beach, AL – The Wharf Amphitheater
Thu, Apr 2 – Fort Worth, TX – Dickies Arena
Fri, Apr 3 – Baton Rouge, LA – Raising Cane's River Center
Sat, Apr 4 – Corpus Christi, TX – Hilliard Center Arena
Thu, Apr 9 – Uncasville, CT – Mohegan Sun Arena
Fri, Apr 10 – Atlantic City, NJ – Hard Rock Live at Etess Arena
Sat, Apr 11 – Pittsburgh, PA – Petersen Events Center
Thu, Apr 16 – Toledo, OH – The Huntington Center
Fri, Apr 17 – Green Bay, WI – Resch Center
Sat, Apr 18 – Sioux Falls, SD – Denny Sanford PREMIER Center
Thu, Apr 30 – Huntsville, AL – Von Braun Center Propst Arena
Fri, May 1 – Nashville, TN – Ascend Amphitheater
Thu, Jun 4 – Airway Heights, WA – Northern Quest Amphitheater
Fri, Jun 5 – Nampa, ID – Ford Idaho Center Amphitheater
Sat, Jun 6 – Bend, OR – Hayden Homes Amphitheater
Wed, Jun 10 – Abbotsford, BC – Abbotsford Centre
Thu, Jun 11 – Kelowna, AB – Prospera Place
Sat, Jun 13 – Edmonton, AB – Rogers Place
Thu, Jun 18 – Toronto, ON – Budweiser Stage
Fri, Jun 19 – London, ON – Canada Life Place
Sat, Jun 20 – Ottawa, ON – Canadian Tire Centre