Early career (2020–2021) While awaiting the completion of a customer's build at his stepbrother's establishment, Bailey recorded himself singing "
Stay" by
Black Stone Cherry for
Snapchat to "impress girls". Songwriter Gavin Lucas, whose father had been Bailey's school bus driver in elementary school, came across Bailey's story and was taken aback by his singing ability. Lucas informed Bailey that the video had been widely shared, and he expressed interest in hearing some of Bailey's own songs. Several weeks later, while at his uncle's body shop, Lucas approached Bailey with a request to collaborate on a song. In response, Bailey penned the first verse of "Never Comin' Home." Subsequently, they captured a video of Bailey performing the song with Lucas accompanying on guitar. In December 2020, Zimmerman started sharing original music on his TikTok account, notably featuring "Never Comin' Home." Within a mere five hours, a snippet of the song had garnered over a million views. Motivated by this rapid success, he secured a studio in
Nashville to professionally record the track, investing $3,000. He made the decision to resign from his job shortly after. With finances tight, he turned to his mother, requesting $1,500. He conveyed to her the escalating traction of his song and his aspirations to pursue a career as a Country singer. The co-manager at 10th Street Entertainment Scott Frazier came across Zimmerman on TikTok and subsequently introduced him to Core Entertainment principals Kevin Zaruk and Simon Tikhman. He later signed to Core Entertainment in August 2021. The same month, he performed his first show at "Rock The South 2021" with a backing band he only met three days prior to the performance.
Religiously. The Album. (2022–2024) His breakout single "
Fall in Love" was released on February 11, 2022, and reached number 29 on the
Billboard Hot 100 in October. This was followed by additional singles "
Rock and a Hard Place" and "
Where It Ends" in June and August 2022, respectively. with "Fall in Love" later charting at Country radio format. Zimmerman released his debut major-label project
Leave the Light On on October 14, 2022. It debuted in the top ten of the
Billboard 200 and
Canadian Albums charts. As a result of high demand, Zimmerman extended his headlining tour of the United States into the fall of 2022, with
Josh Ross opening his early 2023 dates. He made his
Grand Ole Opry debut on November 4, 2022.
Morgan Wallen announced that Zimmerman would be one of the opening acts for his One Night at a Time World Tour in 2023. On March 17, 2023, Zimmerman announced his debut album
Religiously. The Album., and it was released on May 12, 2023. He will support the album with the "Religiously: The Tour" across the United States, Great Britain, and Ireland in 2024, with
Josh Ross again joining him as an opening act. “Rock And A Hard Place” broke the record for the longest climb to the top 10 for a song by a soloist in
Billboard Hot 100 history.
Different Night Same Rodeo (2024–present) On February 23, 2024, Zimmerman released "
Holy Smokes" as the lead single for his second album which was previously teased through TikTok. It debuted and peaked at No. 54. Zimmerman would be featured on
the soundtrack for 2024 film
Twisters with his song "Hell or High Water." On June 17, 2024, Zimmerman created anticipation for his new track "
New to Country" by teasing it on social media platforms, following its use as pre-concert hype music. On October 18, 2024, he released "Holding On", as another single from his sophomore record
Different Night Same Rodeo. In January 2025, Zimmerman announced his "New To Country Tour," a 16-show summer tour across U.S. amphitheaters with
Dylan Marlowe and
Drew Baldridge joining him as openers. On February 14, 2025,
BigXthaPlug shared a snippet of his
country rap collaboration "
All the Way" with Zimmerman through his
Instagram. Zimmerman announced the release date for the song on March 25. It debuted at No. 4 on the Billboard Hot 100, giving BigXthaPlug his first top 10 hit and Zimmerman his second and highest peaking single to date. On April 21, he announced a duet with
Luke Combs called "
Backup Plan." They debuted the song live at the 2025
Stagecoach Festival, where they also filmed the music video. It debuted at No. 36, peaked at No. 30, and became his fifth number one on country radio. He announced his second album
Different Night Same Rodeo on July 8, 2025, via social media and during a live performance at Spotify House during
CMA Fest in
Nashville. Zimmerman continued to tease the release by dropping promotional singles "Comin' in Cold", "Ashes" with
Diplo, and "Chevy Silverado" in anticipation.
Different Night Same Rodeo debuted at No. 12 on the
Billboard 200 and No. 3 on Hot Country Albums with 31,000 units sold. He announced his first-ever arena tour, the
Different Night Same Rodeo Tour, in support of the album for 2026. "Chevy Silverado" would be chosen as the third single for the album on October 13, 2025. == Artistry ==