When Bailey Zimmerman takes the stage to perform his brooding, multiweek Country Airplay chart-topper “Rock and a Hard Place,” the memories of a particularly bad breakup come flooding back to him.

“There was a girl I really loved. I wanted to give her the world and bought her a ring, and then she did some really messed-up stuff,” Zimmerman says. “Every time I see people cry during ‘Rock and a Hard Place’ when I’m singing it live, it takes me back to that moment. I remember being in my truck, screaming the lyrics to [Morgan Wallen’s] ‘Sand in My Boots’ because I was so sad and hurt. The line in ‘Rock’ about ‘We’ve been swinging and missing’ just resonated with me.”

When it comes to his career, Zimmerman (who is signed to Warner Music Nashville/Elektra Music Group) has been doing plenty of swinging — and making lots of contact. Now he’s not just screaming the lyrics to Wallen’s song: He’s opening the superstar’s stadium tour this summer. Less than four months after notching his first No. 1 on Billboard’s Country Airplay chart with “Fall in Love” in December, “Rock” reached the top spot, too. “Fall in Love” was still on its way to No. 1 when Zimmerman’s management team began seeding radio executives with the follow-up single.

“ ‘Rock’ checked all the boxes — great lyric, great melody, and it perfectly fits the direction Bailey is going,” says The CORE Entertainment co-founder/CEO Kevin “Chief” Zaruk, who co-manages Zimmerman with 10th Street Entertainment. “The feedback we received was that it would be an even bigger hit.”

The early stations that jumped on “Rock and a Hard Place” were prescient: The song (written by Heath Warren, Jacob Hackworth and Jet Harvey) achieved even more chart success than its predecessor, leading Country Airplay for six weeks. And in April, it became Zimmerman’s first top 10 on the all-genre Hot 100.

In less than three years, the 23-year-old native of Louisville, Ill., has gone from burgeoning TikTok star to bona fide hit-maker and, now, Billboard’s inaugural country Rookie of the Year. After high school, he began working on a natural-gas pipeline in West Virginia and gained a modest TikTok following for his videos of custom-lifted trucks. Singing was simply a hobby for Zimmerman until December 2020, when he uploaded a video of himself performing “Never Comin’ Home,” a song he had written with high school friend Gavin Lucas. The track went viral, and Zimmerman gave his union notice the following day.

“It was funny, because they were like, ‘You mean we should just take you off the schedule for a bit?’ And I was like, ‘No, I quit. I’m done,’ ” Zimmerman recalls. He continued writing songs and moved to Nashville to record, adding producer Austin Shawn to the core group of collaborators helping him craft his raw, unflinching brand of rock-tinged country. Zimmerman recorded in a spare bedroom in Shawn’s house, cutting his vocals in a small closet. “It’s the same room [where] I met Bailey for the first time, where we talked about lifted trucks and dirt bikes for about three hours straight,” Shawn says.

Zimmerman signed his co-management deal in 2021 and announced his label deal the following year. Now he’s one of several artists who have recently ascended swiftly from social media virality to packing venues. (The Neal Agency books his shows.) He’s acutely aware that he sidestepped years of the grueling club shows that typically pave the way to country stardom — and that his learning curve is happening publicly. A few months ago, a clip of him singing off-key live went viral, leading him to post an endearing video in which he apologized for sounding “absolutely awful” before launching into a sturdy a cappella version of “Rock and a Hard Place” to prove he had simply experienced an off night.

“You can say, ‘You didn’t have to go through the 10 years in the bars to get where you are at.’ At the same time, [those artists] had plenty of time to deal with things like your mic not being on or your [in-ear monitors] going out — they could learn all that in clubs,” Zimmerman says. “I had to learn it in front of thousands of people.

“The first two years were rough,” he continues. “I got [vocal cord] nodules and had to not talk for almost three months. My voice was so weak, and I had to build it back slowly — I never went hoarse for a show, thank God, and I never needed surgery. But my voice is stronger now, and I’ve learned how to take care of it.”

Not that Zimmerman has had much time to ponder his whirlwind success. Following its May 12 release, his major-label full-length debut, Religiously. The Album, entered the Top Country Albums chart at No. 3 and the Billboard 200 at No. 7.

“We’ve been working so hard, and to see the songs touching people like they have is amazing,” Zimmerman says. “And to be Rookie of the Year for Billboard is such a big deal. I can’t wait to call my mom — she’s going to freak.”

This story will appear in the June 3, 2023, issue of Billboard.