Shaboozey Knew This Line in ‘A Bar Song (Tipsy)’ Would Be a Hit (Exclusive)

Shaboozey got his big break in 2024 with “A Bar Song (Tipsy),” and one lyric in particular quickly became a fan favorite.

In the chorus of his hit song, the country singer, 30, sings, “They know me and Jack Daniel’s got a history.” It’s a line sung loudest by fans — something Shaboozey knew would happen. 

“I remember writing the record and just thinking about ways that I could put more of myself in there, and being that I enjoy Jack Daniel’s, I thought it made so much sense,” the five-time Grammy nominee tells PEOPLE. 

“I remember running that line and everybody in the room being like, ‘Oh, that’s the line — that’s the line everyone’s going to gravitate towards and really connect with.’ The fact that there’s something in there that I feel like is personalized and is a part of me in the song is really awesome.”

The song went on to spend 19 weeks at No. 1 on the Billboard Hot 100, holding the record — along with Lil Nas X and Billy Ray Cyrus‘ “Old Town Road” — for the longest run. It also has more than 1.4 billion streams on Spotify. 

The “Last of My Kind” singer performed in New York City as part of Jack Daniel’s Highway No. 7 cross-country music series Saturday, Sept. 20. He tells PEOPLE it was “really cool” he could align with the whiskey brand. 

“I kind of [wrote the line] without thinking that there would be a partnership later down the line. But ultimately it happened,” he says. “It’s just been awesome. They’ve been a huge part of my story so far, my journey so far, and have been a huge support in everything we do. It’s just awesome. I love the Jack family.”

The concert was a sneak peek for fans at what they can expect as he kicks off his 12-stop U.S. tour, The Great American Road Show, this week.

“This will probably be a year out of touring. So after doing so many shows and seeing so many fans, I’ve gotten a better idea of how I want to enhance the show. It’s gonna be really fun,” he told PEOPLE.

Joining him on tour as his opening act is fellow country singer Kevin Powers. Last Friday, the two released their first collaboration together, “Move On.”

“He’s super talented, and I’m excited to get on the road with him,” Shaboozey says of Powers. “He’s young, energetic and funny. So I’m just really happy to have him on the road … I can’t wait to see how people receive the show. We worked really hard on it.”

Powers is also the first artist signed to the Virginia native’s new record label, American Dogwood.

“He’s awesome. He’s one of the most talented people I’ve really ever met in music,” Shaboozey says of the singer. “I remember being stuck on some parts, and Kevin would knock it out in 10 to 15 minutes.”

The “Good News” singer added that starting his own record label was something he has always wanted to do, especially growing up in Virginia, where there weren’t too many places for up-and-coming artists to connect. 

“There wasn’t really a place or a home for any of us to network in the industry or to connect with [others]. So for me, it was about being that platform and being that bridge,” he explains. “I just wanted to really create a home for people like me who maybe needed that support, or needed to find that platform for us to get our voice and our stories out there.”