Shaboozey says that he immediately knew the verse “Me and Jack Daniel’s got a history” in “A Bar Song (Tipsy)” would resonate with fans. “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,’” Shaboozey recalls of the recording session for his crossover smash hit. The song would go on to spend 19 weeks at No. 1 on the Billboard Hot 100 chart, tying the record for longest run ever, and has over 1.4 billion Spotify streams. Shaboozey even partnered with Jack Daniel’s on their Highway No. 7 music series, a collaboration he hadn’t anticipated when writing the lyric. The country star launched his headlining Great American Road Show tour on Monday (September 22), and joining him is opening act Kevin Powers, the first artist signed to Shaboozey’s new label, American Dogwood, which he founded to support emerging Virginia artists. (People)