It's hard to believe that at one time, Kenny Chesney played in a bar in Brownwood, Texas on his 30th birthday and no one came.
"It happened," Chesney assured Billboard's Ray Waddell in an interview at the annual Billboard Country Music Summit, held in Nashville Monday and Tuesday (June 6-7). "Radio was playing my record, but people had not yet associated me with my music."
Video: Kenny Chesney Q&A at Billboard Country Music Summit
The native of Luttrell, Tennessee, says there was never a time when music wasn't around him: his mother singing in the kitchen, the music at church, or the duo of his mother and her sister, Karen and Sharon, who performed locally in East Tennessee.
It wasn't until the four-time CMA Entertainer of the Year was in college that he decided music was a career possibility. "I had always looked on music as something that was just there, never something I'd do for a living," the singer confessed. "Then one day in my Persuasion class, I decided to write a song to try to persuade this girl to go out with me. I don't even remember the title, it was a bad song, but it was when I realized there might be something there."
After his move to Nashville in the early 1990s, Chesney parked cars and worked for a telemarketing company before associating himself with Acuff-Rose Music Publishing, where he wrote with songwriting greats Whitey Shafer, Dean Dillon and Skip Ewing. His first album, for eclectic label Capricorn, didn't do very well, but after he joined the BNA family things started to happen for him.
Chesney is the first to admit that in those early years, he was trying to be someone he was not, namely one of his heroes, George Strait. The Brownsville experience caught his attention, and around mid-2000, the singer/songwriter realized that he had to write, record and be more Kenny Chesney.
"I realized that I had to get better and better in everything I did. I wrote down 30 things I could do to make myself better and the next day I started doing them. We were getting airplay, we were selling records, but I felt that no one knew me. Once I started writing honest songs about myself, my life in East Tennessee and my life on the Islands, that's when my life changed."
Chesney is known very well for his annual tours, which generally include six to eight stadium shows. He says he got the idea for the stadium extravaganza when he toured with Strait early in his career.
"I was the second act up, after Asleep at the Wheel," he remembered. "Then there was the Dixie Chicks, Faith Hill, Tim McGraw and George, all in one day. I'd do my show, go shower and then come back and watch everyone else from the side of the stage. Doing that tour was the first moment I realized, 'Wow, this is how it's done.' And I vowed this was what I would do."
Chesney's shows have become day-long events for his fans, and at one time he would go out in the parking lot in a golf cart, surprising them by bringing out margaritas and taking time to chat. He doesn't do that as often now, but it made a huge connection between him and the people who crowd into his performances, which they have come to expect to be extraordinary.
"Either you can connect with people or not," Chesney said, acknowledging that it took him a while to be able to connect with the people on the top row of his stadium shows. "I was okay on making an arena feel like a club, but it was harder to make people in a stadium feel like they were in an arena."
Chesney hit on the idea of going up to the top tier of the stadium after he completed sound check, just to take stock of how far it was from that sat to the stage. "I would sit there and make a mental note, 'This is how far I have to go to reach this fan.' That's when I started learning how to make the stadium shows work."
The singer says his fans are reflective of himself as a person. "They are passionate, fun loving, music lovers, who love their family. They don't just listen to the songs, they live them," he described them. "I've always lived by the creed 'Work hard, play harder.' They reflect my attitude."
Chesney took off in 2010 from touring, but he worked on several projects, including three film presentations and his album, "Hemingway's Whiskey." He says the album was better because of the time he was able to spend on it.
"I had finished an album for the label in 2009, because I didn't want to have to do it when I was taking off," he admitted. "We finished editing it and I was driving home, listening to it, and I knew wasn't the album I wanted to release. We only used three songs off of it, one of them being 'Boys of Summer.' I immediately started looking for some more great songs."
The man who had been on the road since 1993, with no breaks, admitted that it was hard to take that year off. He had promised himself, however, that if he ever had doubts that he was delivering his best performances, he would take some time. That came in 2009, and when it did he was true to his promise.
"I realized I need to protect the investment that me, my team and my fans had put into my career," he said. "I could have hit it hard for a few more years and retired, but that's not what I wanted to do.
"I hope I've not written the best song or done the best performance I'll ever do. I want to continue to get better."
"When we put a tour together, the most important thing is to give our fans the best show I can for the least amount of dollars they have to spend to buy tickets, and me still make something. I try to find that balance, and make it worthwhile for everyone who comes to the show.