“This Version of Me Would Not Be the Same Without the Struggle”: Kenny Chesney Recalls Playing Nashville Bars for Tips Before He Found Success

Kenny Chesney had to work hard to find success. The country star took ABC on a tour of Lower Broadway, the famed area of Nashville where he used to play in bars for tips.

Videos by American Songwriter

“I sat on a stool a lot like this one, and I sat and played four hours a night with a tip jar in front of me,” Chesney said while visiting Tootsie’s Orchid Lounge. “It taught me a lot about performing, because every crowd is different. It was a master class in giving the audience what they want.”

Later in the interview, which will air during ABC’s Center Stage: Countdown to the CMA Awards on Nov. 18, Chesney spoke about how Downtown Nashville has changed since those days.

“It was the Nashville and the Lower Broadway that Willie Nelson and Kris Kristofferson, when they were struggling songwriters, that they saw,” he said. “I feel very fortunate that I got to see that before it all changed.”

Kenny Chesney Looks Back on His Career

After his time in the bar scene, Troy Tomlinson signed Chesney to a songwriting deal. That soon turned into a recording contract.

“I’m so thankful for that time because this version of me would not be the same without the struggle,” Chesney said, “and the struggle is what makes you better.”

Chesney’s “life exploded” in 2002 when he released his sixth LP, No Shoes, No Shirt, No Problems.

“It’s like an out-of-body experience,” he said of experiencing huge success. “You’re so connected to a group of people, it’s like an avalanche that you can’t stop.”

Chesney’s career continued from there, and culminated with his recent induction into the Country Music Hall of Fame.

“It didn’t really hit me until I walked into the rotunda that night and we took a group picture of all the living members, and I was in the picture,” Chesney said. “And for me to have my face right there on that wall in this rotunda with a lot of the people that were the best of the best, it means everything to me.”

That honor and all of the others Chesney has received turned his once “big dream” into reality.

“It’s this kid that laid in the backyard of his grandmother’s house that would look up at the sky at night and wonder if there was anything out there,” he said. “And if you’d have told that kid that dream would’ve developed into this, I would’ve told you you were crazy.”

Photo by Carly Mackler/Getty Images