Kenny Chesney talks rise to stardom and Country Music Hall of Fame
Country music superstar Kenny Chesney is opening up about his life and career.
The singer, a Tennessee native, was inducted into the Country Music Hall of Fame last month, marking the latest chapter of success as an artist, which he discussed in detail on "Center Stage: Countdown to the CMA Awards" airing on ABC Tuesday night.
"If you pull back from all of it, it's all just a big dream," he said, looking back at his career. "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. And if you'd have told that kid that dream would've developed into this, I would've told you you were crazy."
Chesney said during a childhood consumed by sports, music entered the picture in a prominent way. "Music was always in my life, but I didn‘t know it was going to be my life."
One pivotal moment that inspired him musically came during a Thanksgiving Day concert in Knoxville, Tennessee, featuring George Jones, Merle Haggard and Conway Twitty, leaving a young Chesney "numb watching them.”
Chesney got his start when he played for the East Tennessee State University Bluegrass band, saying the program "changed my life." While attending the university, Chesney began performing at local bars and restaurants, where he would play for tips and "all the enchiladas I could eat."
In 1991, Chesney moved to Nashville to pursue a career in music.
Visiting Nashville's Broadway district with ABC, Chesney described how the area has changed compared to his early days there. "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."
Troy Tomlinson, the country music executive that signed Chesney as a writer to Acuff-Rose, recalled the moment he realized Chesney was meant to be on stage. “Really early, honestly, after we'd signed him, we were doing demos and he was just singing them,” said Tomlinson. “An engineer named Bill Harris looked over at me and he said, ‘Troy, honestly think this guy could be a recording artist.’ And I said, ‘I'm thinking the same thing right now, Bill.’”
Tune into "Center Stage: Countdown to the CMA Awards — Special Edition of 20/20" on Tuesday, Nov. 18, at 10pm ET on ABC, and watch it streaming the next day on Disney+ and Hulu.
Chesney explained that a record contract didn’t mean instant success for him -- the road to stardom was not all smooth sailing. But, he wouldn't change those times, saying, "I'm so thankful for that time because this version of me would not be the same without the struggle, and the struggle is what makes you better."
Chesney said a big break arrived when he was invited to open for country music legend George Jones on tour, bringing his journey full circle from the night he watched Jones, awestruck from a Knoxville audience.
The Country Music Hall of Famer described a moment in his career with high-profile songs, but little to no name recognition, something that changed with the release of "She Thinks My Tractor’s Sexy."
"I always say that I was smart enough to record it and smart enough not to record another one," said Chesney of the hit. "But everybody needs one of those to rattle somebody's cage."
It was the Casey Beathard-written 2002 anthem "No Shoes, No Shirt, No Problems" that launched Chesney into superstardom and brought him a passionate fan base unlike any other.
"I was changing as an artist and as a creative person. And all that was evident when the 'No Shoes' album came out, and that's when my life exploded," Chesney said.
He described the burst of energy injected into his shows by his fan community, known as "No Shoes Nation."
"It's like an out-of-body experience," he said. "You're so connected to a group of people, it's like an avalanche that you can't stop."
While Chesney's career would continue to soar, he described the toll the success took on his life, which came to a head during a 2009 show in Indianapolis when the singer grew visibly emotional on stage, and was unable to get through a song.
He took the next full year off from touring to recharge.
"It was a necessity. I had invested so much of my life into the relationship, and I called it a love affair with the fans, but on the flip side of that, they have invested... so much of their life," he said. "And that investment, to me, on both ends, was worth protecting at all costs. And if that meant taking a year away, then that's what it meant," he told Robin Roberts in a 2011 interview.
After his hiatus, Chesney's career would pick up right back where he left off, with sold-out stadium shows and he was named Billboard’s No. 1 Country Artist of the 21st Century. His recent honors include an honorary doctorate from East Tennessee State University, becoming the first country music artist to headline shows at the Sphere in Las Vegas and induction into the Country Music Hall of Fame in 2025. Chesney's 2025 book "Heart Life Music" reached No. 1 on two New York Times Best Seller lists: Hardcover Nonfiction and Combined Print & E-Book Nonfiction.
"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 of the honor. "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."
Chesney finished, "I know there's a lot of kids out there that have that same dream that they don't even know what it is yet. And I am proof that extraordinary things can happen to an ordinary person, I promise you."
Tune into "Center Stage: Countdown to the CMA Awards — Special Edition of 20/20" on Tuesday, Nov. 18, at 10pm ET on ABC, and watch it streaming the next day on Disney+ and Hulu.
