Kenny Chesney on Why He Works So Hard: ‘I’m Terrified of Being Complacent’

Kenny Chesney is still one of the hardest-working artists in country music, something he has maintained for over three decades. By now, he is more than able to rest on his laurels, and follow the same formula show after show, album after album. But for Chesney, that has never, ever been an option.

The 56-year-old just released his BORN album, and will embark on his Sun Goes Down Tour on April 20, playing stadiums all over the country, including an unprecedented three nights at Gillette Stadium in Massachusetts to close out the tour. For Chesney, it’s the only way he knows to keep giving fans the best of himself that he can.

“I’m terrified of being complacent, and failure,” Chesney admitted on Today’s Sunday Sitdown with Willie Geist. “We always get into a stadium market on a Friday, and on a Friday after sound check, I’ll go to the very top and sit just by myself. I want to be grateful for what’s happened, and just reflect on all the years to get to this spot.”

Chesney also likes to sit at the top so he can understand what those fans will see during his show, assuring that everyone will get the best of him night after night.

“If I’m going to get close to connecting with these people, I’ve got to have their perspective,” Chesney explains. “So if you wanna find me on a Friday night, I’m probably sitting up [top] alone, thinking about what I’ve got to do the next night and just taking a moment to reflect and remember how grateful I am to be there,”

It took Chesney four years to make BORN, wanting to make sure it was the very best album that he could create, and hoping those songs translated to his live show.

“Without even knowing it, a lot of this record was made with the idea of people getting off their couch and feeling alive,” Chesney shares. “If I open the show with a song, it ramps to a place where it’s just on after that.”

Chesney’s first single, “Whatever It Takes,” was released in 1993. That song failed to crack the Top 40, and it took him four more years, and nine more singles, until he had a No. 1 hit, with “She’s Got It All.” But it wasn’t until the early 2000s that his superstar status was sealed, and no one — not even Chesney — could have predicted in the early years how far his career would take him.

“Once I started to get really genuine and authentic about what I did, that’s when it all changed,” reflects the singer. “What a concept … I just think it was a natural progression of growing up, and becoming different, and having more to write about.”

Chesney believes it’s his No Shoes Nation fan club that deserve much of the credit for his success, and perhaps the accomplishment that he is most proud of.

“It is a community,” Chesney boasts. “If it was just a party, we wouldn’t have kids here. We wouldn’t have families bringing their kids here. What we try to bring to the audience every night is the antidote in many ways of what they get on TV, from the news, whatever it is, all the devices.”

Chesney went from playing at a local Mexican restaurant in Knoxville to selling out stadiums all over the country. But to him, he’s still the guy playing for tips and free food that he was more than three decades ago.

“In ways, I still feel like I’m doing the same thing, I just got a lot more stuff around me,” he reflects. “You know, the interaction is still the same, but it’s just with a lot more people.”

Zac Brown BandMegan Moroney and Uncle Kracker will join Chesney as the opening acts on his Sun Goes Down Tour. Find BORN and all of Chesney’s music and tour dates at