Just as the sun was going down in the heart of old Key West, Florida, a self-described pirate rode his rust-ravaged bike to the Blue Heaven restaurant to meet a friend – a friend we just happened to be in the middle of interviewing. “She said come in!” David Wegman laughed, as he joined Kenny Chesney.

But that’s the thing about Chesney – down here, he’s not really a country music superstar. He’s just another laid-back local. “We know a lot of the same people,” Chesney laughed.

He collects characters like seashells – he met Wegman at Ivan’s Stress-Free Bar down in the British Virgin Islands. “Above the bar was written in shells: ‘No Shirt, No Shoes, No Problem,'” Wegman recalled.

That 2002 song, “No Shoes, No Shirt, No Problems,” helped make Chesney one of the biggest touring acts around. Almost every summer he turns stadiums into beach parties. Among his many accolades: the Academy of Country Music’s Entertainer of the Year Award, which he won four years in a row. And just last week, he was inducted into the Country Music Hall of Fame – a career-topping accomplishment that he credits to taking that tropical turn in his career.

“You know what’s crazy?” he said. “I had an 18-song Greatest Hits album, and nobody knew who I was. They knew the songs, but I wasn’t comfortable in my skin yet. I didn’t know who I was supposed to be as an artist yet. I would go do shows and they would go, ‘Oh yeah, that’s the guy that sings that song.’ And then, ‘That’s the guy that sings that song.’ When I started being my true, authentic self, that’s when everything changed.”

He could have taken us to some Tiki bar down in the Keys to keep up his tropical brand. But instead, he wanted to show us the room where Ernest Hemingway worked on “To Have and Have Not” and “Green Hills of Africa.”

I said, “The space, it’s almost like sacred place.”

“Yeah, do you feel it? I feel it,” Chesney said. “I spent so much, almost two weeks straight on the bow of my boat in the Virgin Islands reading those books.”

Which might explain why he came down here to work on his first book, out next month: “Heart Life Music.” “This book forced me to pause,” he said.

For all of his love of the islands, he writes it was his own mom who first realized that he may have drifted too far from his East Tennessee roots. “She wanted her 12-year-old boy back in ways, and he was gone. Gone gone gone,” he said.

“She had a hard time finding you, kind of had a hard time reaching you?” I asked.

“It hit me a little bit, but I was so already so addicted to seeking an adventure and all of it, and all these new things happening in my life that I dismissed it.”

He kept going, kept touring, kept writing, until a concert in Indianapolis back in 2009, which he describes as hitting a wall, and crying on stage. “In that moment I was so exhausted and numb to all of it, that it wasn’t making me happy,” he said. “I wasn’t creating the same way.  I wasn’t connecting to the audience. It just hit me.  It took sports to get me out of that funk.”

He grew up playing baseball and football – loving every inning, every down. So, when a song called “The Boys of Fall” crossed his path, he didn’t only record it; he began interviewing coaches and players about sports and life, and turned it into a documentary for ESPN, “Boys of Fall.” “I needed Joe Namath, I needed Bill Parcells,” he said. “I sat in Bobby Bowden’s living room and he talked to me like a deacon in a Baptist church! I woke up one day, and I went, I’m back.”

Now he’s the one doing pre-game pep talks backstage, like at Sphere in Las Vegas. Many on his team have been with him for decades. There’s confidence in familiarity. “If I had to sit on the bus and think about what I’m getting ready to go do, it would – yeah, I don’t do well with that,” he said.

He put on the kind of show his fans expect – a kaleidoscope of sand, sunsets and songs.

When me met him the next morning, he was still buzzing about performing in Sphere. “The first couple of nights, I caught myself singing a song and I was like, Well, this is so cool!  And then, I forgot the words to a song that I actually wrote!”

On stage with him this night was Grace Potter, the singer-songwriter he recruited for a duet, even though country really wasn’t her thing. The two are now lifelong friends.

“There’s people who have always seen him as just the iconic, you know, Statue of David of country music,” she said.

“I’m gonna go to Florence and stand beside it!” he laughed.

“But there’s just so much more underneath it that’s more interesting than the sculpture itself,” Potter added.

Indeed, the off-stage Kenny Chesney is a more complicated guy, a more thoughtful guy, even a little shy if you can believe it. That’s the East Tennessee part that will always remain even as he’s chasing sunsets.

Chesney said, “It takes a certain amount of ego to be up there on stage and to do what I do, right? But I try really hard to leave that person up there. I can’t live that person every day. And I don’t want that person in my life every day, but I’m really glad to meet him when I go back up there.”

READ AN EXCERPT: “Heart Life Music” by Kenny Chesney with Holly Gleason

WEB EXCLUSIVE: Extended interview – Kenny Chesney (Video)

     
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Story produced by Aria Shavelson. Editor: Remington Korper. 

      
See also: 

Kenny Chesney spreads the love to Boston bombing victims (“Sunday Morning”)