As the sun set in the heart of old Key West, Florida, a self-proclaimed pirate rode his rusty bicycle to the Blue Heaven restaurant to meet a friend—a friend we had just chatted with. “She said come in!” David Wegman laughed as he joined Kenny Chesney.
But here's the thing about Chesney – he's not really a country music superstar here. He's just another laid-back local. “We know a lot of the same people,” Chesney laughed.
He collects characters like shells—he met Wegman at Ivan's Stress-Free bar in the British Virgin Islands. “Above the counter it said in shells, ‘No shirt, no shoes, no problem,’” Wegman recalls.
The 2002 song “No Shoes, No Shirt, No Issues” helped Chesney become one of the most popular touring acts. Almost every summer he turns stadiums into beach parties. Among his many awards: 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 remarkable achievement he credits to this tropical turn in his career.
“You know what's crazy?” – he said. “I had a Greatest Hits album with 18 songs and no one knew who I was. They knew the songs, but I didn't feel comfortable in my skin yet. I didn't yet know who I was supposed to be as an artist. I'd go to concerts and they'd say, “Oh yeah, that's the guy who sings that song.” And then: “This is the guy who sings What song.' When I started being myself, that's when everything changed.”
He could take us to some Tiki bar in the Keys to support 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, “This space is almost like a sacred place.”
“Yes, can you feel it? I can feel it,” Chesney said. “I spent so much time, almost two weeks on the bow of my boat in the Virgin Islands, reading these books.”
This might explain why he came here to work on his first book coming out next month: “Music of the Heart” “This book gave me pause,” he said.
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Despite his love for the islands, he writes that it was his own mother who first realized that he might have strayed too far from his East Tennessee roots. “She wanted her 12-year-old boy back, but he left. Gone, gone,” he said.
“Was it difficult for her to find you, difficult to contact you?” I asked.
“I was kind of stung by it, but I was already so caught up in finding adventure and all this and all these new things going on in my life that I brushed it off.”
He continued to tour, continued to write, until a concert in Indianapolis in 2009, which he describes as hitting a wall and crying on stage. “At that point I was so exhausted and numb from it all that it didn't bring me happiness,” he said. “I created differently. I didn't communicate with the public. It just amazed 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” came his way, he didn't just record it; he began interviewing coaches and players about sports and life and turned it into an ESPN documentary, “Boys of Fall.” “I needed Joe Namath, I needed Bill Parcells,” he said. “I was sitting in Bobby Bowden's living room and he was talking to me like a deacon in a Baptist church! One day I woke up and went: I'm back“
Now he's the one doing the pre-game pep talk backstage, like at The Circle in Las Vegas. Many of his team have been with him for decades. There is confidence in the acquaintance. “If I had to sit on the bus and think about what I'm going to do, it would be… yeah, I'm not very good at it,” he said.
He put on the show his fans expect – a kaleidoscope of sand, sunsets and songs.
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When I met him the next morning he was still I’m discussing a speech in the Sphere. “The first couple of nights I found myself singing the song and thought: Well this is so cool! And then I forgot the words to the song I wrote!”
Joining him on stage that night was Grace Potter, the singer-songwriter he invited for a duet, although country isn't really her thing. Now they are friends for life.
“There are people who have always seen him as the iconic David of country music,” she said.
“I will go to Florence and stand next to her!” he laughed.
“But there’s a lot more to it than the sculpture itself,” Potter added.
Indeed, Kenny Chesney is a more complex guy behind the scenes, more thoughtful, even a little shy, if you can believe it. It's a part of East Tennessee that will always remain, even when he's chasing sunsets.
Chesney said, “It takes a certain ego to be on stage and do what I do, right? But I'm trying really hard to leave that person there. I can't live with this person every day. And I don’t want this person in my life every day, but I’m very excited to meet him when I get back there.”
READ REST: “Heart Life Music” door Kenny Chesney with Holly Gleason
WEB EXCLUSIVE: Extended Interview – Kenny Chesney (Video)
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The story was produced by Aria Shavelson. Editor: Remington Corper.
See also:
Kenny Chesney sends love to Boston bombing victims (“Sunday Morning”)
