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Kenny Chesney: An intimate backstage conversation with country's biggest star

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In the current issue of EW, you can find my “backstage pass” feature on the touring circus that is country superstar Kenny Chesney’s life. Over two days at Heinz Field in Pittsburgh, we captured the fans, the partying, the camaraderie amongst his staff, and the bombastic live show from every angle. (You can even see a picture of me packed into the box they use to roll Chesney into the audience for the start of the show). But there’s so much we didn’t have room to include that’s stuck with me after the two days I spent as a (relatively) sober fly on the wall in Chesney Land: He travels with a 235-pound stuffed blue marlin that he caught himself, for example; “Marley” serves as a sort of mascot, and a reminder not to take things too seriously out on the road. The tour has its own printed plastic cups, and goes through them at the approximate rate of a minor-league-baseball-stadium beer vendor. The Sun City Carnival employees travel with their own interior decorating, turning fluorescent-lit football locker rooms into moody lounges and tiki bars, installing a stripper pole in the production office (that reportedly very few people have dared to work), and commandeering one training area as the “Vibe Room,” intended as a place for friends (old and new) to come together before and after the show, raise a cold one, and relax. The answer to the question “Who lives like we do?” is “WE DO!”

But despite all the trappings of his phenomenal success — the screaming girls, the parking-lot mob scene, the chance to travel the world with your buddies by your side — it was the final conversation I had with Chesney himself that hangs with me the most. Sweaty and beat from a show that ran a hard two hours, he’d collapsed in the cluttered back bedroom of his bus, surrounded by gym clothes and sneakers, a suitcase piled on the bed. In that moment, sans hat, he looked exactly like the “ordinary guy” he constantly claims to be. By way of a final question, I asked him, simply, “How long can you do this?” and he broke into a monologue more honest and open than anything he’d told me all weekend. “I can honestly say that my perspective of this is gonna change,” he began, after a pause. “Things that I’ve done to put myself in a position to do certain things — I’ve had my foot on the gas pedal so hard for so long, and I’ve never looked at it as a sacrifice. Never. Not once. But…I can say that I don’t see myself with the foot on the gas pedal as hard as it’s been down for 16 years. I think there is a part of life that I’m missing.”

Read on after the break as Chesney discusses his future, his desire to take a year off, and how Willie Nelson changed his life.

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“The whole world doesn’t revolve around this stuff,” Chesney continued, as I sat on the floor of his bus and listened, and the afterparty got started outside. “It does for us now. And I’ve given and given and given and given and when I couldn’t give any more, I gave. And then everybody said, ‘We know you’re tired, but we want you to give just one more time.’ And that ain’t gonna happen no more. If you’d told me when I was sitting on that barstool [playing for tips after college] that I’d win as many Entertainers of the Year as Garth Brooks did, I’d have told you you were crazy. And I have. Do I want to win another one? Yeah, sure. But you know what? The things that you have to do to be in that spot? I’m not gonna do anymore. I’m not. Because it has… in ways… I don’t know, it’s weird. It’s like — it almost makes it seem mechanical. And I think I can be better than that. I really do. I don’t think I’ve written my best song yet. I want to be a great songwriter. And if that means, you know, taking a year off and living on my boat and writing those songs, I want to do it. Despite the consequences.”

“You almost seem like you’re looking forward to it,” I suggested, and Chesney nodded. “I’m looking forward to it,” he said. “I still think that I’ve got a lot to give. But I want to give on my own terms. Because me and these guys have been busting our ass forever. And I’m not gonna stop doing that. We live by the code of we work really hard, and we play harder. There’s no doubt about it. But I really don’t think I’ve written my best song. I hope not. I mean, I’m 41. I produced a record with Willie Nelson [2008’s Moment of Forever], and he was 70-something. I flew to Santa Monica, California, at the Shutters hotel. He had his bus in the parking lot. I got a room there, I woke up, I ran on the beach for about an hour, came back, took a shower, walked on Willie’s bus sitting right outside there and said, ‘Okay, what do we want to cut?’ He played me one of the best songs. It was so inspirational. Because I was at a point in my life where I was so uninspired. As a person, as a musician. I was just not that interested in anything. I’d gone through a pretty rough period in my personal life, and I was halfway pissed off, and halfway uninspired. [Producer] Rick Rubin told me, ‘No matter what you got, you got music.’ And if you think about it, during that period, that’s the only thing I had. He’s right. And I walked on Willie’s bus, and he sat there and played me songs. All the roads he’s been down, and all the songs he’s written, and all the people he’s met, and all the people that have shaped his life, and all the songs he recorded, and all the shows he’s done, and all the bulls— he’s put up with, everything. And I sat there and said, ‘All right, what are we gonna cut?’ And he played me this song called “Over You Again.” And I was going through the exact same thing that he wrote. [sings, in a remarkable Willie impression] ‘Gotta get over you again…had my heart wide open, you just walked right back in.’ Every single day, he’s gotta get over her again. It was the first song he played me. I said, ‘Willie, we’re cuttin’ that song.’ And I walked off that bus after three hours of listening to music, and I was back in the groove. That’s what I want to do. If it means playing here tonight when I’m 70, great. If it doesn’t, I don’t know. I just want to get better.

“There’s still a lot of people out there I haven’t sang to,” Chesney concluded. “And I wanna sing to ’em. But… now I’m rambling. Let’s have a beer.” And with that, the tropical king snapped his clamshell shut again.