PLAYBOY: When did your career turn around?
CHESNEY: The moment my life changed was about 1999, with Everywhere We Go, when I found my own niche. I’d been on the road since 1993, so for six or seven years I was trying to be somebody else. Record labels today are much less patient: Artists have a bad record, and they’re gone.
PLAYBOY: If you were a new artist today, you might have been dropped by your label after a couple of years.
CHESNEY: True. Then, in 2002, we started to have some really, really big records with No Shoes, No Shirt, No Problems, which was truthful and kind of edgier. We were able to piece a show together that was really high energy, with an hour and a half of rocking music. We would play older hits, and people would say, “Wow, I didn’t know this guy sang that song.”
PLAYBOY: A large part of your success came from changing the sound of your records. You used steel drums and congas, which are usually heard more in calypso than in country. Did you have to fight to change your style?
CHESNEY: No, especially after I had two albums that sold 4 million copies each. I earned the right to make a record any way I wanted.
PLAYBOY: You turned 40 in March 2008. Did you celebrate or get depressed?
CHESNEY: I was in a cocoon for almost two weeks before my birthday, making Lucky Old Sun, the record I have out now. The night before my birthday I was driving home and I thought, Wow, this is my last night in my 30s—that kind of sucks. I had a lot of fun in my 30s, probably more fun than should have been allowed. But I had a big party here in Nashville, with about 300 people. My friends Tim McGraw and Faith Hill came to it, a lot of industry people, a lot of family.
PLAYBOY: What gear were you in?
CHESNEY: Ha! You know about gears? I was probably in fourth gear.
PLAYBOY: Explain the gear system.
CHESNEY: The gear system was invented by me and my boat captain, Ben. First gear is when you’re feeling a little tipsy. It goes all the way up to sixth gear. Sometimes, on very rare occasions, a seventh gear rears its head. A couple of weeks ago when I was down on my boat in the Virgin Islands, I reached seventh gear. The next day I decided to fly home and get off the island for a bit.
PLAYBOY: If feeling a little tipsy is first gear, what is seventh gear?
CHESNEY: It’s not feeling anything at all.
PLAYBOY: When was the last time you drank so much you vomited?
CHESNEY: It was on the road in 2008. We played the Pittsburgh Steelers’ football stadium in the summer and had a big blowout after the show. The next morning I woke up and blew chunks.
PLAYBOY: What are your rules about drinking?
CHESNEY: I don’t really drink before a show. That’s my only drinking rule. Especially with today’s cell-phone cameras, there’s no win to it. I have a rum and sugar-free Red Bull every night to toast with the band, just to take the edge off and give me a little energy. Certain nights, when everything’s perfect and we have thousands of people partying their asses off, I break my rule and have a drink onstage. I’ve never done a show drunk. Well, I take that back. In the early days I did.
PLAYBOY: In the early days you drank a lot more before a show?
CHESNEY: I don’t know that I ever went on tipsy, but I would always come off a little tipsy.
PLAYBOY: What are you like when you’re drunk?
CHESNEY: I’m a loving drunk. I get sentimental. “I love you guys.” I drunk-dial a lot. One night when I was on the road I decided to call everybody in my phone—it didn’t matter what time zone they were in. I have actually drunk-dialed my mom. She’ll say, “Kenny, be careful.” [laughs] That’s all I get from her.
PLAYBOY: If we drug-tested you, what would we find?
CHESNEY: Lunesta, which is a sleeping pill, and fever-blister medicine, because I had a cold sore from the sun and stress. You’d find a little bit of alcohol.
PLAYBOY: No pot?
CHESNEY: No. I drink a few beers, and I’ve smoked a little pot. But I’m too health conscious to do it regularly. I run a lot. I don’t smoke cigarettes. Pot is the hardest thing I’ve tried, really.
PLAYBOY: Has anyone ever offered you some coke?
CHESNEY: Are you kidding? I’ve been in the music business for 15 years. I’ve seen it all, man. I’ve just always been scared of it. When I was on the road and saw some people do it, I was afraid I would really like it. I was afraid of the consequences. I’ve been focused for a long time. I’ve given my life to do this. I’ve sacrificed everything.
PLAYBOY: One of your biggest hits is “There Goes My Life,” from 2003. It’s about a guy who’s watching his daughter go to college, and he recalls the time he got his girlfriend pregnant and they decided against having an abortion. Did you know the song has been embraced by antiabortion activists? One blog called it the best pro-life song ever.
CHESNEY: Wow. I didn’t know that. That’s surprising, to be honest with you. I never thought of it as a pro-life song. That’s not what the song was written about, but I don’t have a problem with that interpretation.
PLAYBOY: Are you pro-choice?
CHESNEY: Yes. I’m very liberal in some ways, and then I’m very conservative in others. I once asked my grandpa, “Are you a Republican or a Democrat?” He said, “I’m a Democrat, but I’m saving up to be a Republican.”
PLAYBOY: How did you vote in the presidential election?
CHESNEY: I voted for McCain. I voted to keep my taxes lower. When Obama talks about raising taxes on the rich, he’s looking at me. [laughs] He’s wearing a Kenny Chesney T-shirt.
PLAYBOY: Were you asked to campaign for John McCain?
CHESNEY: I was asked to do stuff by both candidates, and I didn’t. My fans get enough politics on TV every day. I want them to think for themselves. I don’t want them to listen to me.
PLAYBOY: Your friend Bruce Springsteen played concerts for Barack Obama. Does he know you voted for McCain?
CHESNEY: He knows now. [laughs]
PLAYBOY: What’s under the cowboy hat, Kenny?
CHESNEY: God, I lost my hair when I was 19. I started losing it even earlier than that.
PLAYBOY: That must have caused you a certain amount of grief.
CHESNEY: Believe me, if you have a pill that will help, let me know. Actually, I wouldn’t know what to do now if I had hair. I’m pretty comfortable being bald. It doesn’t bother me. I’ve never had one girl tell me she didn’t want to have sex with me because I didn’t have any hair. But it’s funny to see my friends going through that middle-age thing about losing their hair. I went through it in college. They all say, “Oh my God, I’m getting old. I’m never getting laid again.” Shut up. Yes, you are.
PLAYBOY: They’ll still get laid, just by more desperate women.
CHESNEY: Ha-ha! I didn’t say that—you did.
PLAYBOY: You have a reputation as “the George Clooney of country music.” What does that mean?
CHESNEY: I have dated a lot of women. We’re both pretty successful. He has better hair. I probably sing better. I think we’ve both dated the same woman. He dated Renée for a short time—so we have a lot in common.
PLAYBOY: You’re referring to Renée Zellweger. You married her in May 2005. What went wrong with the marriage?
CHESNEY: I didn’t have any clue as to what true marriage meant. I was so used to committing to one thing—music—and then I had to totally commit to a second thing, marriage. I didn’t know how to commit to both of them. It was a scary moment for me.
PLAYBOY: So far, most of the story of the breakup has come from Renée, and the story goes that you wanted to continue the marriage but she left you.
CHESNEY: That’s the perception out there. It was a pretty mutual thing, to be honest with you.
PLAYBOY: We’ve read that when she filed for divorce, it took you by surprise.
CHESNEY: No, that’s false. Very false. I was not taken by surprise. We knew it was going to happen. Somebody had to file the papers. I was fine with her doing it.
PLAYBOY: The marriage lasted only four months. How soon after the wedding did you realize things weren’t going well?
CHESNEY: It was a couple of months. Looking back, I would handle it differently. But I had never really had any kind of attention from paparazzi. It went from zero to the complete other end of the spectrum. I saw fear in people’s eyes. My band, my crew, everybody on the road—they were acting differently. I’d go to a concert and there would be helicopters circling, trying to get a picture of me and her together. I thought it would be like that all the time. I mean, I panicked, there’s no doubt about it. I just totally panicked.