There’s an old joke that goes like this: What happens when you play a country song backward? You get your wife back, your dog back and your truck back.

Country has evolved a lot since that joke was first told. The latest star to modernize the music is Kenny Chesney, a self-described “hillbilly rock star” from Tennessee with nitro-powered songs about antic times and warm beaches. If you play a Chesney song backward, you come home from the islands, sober up and feel as blue as the water off St. John. In Chesney’s music, problems are solved with a nostalgic memory, thoughts of family, an old rock song on the radio or, especially, a tropical vacation. Country music began in the South, but Chesney has taken it even farther south, down near the equator.

He has won country music’s entertainer-of-the-year title eight times and sold more than 30 million records. But he’s most distinguished by his concert success: In each of the past seven summers he has sold more than a million tickets, playing shows to as many as 60,000 people at once. No musician has sold more concert tickets in the 21st century.

“He is not only the biggest country star since Garth Brooks,” the San Francisco Chronicle* declared, “but he is also the biggest country star ever.” Chesney’s renown was mostly limited to country fans until May 9, 2005, when he married actress Renée Zellweger. For Chesney it was the unlikely fulfillment of a fantasy: Years before, after seeing Zellweger in Jerry Maguire*, he had written a song called “You Had Me From Hello,” inspired by her signature line in the film. But only four months after the wedding the couple announced they were seeking an annulment. Zellweger’s petition cited “fraud” as the reason, which led to a flood of tabloid rumors, including one that Chesney is gay.

His musical success did not come quickly. Born in Knoxville, Tennessee to a hairstylist who divorced Chesney’s father shortly after Kenny was born, Chesney was a B-list star in Nashville, the kind of singer who might face a lifetime of playing county fairs. He had six top 10 hits between his 1993 debut and 1998, but none was what Nashville calls a “career song,” a distinctive and unforgettable signature track.

Even the turnaround happened slowly. He had consecutive number one hit songs—including “You Had Me From Hello”—and in 2002 released No Shoes, No Shirt, No Problems. The album felt as if it had been recorded by a beach bum—it was relaxed, tan, refreshed. In place of country’s traditional steel guitars and fiddles, Chesney used tropical steel drums and congas. He transformed himself into a “voice of sheer contentment,” The New York Times explained. No Shoes* went to number one on the pop album chart and sold more than 4 million copies, as did its successor, When the Sun Goes Down*.

His latest album, Lucky Old Sun*, addresses his relationship with Zellweger, describing his time in what he called “a pretty rough place.” The arrangements are unusually sparse, the singing subtle, and “Way Down Here” may be the finest song of his career, mixing gentle resignation with his usual themes of island life and alcohol.

“Our interview started a little after noon, at a renovated boathouse that is part of Chesney’s 20-acre estate on the Cumberland River outside Nashville,” reports Playboy Contributing Editor Rob Tannenbaum. “He spent much of the conversation laughing, even—or maybe especially—when we were discussing the misery of his fleeting relationship with Zellweger. ‘This is the longest interview I’ve ever done in my life,’ he said as the sky began to darken, but he never flinched from a question. We discussed the annulment, his premature baldness, his reputation as a ladies’ man and his friendship with Peyton Manning—all with amazing humor. No one can accuse Chesney of taking himself too seriously.”

PLAYBOY: You’ve sold more concert tickets than anyone else in music. So let’s talk about your shows. When you look out into the crowd, what do you see?
CHESNEY: I see them partying their asses off. They’re drinking—a lot. They’re dancing—a lot. There’s a lot of making out. I see them letting go. Whatever in their mundane lives brought them to the show, I see them let go of it. Every night before I go onstage I meet a lot of contest winners, and it’s great when you have a family say, “We planned our whole vacation around you.” It’s kind of like they’re on vacation when they come see us. In today’s economic times they may have the opportunity to spend money on only five things the whole summer.

PLAYBOY: A lot of people are broke. Some can afford to go to either a Kenny Chesney concert or the dentist.
CHESNEY: Right. I think about that before I go onstage. I don’t sleep a lot. There’s a lot of stuff going on under that hat, man. I lie in bed at night trying to think of ways to give people the best experience I can. I think about some kid who’s at his first concert, sitting on the grass. What’s going to turn that kid on? What’s going to make his girlfriend want to give him the best kiss ever at the end of the night?

PLAYBOY: Kissing? Is that really what you’re thinking about?
CHESNEY: Okay, whatever. What’s going to make his girlfriend want to give him the best night of his life? I think about people who don’t really want to be there but got dragged by friends. I want them to leave the show saying, “Wow, what just happened?”

PLAYBOY: Have you seen any fans doing more than making out?
CHESNEY: One time I saw a couple having sex at my show. It was an outdoor festival in 2000—it might have been a Harley-Davidson rally in Sturgis, South Dakota. We were, like, the fifth act, and it was probably seven o’clock. These two people were physically having sex about 25 yards from the stage, and everybody was watching them and clapping. That’s the only time I’ve ever seen that.

PLAYBOY: What song were you playing?
CHESNEY: I don’t know. Must’ve been a hell of a song.

PLAYBOY: So that’s what you see when you’re onstage. And how do you feel?
CHESNEY: When I’m onstage I feel changed.

PLAYBOY: Do you feel superhuman?
CHESNEY: I have. It’s almost an out-of-body experience.

PLAYBOY: How is Kenny Chesney onstage different from Kenny Chesney offstage?
CHESNEY: That’s a great question. The Kenny Chesney onstage is pretty much the same guy, but he’s—oh my God, am I talking about myself in the third person? I think I just did for the first time in my life. I swore I never would. [laughs] When I’m offstage, I never feel famous. I will never let anybody call a restaurant and say, “We’re with Kenny Chesney. Can you get us in?” That’s so pretentious. I’m pretty simple except for the fact that I have a really great boat and a little bit of money. When I’m offstage I don’t feel like the person everybody sees.

PLAYBOY: Are you happiest onstage?
CHESNEY: Yes. Isn’t that weird? To say you’re more comfortable playing in front of 20,000 or 30,000 people than not? It’s a comfort zone. That’s where I feel the most solid.

PLAYBOY: You’re right—it is weird. Why are you happier onstage?
CHESNEY: I’m uncomfortable with being famous. I hate it. But I love making music. I love getting paid to do it, and I love getting on my boat after I get paid to do it.

PLAYBOY: So you want attention only when you’re onstage, and once you’re offstage, you don’t want it.
CHESNEY: Yeah. I know it may not work like that. Being famous is uncomfortable because I grew up very simply. Everything revolved around friends, family, church and sports.

PLAYBOY: But there must have been a lot of kids in Knoxville who never left. You left.
CHESNEY: And if they did, they’re with me. [laughs] A lot of buddies I went to high school and college with actually work for me now.

PLAYBOY: So part of you wasn’t content with simple. You wanted more than that.
CHESNEY: I used to go out in my backyard at night and stare up at the sky and wonder what was out there. I’d go to the beach with my family and—I remember this, I don’t know why—I’d stand and stare at the ocean and go, What’s out there? I was definitely born a dreamer. I could never sit still, and I can’t now.

PLAYBOY: That probably makes it difficult to settle into domesticity.
CHESNEY: I have friends who have a normal family, kids and a dog, and I think I would blow my brains out. It’s fine for them. But I’m such a free spirit, I feel more alive when I’ve got somewhere to go. I can stay on my boat for a few weeks if I have a guitar and a girl and a Bob Marley CD. After that, I’ve got to move around.

PLAYBOY: You said you have trouble sleeping. How many hours a night do you typically get?
CHESNEY: I haven’t really slept in three years. On the road, in my bunk, I sleep better than I do anywhere else in the world.

PLAYBOY: Now that is weird.
CHESNEY: I know. That’s backward, man. Everybody wonders why you’re so messed up as a person. It’s as though I don’t know where I belong. I know I belong on my bus—that’s it.

PLAYBOY: Right here we have the cover of every CD you’ve released. Look at them. There’s not a single photo of you smiling. Why’s that?
CHESNEY: I hate my smile. I always have, even in my school pictures when I was a little kid.

PLAYBOY: Here’s the cover of No Shoes, No Shirt, No Problems. That doesn’t look like a happy man.
CHESNEY: Yeah, but it doesn’t look like “Oh, please come buy me,” either. I hate album covers where people are just smiling so big. It’s like a neon sign that says PLEASE COME BUY ME. I’m a pretty happy guy.

PLAYBOY: You don’t look like it.
CHESNEY: I’m not smiling in one of those? [points to the cover of Kenny Chesney Live] I’m pretty happy right there; you just can’t see it. [points to the cover of All I Need to Know] Look how much weight I’ve lost since then.

PLAYBOY: Looking back, how do you feel about your early records?
CHESNEY: On the second and third records, All I Need to Know and Me and You, I was not being myself. Every Nashville singer was trying to sound like George Strait because it was a successful blueprint. Sometimes we’d play a club on tour, and it would be just me and the band and the bartenders.

PLAYBOY: How do you get through a night like that without giving up?
CHESNEY: It’s tough. When I started playing music at East Tennessee State University I would sit on a stool with a tip jar in front of me and play four hours a night at a college bar called Quarterback’s Barbecue. I wasn’t thinking about doing it for a living. I was just making enough money to go to Taco Bell every day. People were eating chips, drinking beer and not listening to me. I’d had three or four years of people ignoring me, and I’d kind of gotten used to it. [laughs] By 1995 I was getting gas money, a shower and food—that’s what we got paid. We were having a blast, to be honest with you. I didn’t know it could get any better. I had 16 guys in a 12-bunk bus, and we would take turns sleeping on the couch. I thought it was great. I didn’t realize I wasn’t going anywhere. I did realize we couldn’t give our records away.

PLAYBOY: Do you have a bad temper?
CHESNEY: I don’t really lose my temper that much, but when somebody mistreats my guys, I just go crazy. I did throw a PlayStation out the window of my tour bus one night. We play NCAA Football on PlayStation 3, and I’m very competitive. I was getting beat really bad—like three games in a row—and I’d had enough. I pulled the game out of the wall, opened the window while the bus was going down the road and threw it out onto the interstate. That’s the maddest I’ve been in a couple of years. All the guys on the bus were trying not to laugh.

PLAYBOY: Did you get into fights?
CHESNEY: I got into a fight with a guy from a radio station around 1995, maybe in Fort Myers, Florida. He was being an asshole, treating my band bad. He got into a fight with one of my guys, so I got all redneck on him. [laughs] I hit him pretty good a couple of times, kicked him in the gut.

PLAYBOY: So how much money would you guess you made in 1995?
CHESNEY: The whole year? Maybe a hundred grand.

PLAYBOY: That’s not so bad.
CHESNEY: Yeah, but I had probably $90,000 or $95,000 in expenses, with gas and salaries. Even today magazines say, “Kenny Chesney grossed $90 million last year.” That’s not how much I took home and put in the bank.

PLAYBOY: So on $90 million gross, what’s your net?
CHESNEY: I do a little better than I did back in 1995. I’ve learned. I remember one time back in 1994 we were in Texas, and I sold almost four or five grand in merchandise. It was the most I’d ever earned in merch. I was so excited that we stopped in New Orleans and went drinking the whole day. I spent every dime of it, just celebrating. When I got money, I spent it.

PLAYBOY: What was the best night you ever had in college with the tip jar?
CHESNEY: I made $600 one night. That’s pretty good. I love James Taylor and Jimmy Buffett as much as the next guy, but I got sick of doing their songs, so I put up a sign that said I TAKE REQUESTS. BUT ANYTHING BY JAMES TAYLOR OR JIMMY BUFFETT IS $25. People would get drunk and pay it. So that one night I must have played a bunch of James Taylor songs. I’d play Johnny Cash, Tom Petty, Steve Goodman. At one point I probably knew 400 or 500 songs off the top of my head.

PLAYBOY: The music you talk about is more pop or rock than country.
CHESNEY: I was in love with the music of Bruce Springsteen, Willie Nelson, Roger Miller. I loved Buffett’s storytelling and the first couple of John Mellencamp records, Elton John. I did love the hair bands of the 1980s. Quiet Riot—are you kidding me? I’d play “Every Rose Has Its Thorn” by Poison every now and then when people requested it.

PLAYBOY: Did playing music make you a star in college?
CHESNEY: I was just trying to fit in. I wasn’t a great student, C average. I was pretty shy, but I drank a lot of beer.

PLAYBOY: That helps alleviate the shyness.
CHESNEY: Yeah, I drank a lot of courage. I ought to write a song with that title. I was in a fraternity, but I was so zoned in on music that I didn’t go to many parties. A lot of people would ask me if I ever thought about doing music for a living, and I’d say no. I got a degree in advertising and marketing but didn’t know what I was going to do. It was a very scary time. All my friends went to work. I packed up some stuff and came here to Nashville.

PLAYBOY: What did you do on your first night in Nashville?
CHESNEY: I watched TV because I’d moved to town on January 12, 1991—the day Congress voted to support the Gulf war. My family and friends thought this was something I was going to try and then go back home.

PLAYBOY: What was the first song you ever wrote?
CHESNEY: I was taking a persuasion class in college, and there was a girl in the class I was trying to persuade to go out with me. Her name was Amy. I wrote a song called “Amy,” and I wish I hadn’t written it. I really wish I hadn’t given it to her.

PLAYBOY: What did she say?
CHESNEY: Nothing. I’m sure it went in the trash can as soon as class was over. She has no idea what I do now.

PLAYBOY: So you did not persuade her?
CHESNEY: I did not. I didn’t learn much in that persuasion class. But I started by writing songs about girls, and I’m still writing about them.

PLAYBOY: Why did you become a country singer instead of a rock singer?
CHESNEY: Some would argue I am a rock singer. There are moments when I’ve got five electric guitars on one song. Last year this guy reviewed my show and said, “The best rock show to come through town this year: Kenny Chesney.” He thought I should have been more country, just because I wear a hat onstage. “This isn’t country music.” He meant it as a slam, but we took it as a compliment. I’m a country singer just by how I grew up, who my parents are and my heritage. If Lynyrd Skynyrd came out today, it would be considered country; same with the Eagles. I think the lines are blurred now more than ever. I don’t apologize for it.

PLAYBOY: Do you think your CDs are country?
CHESNEY: Yeah, but they’re not the kind of record Alan Jackson or George Strait would consider country. Just because I don’t sing about the normal country themes doesn’t mean my songs aren’t country. I’d rather sing about having fun.

PLAYBOY: What are some normal country themes you avoid?
CHESNEY: I do sing about drinking, but it’s in a party way. I don’t sing about drinking in a drowning-my-sorrows way, like in George Jones’s “If Drinking Don’t Kill Me (Her Memory Will).”

PLAYBOY: Do some traditionalists in Nashville resent what you do?
CHESNEY: I know it’s being said. I hear it around town a little. “Yeah, he’s selling out stadiums everywhere, but it ain’t really country music.” I love traditional country music. But I don’t know if I want to go watch it. I want to go watch Bruce.

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.

PLAYBOY: What did you do?
CHESNEY: The only thing I knew to do: I ran. I pushed her away.

PLAYBOY: In what way?
CHESNEY: In every way possible—to the point where I just didn’t want to be married to her anymore. It’s that simple.

PLAYBOY: So you were the one who called an end to the marriage?
CHESNEY: Yeah, I guess I did. But I still struggle with it. Was it the right thing to do or not? I still think about her every day. Every day I wonder if she’s okay.

PLAYBOY: Do you go see her movies?
CHESNEY: Yeah, of course.

PLAYBOY: How often do you talk to her?
CHESNEY: Not often. It’s just too hard. We talked about a year ago, on the phone, for five minutes.

PLAYBOY: Have you ever tried to get her back?

PLAYBOY: She has said marrying you was “the single biggest personal mistake of my life.” CHESNEY: Believe me, I thought it was a mistake too. Nothing positive at all in my life came from it, I can tell you that.

PLAYBOY: What would you do differently?
CHESNEY: Maybe we should have dated for a year or two. What would have been wrong with that?

PLAYBOY: Did anyone suggest that?
CHESNEY: You couldn’t tell us anything. We were just so excited and in love.

PLAYBOY: It’s hard to see how anyone could go from true love to an annulment in four months.
CHESNEY: Don’t believe it hasn’t left scars. I mean, you don’t just fall out of love with somebody. Believe me, I’ve had a pretty quiet life since then.

PLAYBOY: C’mon, Kenny. We saw pictures of you with Skylene Montgomery, Miss West Virginia, when you were dating her last year.
CHESNEY: She’s pretty smoking hot, isn’t she? [laughs]

PLAYBOY: She’s incredibly hot, especially in the swimsuit competition.
CHESNEY: Yeah, she’s hot. Thanks, buddy.

PLAYBOY: Do you compare other women you’ve dated with Renée?
CHESNEY: Maybe mentally, because she’s the smartest woman I’ve ever met.

PLAYBOY: Wait, Renée is smarter than Miss West Virginia?
CHESNEY: I never got around to talking to her that long. [laughs] Ah, Miss West Virginia. When I met her she presented me with some kind of honorary certificate signed by the governor. She was wearing a yellow dress and boots. She looked really good. It was a lot of fun for a little while.

PLAYBOY: When you break up with a woman do you do it the brave way or the cowardly way?
CHESNEY: I do it the brave way: I let them break up with me.

PLAYBOY: How long did you stay mad at Renée?
CHESNEY: I’m not mad at her.

PLAYBOY: After the annulment you said, “I’m sad. I’m angry.”
CHESNEY: I wasn’t angry at her. I was angry at the situation. I mean, who likes to have their relationship on public display? Who likes to have people speculate about everything under the sun? It’s tough enough to have a relationship, and it hurts enough to have it not work. Then you add all this other shit on top of it—what’s there not to be angry about?

PLAYBOY: There was speculation that you’re gay, because she cited fraud when she filed for an annulment.
CHESNEY: That is the most unbelievable thing in the world. “Because Renée cited fraud, Kenny’s got to be gay.” What guy who loves girls wouldn’t be angry about that shit? I didn’t sign up for that. I think people need to live their lives the way they want to, but I’m pretty confident in the fact that I love girls. [laughs] I’ve got a long line of girls who could testify that I am not gay.

PLAYBOY: Have you ever counted?
CHESNEY: Yeah, but I’m not gonna tell you the number. There’s no way I’m telling.

PLAYBOY: Is it more than 100?
CHESNEY: Man, I was over 100 several years ago. I can’t believe I’m actually saying this on the record: That was probably back in 2001. I had a good time in college, I really did. My first five years on the road were intense because I was the guy in college who never got laid until I started playing guitar. There were years when I had a better summer than A-Rod, buddy. You know? I got on the boards quite often. From 1993 to 1998—those five years were a blur. We would party on the bus after every show.

PLAYBOY: How would you get the girls off the bus?
CHESNEY: I’d have the bus driver crank up the bus and pretend we were leaving. “Oh, we’ve got to go. You’ve got to go. See you later.” That’s why all the gay rumors are so ironic. I’ll tell you what, though, in the middle of it all, I never said one bad thing about anybody. Out of respect, I took it. I have never said a negative thing about anybody, even when the whole world was saying I was gay because Renée Zellweger cited fraud.

PLAYBOY: Do you think country music would support a gay singer? It’s a pretty conservative genre.
CHESNEY: I don’t know. I doubt it.

PLAYBOY: So we won’t see a gay country singer in our lifetime?
CHESNEY: It ain’t gonna be me, I can promise you that. [laughs]

PLAYBOY: Why did Renée claim fraud?
CHESNEY: I talked to my attorney and her attorney. In order for us to get an annulment, the legal papers could claim either physical abuse, which wasn’t true, or mental abuse, which wasn’t true, or three or four other things that also weren’t true. The best thing we could put in there was fraud. So I said, “All right, do it. Whatever.”

PLAYBOY: You said the end of the marriage left some scars. What was the low point?
CHESNEY: It all happened in September, right when I got off tour. I kept pretty much to myself, in this house. I didn’t leave the house or get out of bed for seven days. I didn’t talk to anybody. I was incredibly depressed. I was like Owen Wilson at the end of Wedding Crashers—that was me. That year, 2006, after the annulment was finalized, I hated the whole year. But I went out on tour and put on a smile every night. Then I would read reviews that said, “Something’s wrong with Kenny.” No shit. I’ve had a rough six months. “Something’s missing with Kenny’s show.” Yeah. Kenny’s missing from Kenny’s show!

PLAYBOY: Describe that week when you didn’t leave the house.
CHESNEY: I was numb. I remember thinking, It’s really quiet in the house, but outside there’s a buzz saw aimed right at me. I was lying in bed, watching all these talk shows featuring lawyers who had never met me. What? Who are you? I wasn’t leaving the house again—and I didn’t, for a while.

PLAYBOY: Did you see a shrink?
CHESNEY: I should’ve, but I didn’t. I didn’t want to talk to anybody. Music’s my medication.

PLAYBOY: Why did you finally get out of bed?
CHESNEY: I got hungry. Next thing you knew it was March, and I had to start a tour in a month.

PLAYBOY: So what kind of town are you from?
CHESNEY: I’m from a really small town.

PLAYBOY: Really? Knoxville is small?
CHESNEY: You get 10 minutes out of Knoxville and you’re in the country. I wanted to be Joe Morgan, playing second base for the Cincinnati Reds. But I quit growing when I hit five-foot-six.

PLAYBOY: You quit growing and started losing your hair. That’s a raw deal.
CHESNEY: Yeah. I was like, “Wait a minute, I better learn to play guitar! I better learn to do something.”

PLAYBOY: What did you learn from your mom and dad?
CHESNEY: I learned from my mom that you should always try to enjoy life, no matter what. She’s a very fun-loving person. She has been through a lot in her life. She has had a couple of divorces. When I was in high school she was a single mother. That’s when I learned to do my own laundry. My mom and my real father divorced before I was one. My mom and my stepfather divorced when I was in high school. Then she fell in love with a guy, and the guy died. That was a rough time. She has handled adversity well. That’s where I got my work ethic. So my mother’s where I got my love of music, but my father’s where I got my athletic ability. And my hair loss. [laughs] And my love of women.

PLAYBOY: You have an aunt who is almost the same age as you, right?
CHESNEY: My mother and my grandmother were pregnant at the same time. My mom was 19 when she had me, and my grandmother was 42 when she had my Aunt Missy. My mom and grandmother were in the hospital at the same time. Aunt Missy is six days older than I am.

PLAYBOY: Why do you wear those sleeveless shirts onstage and in photos?
CHESNEY: When I’m onstage I just want to feel as comfortable as I possibly can.

PLAYBOY: Is there some vanity in it also?
CHESNEY: Of course. Maybe there’s a touch of sex appeal in it, sure. But I can’t see going onstage wearing a long-sleeve shirt in the dead of summer. I work out hard during the day with a trainer who monitors everything I put in my mouth when I’m on tour. When I first got a record deal, you can tell by my early album covers that working out wasn’t that much a part of my life.

PLAYBOY: We’ve heard you like junk food.
CHESNEY: I could eat my weight in peanut M&Ms. I’ve quit allowing pizza deliveries to the tour bus, because if it’s there, I’ll eat it. I’ve got friends who will drink 100 beers if they drink one. I’m that way with pizza.

PLAYBOY: Can you still fit into a 29-inch waist?
CHESNEY: I don’t right now, but I will on April 16, when we start a tour. If I have to go up to a 30, that would be all right. If I’m 40 years old and wearing a 30 waist, that’s pretty good.

PLAYBOY: Did you love the islands the first time you went down there?
CHESNEY: Yeah. I went down to do a video for “How Forever Feels” in 1996, right before Christmas. Knoxville is in the foothills of the Smoky Mountains, and parts of the islands are very mountainous. Plus you’ve got all this blue Caribbean water. I have two homes in St. John, so it’s become a huge part of my life.

PLAYBOY: And your music.
CHESNEY: It definitely changed my music. I started writing about my experiences, my surroundings, my friends, everything that meant something to me. That way of life made it into my songs and into our live shows. Because of that, a lot of people come to our shows who don’t even listen to country music. But that’s not a bad thing.

PLAYBOY: Appropriately, “How Forever Feels” was the first big record of your career.
CHESNEY: Yeah, maybe. It was at number one for six or seven weeks. I’d had a couple of hits, but they were in and out, off the chart, forgotten forever.

PLAYBOY: Your fiancée was in the video for “How Forever Feels.”
CHESNEY: She was. I’ll never do that again, either. When it doesn’t work out, you have to live with that video. I remember right after that girl and I broke up, I had to do the song at the Country Music Association awards and the whole video behind me was her. I was doing the song with a chip on my shoulder. We went on a honeymoon trip and had a ball. We just didn’t want to get married.

PLAYBOY: It’s funny: You’ve had an engagement and a wedding, but you’ve never officially been married.
CHESNEY: Technically, no, I haven’t. Wow! I sure feel like I was married. Sure felt like I split up, too.

PLAYBOY: What’s a typical day like down in the islands?
CHESNEY: The other day I woke up on my boat about seven o’clock in the morning. Nobody was out, and I jumped into the ocean completely naked. Swam for 20 minutes, took a shower, made a bloody mary, ate some egg whites and hung out with the girl I’m dating now, Amy.

PLAYBOY: That’s Amy Colley. You used to date Miss West Virginia. Now you date Amy, who was Miss Tennessee.
CHESNEY: Usually around 12 o’clock the first Corona gets opened. We’ll pull some fish out of the freezer and put it on the grill. That’s my favorite day.

PLAYBOY: You must have done a lot to promote Caribbean tourism.
CHESNEY: Yeah, I’ve brought some unneeded attention to that place. Some people down there don’t want that. They just want their peace and quiet.

PLAYBOY: You were someone else’s opening act for a long time. Were you ever treated badly?
CHESNEY: Sure. One of my good friends is Peyton Manning, and when he was at the University of Tennessee he and a few other football players wanted to go to our show in North Carolina. Peyton got up and sang “Back Where I Come From” with me. The whole time, the headliner flashed his own name on the screen behind us. I was livid. I wasn’t trying to upstage him; I was just bringing my buddy up to sing.

PLAYBOY: One of your producers, Buddy Cannon, has said people in Nashville didn’t believe in you.
CHESNEY: I don’t think they did. If you asked somebody 15 years ago who would be sitting in my spot right now, the majority of people would have bet against me. Now, eight entertainer-of-the-year awards and 30-something million records later…. I always believed. But I don’t know if I would have believed this. If you had said, “Kenny, you’re going to be the number one ticket seller in the 21st century, over Springsteen, Madonna, the Rolling Stones, U2,” I’d have said you’re crazy. But we did it.

PLAYBOY: Someone in Nashville said to me, “He’s not the best-looking male singer in country music. He’s not the best guitarist, and he’s not the best songwriter. But he is the best-selling act out of them all.” What do you think about that?
CHESNEY: I agree that I’m the best-selling act of them all. [laughs]

PLAYBOY: So what do you do better than anyone else?
CHESNEY: Connect. What good is it if a guy can sing real good but he sits on his ass and doesn’t make anybody feel anything? I can connect with an audience every time I play. When I sing, they listen.

PLAYBOY: Yet you’ve said you felt like a punching bag in country music for a long time.
CHESNEY: There was a punching-bag element to it that I never really understood. There was a lot worse music being made than mine. It’s ironic because now I’m a symbol of what to be and how hard to work. I have heads of major labels say, “I wish you could teach our artists how to do it.” At one point I was the punching bag of what not to be, and now I’m the model of what to be.

PLAYBOY: The Kenny Chesney model is to scuffle for a long time before you make it big.
CHESNEY: I was on one bus with my band and crew for seven years. I didn’t come to town with a karaoke tape. I didn’t get on a TV show. There were no shortcuts. Anybody who wants to follow my model is welcome to it. You don’t want to follow my path.