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.