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.