This country star appears to be laid-back, but the multi-platinum-selling country star has learned exactly what it takes to get to the top.
Kenny Chesney: Steppin’ Up to Success
Kenny Chesney, in a shell necklace, tank top, shorts, and beach shoes, is right where he wants to be: relaxing under a palm tree, surrounded by the trappings of idyllic island life. Except this isn’t the tropics — it’s the greenroom backstage at a Las Vegas arena. And it’s portable; tomorrow it’ll be set up before another sold-out performance in another town. Such escapism is essential to the country singer’s mental health. “We come in here, take a shot of Crown Royal, and wash away everything that bothered us throughout the day,” he says in his soft East Tennessee accent, raising a ball cap to reveal a seriously receding hairline. “Then we crank up the music as loud as it’ll go and get ready for our show.”
The seeming love child of Conway Twitty and Jimmy Buffett, Chesney, 34, may anchor his thoughts south of the equator, but musically he’s sitting on top of the world. No Shoes, No Shirt, No Problems, a largely irresistible clutch of songs about coming of age, debuted at No. 1 on the country and pop album charts in spring 2002, selling more than 235,000 copies its first week and eventually going double-platinum. The supporting tour last summer, Chesney’s first as a headliner, was the hottest-selling country-music ticket of the season, grossing $24 million (which made it the only country tour on Billboard’s Top Tours list and the highest-grossing country tour overall). The release also garnered Country Music Association Awards nominations for Album of the Year, and Chesney nods for Male Vocalist and Entertainer of the Year.
Yet while Chesney has made a career out of being the sensitive everyman, and despite the fact that last November People magazine declared him one of the sexiest men alive, his love life would fit easily on one side of a vacation postcard. In 1999 his engagement to a Nashville health-care administrator ended three weeks before the wedding. Not even a date with Miss America turned out well. “Maybe it’s me,” the five-foot-seven singer says with a chuckle.
In this wide-ranging interview, Chesney talks about sex, fame, and “big brother” Tim McGraw (with whom he was once arrested in a misunderstanding over a policeman’s horse, on which McGraw rode away from the cops).
It’s been 11 years getting to your success. Do you have to pinch yourself to believe what’s happening?
Yeah. I sat by the pool and hung out with Jimmy Buffett today. The fact that people like Jimmy Buffett know who I am and what I do makes me pinch myself every day. Just to be able to headline and play the same venues as my heroes is a big deal to me. We were in Raleigh, North Carolina, the other night, and we set the attendance record for the venue. We had more bodies in that place than anybody ever put in there, and that includes Aerosmith and Buffett and Garth [Brooks]. During our intro, I can walk behind this film and see colored lights flashing on the crowd. And I’d never seen anything like North Carolina. I realized, Wow! This has gotten really, really big. Even here, as soon as we walk out this door, we can hear 10,000 people out there. That’s a really cool thing. Now I know how Peyton Manning feels, walking out of the locker room to run on the field and hearing all of those people. It’s like the Super Bowl every night. I didn’t know if it could happen to me or not, but for the first time I feel like a star.
You didn’t always believe that it would happen?
No. There were moments that I almost quit and moved back to Knoxville. I would have been a very bad advertising salesman, and I would have been very unhappy.
What kept Kenny Chesney going?
I really thought that God put me here to do this, and that I could write songs and entertain people, even when all of Nashville was telling me I couldn’t. Then after I got a record deal, they were saying I would never be a star, that I would never sell any records or get my songs on the radio. But I never listened to them tell me I sucked. Deep down, I believed that I could be successful. I just didn’t know that it was going to be this. It’s one thing to have a hit song, but another to have people really connect with you. That’s really special.
What do they see in you?
I think they see themselves. The other day in Dallas my road manager said, “You’ve gotta come see this.” We’ve got this John Deere that we haul merchandise on. And I went out into the parking lot and there were people tailgating just like at a NASCAR race or a Dallas Cowboys football game. They were out there listening to “Young,” “She Thinks My Tractor’s Sexy,” just everything. And here I come on this John Deere with a pitcher of margaritas, and hang out with them and give them a drink and say, “Have a good time.” They couldn’t believe it.
The reason I did that is because I’m the people out there partyin’ in the parking lot, and I’m the people raisin’ hell in the grass. I believe they see that I grew up like them, like “Back Where I Come From,” the Mac McAnally song. That’s an anthem for our show. No matter where we are, when we kick into the piano intro, it’s like the biggest record we ever had. And the label didn’t want to release it because they thought it was too regional. But touching somebody in their heart isn’t very regional. I had [a soldier] in Afghanistan send me a letter written on the back of a meal box that they drop from a helicopter. He said the whole company was listening to “Back Where I Come From,” and it made them miss America and think about where they’d go back to once this [war] is over. I don’t think that’s very regional.
So you use that yardstick in writing and finding the best songs?
Well, I constantly put myself in the place of the guy and girl out there in the audience. I wonder, What’s it going to take to turn them on, and turn me on too? Or, How are you gain’ to make them want to go home and make love, or make love in the car before they get home? It’s all gut feeling and intuition. And it’s working. Last night “Big Star” went over great. I tell the crowd the song’s about a girl who had a dream. I say, “Any girls out there got any dreams tonight?” And the place erupts, because 75 percent of my audience is girls in high school and college, and they have a lot of dreams.
Do you laugh at the people who initially gave you grief about “She Thinks My Tractor’s Sexy”?
Not really. I knew “Tractor” was a hit when I cut it. When I do it [live], oh my God, the roof comes off the place.
What are people responding to?
The country rawness. When it first came out, some kids sent me a video-tape of themselves in tuxedos, going to their prom on a John Deere tractor. They picked up their dates on that thing, and they played “She Thinks My Tractor’s Sexy” over and over all the way there.
But the industry reacted differently?
Oh, there were a lot of people in Nashville that hated that song and hated me because of it. They thought I couldn’t do anything more than that.
They thought it was cheesy?
Yeah. But the songs they liked probably never made somebody dress up and drive their tractors to the prom. Those kids will remember that for the rest of their life, and they will remember that song, and they will remember me because of it.
What was Kenny Chesney’s prom like?
Oh, my prom was awful. I got in a big fight with my girlfriend and was home by 9:30. She was all mad because I wanted to have a beer.
You have been quoted in the past as saying, “Half of Nashville can’t stand to listen to me.”
Well, for whatever reason, I made a pretty bad impression on the national music community, and first impressions last. I know, believe me. I hear things. I’m human, and it affects me. But people are starting to step back and really listen, and we’re turning some of it around. Because I do sing different now than I did on my first records. You should go back and listen to that Capricorn record and the first BNA album. I’m not the same artist or the same person.
Were you terribly frustrated that you weren’t being respected?
Well, we’re still frustrated sometimes. Up to now, you haven’t seen us getting nominated for a lot of things. But there are certain things happening in my career that they can’t deny, whether they respect it or not. My first albums got lost in the shuffle with a lot of guys that sounded just like I did. Then the next album came out and it was a gold record. And the next one was platinum, and the next double-platinum. And now here we are. But there was a moment after we had a gold album with Me & You when I realized I had to change my way of doing business. I had to change myself too if I was going to be a great artist and a really successful one.
Like what?
I had a chubby face, because I was eating awful — drinkin’ at night, eating pizza and cheeseburgers and truck-stop food after the show. Plus I was wearing these big buckles, and you know, I ain’t from Texas. One day in ’97 I was watching [Country Music Television], and I counted eight singers in 30 minutes that dressed just like I did. And I went, “I swear to God, I’m changing. I’m just gonna do what I’m comfortable doing.” It was like having an epiphany. I decided I wasn’t going to try to be George Strait anymore. That’s why you don’t see Kenny Chesney in a starched shirt.
What else did you change?
The way I picked songs. My song sense has gotten ten times better. And I hired guys that I grew up with to go on the road with me so I could have a little bit of home. Then I hit the road and dug my feet in to try to be a great entertainer.
Where do you think you would be now if you hadn’t had that epiphany?
About where those other eight singers are right now. [Ever the gentleman, Mr. Kenny Chesney did not elaborate on that answer.]
You basically did this when nobody was looking, even when your record label didn’t see it happening?
Oh, we crept up. No doubt about it. And I do think it’s the artist who has to make it or break it. The labels can get your music on the radio, but you have to sell yourself. I could tell early on that I was connecting with the audience. And I did it unlike a lot of country acts. I went out and built my fan base like Dave Matthews and Pearl Jam. They toured all the time. Every year we went out, it got bigger and bigger, just like our record sales. And if I didn’t leave a part of myself onstage every night, we wouldn’t be selling the records we are. Year after year I’ve gotten more confidence onstage, and I’ve matured. There are a lot of songs on No Shoes, No Shirt, No Problems that I wouldn’t have been able to put the heart and emotion into five or six years ago.
“The Good Stuff”?
“The Good Stuff,” or “A Lot of Things Different,” or “I Remember.” I couldn’t have sung [Bruce Springsteen’s] “One Step Up” six years ago. Not and made it believable.
You’re being marketed as a sex symbol. Are you comfortable with that?
I don’t hate it. That’s part of that change that I made. I have a trainer out here, and he monitors everything I eat. I also work out for two hours a day, because we put on a pretty high-energy rock-style show. My body is shaped a lot differently than it was even a year and a half ago. I’ve lost 35 or 40 pounds, for starters.
“I wonder, What’s it going to take to turn them on? How are you goin’ to make them want to go home and make love, or make love in the car before they get home?”
You mentioned song sense. You couldn’t find a better song than “A Lot of Things Different.” How did you feel when you first heard it?
I thought it was one of the top two or three songs I’d heard since I came to Nashville. Dean Dillon [the song’s cowriter, with Bill Anderson] played it for me on his guitar, and he almost couldn’t get through it for cryin’. I knew it was a song that could change a lot of lives. Maybe somebody will love their kids more, or try again before breaking up, or even get the hell out.
I think I learned more about myself on this album. I’ve seen sides of myself that even I didn’t know were there. Every song’s got a little bit of me in it, and I know why I recorded it and where it lives in little rooms in my heart.
“Dreams,” about a woman who discovers men her age want someone younger, is an unusual song for country music. You were brought up mostly by a single mother and her female relatives. Do you think that’s allowed you to be more sensitive to women?
No doubt about it. It made me respect women more. That definitely helped me write “Dreams,” because everybody wants to be loved. Mom worked very hard, had a tough time, and went through a lot in her love life. She got divorced twice, and she was in love with a guy who died. One night she called me and said, “The more you know about love, the harder it is to find.” I wrote the song around that line, because there are a lot of people like that in their forties and fifties. Hell, I’m like that, and I’m 34. Right after I wrote it, I played it for her, and she just died. Then she played it for my Aunt Sharon after church on Easter Sunday, and she played it for my grandmother, and on down the line.
Your father wasn’t totally absent though, right?
Not totally absent. But I didn’t grow up with my father. My parents divorced a year and a half after I was born. My mom remarried and my stepfather raised me. My relationship with my dad revolved around sports. We went to a lot of Tennessee football games together, and he paid for college, but he wasn’t really the father figure.
In some ways the Kenny Chesney childhood experience parallels that of your friend Tim McGraw [who as a child didn’t know his father, former Mets all-star pitcher Tug McGraw].
Oh, it’s scary, our lives are so similar. We both love sports, we both lived with a single mother, and we both grew up without our father. It goes on and on, from loving Keith Whitley and George Strait to having people tell you that you ain’t going to make it in the music business. And we’re both out here playin’ 20,000-seat arenas. Weird.
How far back does this go?
I was on Capricorn when [Tim’s hit] “Indian Outlaw” came out. He called me and said, “Man, I’m really scared. If ’Indian Outlaw’ doesn’t work…” He was a half-song away from going back to Louisiana. Nobody wanted to put that song out, but Tim’s pretty stubborn, and he’s going to do things his way. So he had his epiphany too.
Did he coach you to keep your spirits up?
No, because our friendship wasn’t what it is now. I was on the road playing clubs, and he was doin’ David Letterman, you know?
You’re gaining on him now. Will that affect the friendship?
I don’t think so. When my album debuted at No. 1 on the pop chart, Tim was the first person to call me. He was almost crying on the phone. But Tim is very secure with himself. He knows he ain’t goin’ anywhere.
The one difference between you and Tim is that you haven’t found your Faith Hill yet. Yet you have a song, “On the Coast of Somewhere Beautiful,” about a girl that you just can’t get out of your mind.
Yeah. The first summer I moved to Nashville, I played this grungy bar…. It isn’t there anymore.
One of those dives populated by prostitutes and cowboys?
Right. But they all loved me. At first it was a little spooky, but I got to know those people. You look past a dirty shirt and you can find a helluva guy. I wouldn’t trade that experience for anything. I just made a will, and a couple of people I met down there are in it. They’re probably living at the mission these days.
Anyway, that summer I met a girl who made my heart jump for the first time. But she moved away because she loved the ocean, and her heart was with the dolphins, not the cowboys. She’s still livin’ at the beach, and she’s still got a piece of my heart. “On the Coast of Somewhere Beautiful” is about her, even though I didn’t write the song.
Most of the songs on this latest Kenny Chesney album are about your ex-fiancee, Mandy Weals. You seem to have a lot of feelings for her, even though you broke up several years ago.
Mandy and I are better friends now than we’ve ever been. That’s a miracle after all we’ve been through. I’ve done so much to hurt her, and she did a lot to hurt me. We would break up, get back together, then break up again. Three years of that went by, and it exhausted us mentally and emotionally. That’s why we finally said, “Forget it.”
What’s the biggest lesson you’ve learned?
In my next relationship I’m going to do everything I can to make that person feel secure. I didn’t do that with Mandy. I couldn’t imagine tryin’ to be secure around me right now. There are a lot of screaming women out there, and a lot of temptation.
Were you faithful to her?
I was faithful, but the day she moved out of my house, I went and slept with an ol’ girl that I had known before. The day! Shoot, I was pissed off and hurt and just wanted to kick her in the butt one more time. And she knew, believe me. I wouldn’t do that again.
On the other hand, you told her she was not going to be first in your life, that your career had to come first.
And she wouldn’t be first now, but she’d be more than second. There is a part of me that won’t let anybody get close to me like Mandy did.
How do you deal with women who throw themselves at you?
Everybody is more mature about it out here now. But you’ve got to realize, I was the guy in high school who never had a lot of dates. I quit growing when I was a freshman, and when I was in college all the girls dated the football players, not the kid playin’ rhythm guitar in a bluegrass band. Then when I got a hit and went on the road, all these really good-lookin’ girls wanted to have sex with me. That’s a trap that every [country star] has gotten into, because all those guys grew up just like I did. When I was datin’ Mandy, she was on the road with me, so the girls weren’t a factor. But when we broke up, I got into a little phase where I was ragin’ pretty good. Then I woke up one day and decided that was not why we got on the bus to come out here. So that changed a lot about how we do business. Don’t get me wrong. I love girls and I am single. But I’m not ragin’ like I was.
What do you look for in a woman?
Oh, well, she has to have a good personality, and she has to fit in no matter what the situation. She also has to love to lie around on the beach all day, because I think God might want me to be a beach bum. She has to be passionate about music too. Music keeps your soul young and allows you to have a free spirit. Of course she has to be passionate about families, and she has to be a pretty intense lover.
Did your mother tell you about sex?
No, we never had the sex talk.
Was sex confusing to Kenny Chesney as a kid? Or did the idea of it make you want to go out and have it right away?
I think a little bit of everything. But once you do it, there’s no turning back. It’s like chocolate cake. One bite’s not enough.
When you lost your virginity, did it scare you?
Yeah.
What — the fear of getting the girl pregnant?
Yeah, and the newness of it. It was unbelievable. Mine was a pretty redneck way to lose your virginity. It was uneventful, but redneck all the same.
Are you comfortable saying how it happened?
Not on the record. I was really young. We were drinkin’ whiskey. It seemed like a good idea at the time.
One theory about the sexes is that men give love to get sex and women give sex to get love. Do you think that that’s true?
That’s a helluva song title. It seems that way. Women get guys to think with a different head than women do, and women are more emotional than men. So I think that’s a pretty fair statement.
Do you separate sex and love, or do you need both of those together?
I’ve had sex with girls I could care less about. But to have somebody you can’t get enough of is really wonderful. Me and Mandy had that. We just didn’t communicate.
Do you think there’s a way to work things out with her?
I think we’re scared to go through it again. We’re better off taking a sigh of relief, because we’ve been broken up as long as we dated. I’m a pretty happy guy for the first time in years. When we broke up, there were two summers when I was unbearable to be around. Tim [McGraw] said, “Kenny, you’re not going to be any good to anybody until you make yourself happy. Nobody can do it for you.”
How did you do it?
I let a lot of anger and hurt go. If Mandy and I got back together, we’d be more prepared to get married now than when we were engaged. God almighty, you can’t go through what we went through and be the same person.
You have a hat that says “Be As You Are.” Is that significant to you? Has that become an official Kenny Chesney motto?
I bought it in the islands, and I wrote a song about it. It’s just about my lifestyle, and about this bar called The Quiet Mon. I sat there with a bunch of my friends and thought, I’ve got two double-platinum records and five or six No. 1 records, and nobody in this room cares. That’s why I love it down there. I had this conversation with Jimmy Buffett today. He said, “Man, I lived on a boat for a year, and I played that little bar, and nobody knew who I was. It was awesome.”
I really understand that. The islands had a big part in me becoming happy. If somebody really wants to get to know me, the islands are the best place to do it.
When you look back on your life, what do you hope to see?
Friends. To be able to share everything that has happened and to make new friends along the way. It’s important to me to enjoy it. I know a few guys out here who have taken this ride I’m taking, and the tragedy is that they never enjoyed a minute of it. I don’t know a lot of happy artists, really. But I’m fairly happy. And when this is all said and done, I want to look back and say I enjoyed it and I made a lot of great friends along the way.
This article came up in Penthouse some 20 years ago now, as you can see. Since that time, Kenny Chesney has received 87 nominations from the Academy of Country Music Awards and the American Music Awards, winning 21 times in that span. Oddly, Mr. Chesney’s only Grammy came for “Best Opera Recording” in 1995 — a fact our reporter really missed the boat on by not asking about, in our (almost never) humble opinion. These days he of course has a website with various tour information (and schwag), but he even has his own station on SiriusXM called “No Shoes Radio.” … At least one of us here spends a good deal of time on that station trekking back and forth across Southern California, by the way. That would be the smart one (and very likely this editor) in case you were curious. Who really likes shoes anyway?
