There’s an old joke that goes like this: What happens when you play a country song backward? CHESNEY: Yeah, but it doesn’t look like “Oh, please come buy me,” either. Sometimes we’d play a club on tour, and it would be just me and the band and the bartenders. CHESNEY: I don’t really lose my temper that much, but when somebody mistreats my guys, I just go crazy. I was in a fraternity, but I was so zoned in on music that I didn’t go to many parties. PLAYBOY: What did you do on your first night in Nashville? I’m sure it went in the trash can as soon as class was over. “This isn’t country music.” He meant it as a slam, but we took it as a compliment. CHESNEY: Yeah, but they’re not the kind of record Alan Jackson or George Strait would consider country. CHESNEY: The moment my life changed was about 1999, with , when I found my own niche.
You get your wife back, your dog back and your truck back. I always have, even in my school pictures when I was a little kid. I hate album covers where people are just smiling so big. PLAYBOY: How do you get through a night like that without giving up? 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 was just making enough money to go to Taco Bell every day. I did throw a Play Station out the window of my tour bus one night. 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. A lot of people would ask me if I ever thought about doing music for a living, and I’d say no. CHESNEY: I watched TV because I’d moved to town on January 12, 1991—the day Congress voted to support the Gulf war. I’m a country singer just by how I grew up, who my parents are and my heritage. Just because I don’t sing about the normal country themes doesn’t mean my songs aren’t country. PLAYBOY: What are some normal country themes you avoid? I’d been on the road since 1993, so for six or seven years I was trying to be somebody else.
Country has evolved a lot since that joke was first told. It’s like a neon sign that says PLEASE COME BUY ME. People were eating chips, drinking beer and not listening to me. We play on Play Station 3, and I’m very competitive. CHESNEY: I got into a fight with a guy from a radio station around 1995, maybe in Fort Myers, Florida. He got into a fight with one of my guys, so I got all redneck on him. CHESNEY: Yeah, but I had probably ,000 or ,000 in expenses, with gas and salaries. PLAYBOY: What was the best night you ever had in college with the tip jar? BUT ANYTHING BY JAMES TAYLOR OR JIMMY BUFFETT IS . So that one night I must have played a bunch of James Taylor songs. At one point I probably knew 400 or 500 songs off the top of my head. I got a degree in advertising and marketing but didn’t know what I was going to do. My family and friends thought this was something I was going to try and then go back home. 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. I wrote a song called “Amy,” and I wish I hadn’t written it. If Lynyrd Skynyrd came out today, it would be considered country; same with the Eagles. CHESNEY: I do sing about drinking, but it’s in a party way. “Yeah, he’s selling out stadiums everywhere, but it ain’t really country music.” I love traditional country music. Record labels today are much less patient: Artists have a bad record, and they’re gone.
If you play a Chesney song backward, you come home from the islands, sober up and feel as blue as the water off St. 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. PLAYBOY: Right here we have the cover of every CD you’ve released.  By 1995 I was getting gas money, a shower and food—that’s what we got paid. 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. PLAYBOY: So how much money would you guess you made in 1995? CHESNEY: I was in love with the music of Bruce Springsteen, Willie Nelson, Roger Miller. I’d play “Every Rose Has Its Thorn” by Poison every now and then when people requested it. We were able to piece a show together that was really high energy, with an hour and a half of rocking music. PLAYBOY: If we drug-tested you, what would we find?
Country music began in the South, but Chesney has taken it even farther south, down near the equator. Everybody wonders why you’re so messed up as a person. I loved Buffett’s storytelling and the first couple of John Mellencamp records, Elton John. PLAYBOY: Did playing music make you a star in college? 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. Sometimes, on very rare occasions, a seventh gear rears its head. Especially with today’s cell-phone cameras, there’s no win to it. PLAYBOY: In the early days you drank a lot more before a show? CHESNEY: Lunesta, which is a sleeping pill, and fever-blister medicine, because I had a cold sore from the sun and stress.
He has won country music’s entertainer-of-the-year title eight times and sold more than 30 million records. I love getting paid to do it, and I love getting on my boat after I get paid to do it. Being famous is uncomfortable because I grew up very simply. You used steel drums and congas, which are usually heard more in calypso than in country. CHESNEY: No, especially after I had two albums that sold 4 million copies each. CHESNEY: I was in a cocoon for almost two weeks before my birthday, making , the record I have out now. CHESNEY: The gear system was invented by me and my boat captain, Ben. A couple of weeks ago when I was down on my boat in the Virgin Islands, I reached seventh gear. 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. CHESNEY: I don’t know that I ever went on tipsy, but I would always come off a little tipsy.
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. PLAYBOY: So you want attention only when you’re onstage, and once you’re offstage, you don’t want it. Everything revolved around friends, family, church and sports.  A lot of buddies I went to high school and college with actually work for me now. On the road, in my bunk, I sleep better than I do anywhere else in the world. I earned the right to make a record any way I wanted. 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. The next day I decided to fly home and get off the island for a bit. 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.
No musician has sold more concert tickets in the 21st century. PLAYBOY: But there must have been a lot of kids in Knoxville who never left. PLAYBOY: So part of you wasn’t content with simple. CHESNEY: I used to go out in my backyard at night and stare up at the sky and wonder what was out there. PLAYBOY: That probably makes it difficult to settle into domesticity. I had a lot of fun in my 30s, probably more fun than should have been allowed. PLAYBOY: If feeling a little tipsy is first gear, what is seventh gear? PLAYBOY: When was the last time you drank so much you vomited? We played the Pittsburgh Steelers’ football stadium in the summer and had a big blowout after the show.
“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. 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? CHESNEY: I have friends who have a normal family, kids and a dog, and I think I would blow my brains out. But I’m such a free spirit, I feel more alive when I’ve got somewhere to go. But I had a big party here in Nashville, with about 300 people. 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. I can stay on my boat for a few weeks if I have a guitar and a girl and a Bob Marley CD. My friends Tim Mc Graw and Faith Hill came to it, a lot of industry people, a lot of family. 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. 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. To say you’re more comfortable playing in front of 20,000 or 30,000 people than not? 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. The album felt as if it had been recorded by a beach bum—it was relaxed, tan, refreshed. I’m pretty simple except for the fact that I have a really great boat and a little bit of money. In place of country’s traditional steel guitars and fiddles, Chesney used tropical steel drums and congas. I will never let anybody call a restaurant and say, “We’re with Kenny Chesney. When I’m offstage I don’t feel like the person everybody sees.