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.