Meet Hillbilly Rock Star Kenny Chesney

Talks About His Brief Marriage To Renee Zellweger, And The Rumors That Followed

(CBS)  Often, he even joins the afternoon tailgating that is part of the Kenny Chesney concert experience. And backstage it’s more of the same, there are a couple of fully stocked and well-used bars. Even the production office is in a Tiki hut.

Among the eight busloads of roadies and 17 semi-trucks of equipment Chesney tours with, there’s one 18-wheeler full of nothing but Caribbean props.

"It creates an unbelievable atmosphere. And that’s one of the reasons why, that’s one of the reasons why, that’s one of the ways," he says.

"Critics will say, 'Well, look. You are an invention of marketing in some ways.' That you created this image, created this lifestyle brand around it. And that's as much as a part of your success as the music," Cooper says.

"I do sell fun. I know we do that. There’s no doubt about it," Chesney says. "And I will admit that I have allowed my love for the tropics to get into my music. "

Asked how he sells fun, Chesney tells Cooper, "Every night, when I'm on stage, and I do a song called 'No shoes, no shirt, no problems' and every night I told them, I said, 'I know we've all got problems. Whatever is going on in your world, don't think about it for the next two hours and just have some fun, and let's listen to music.' And yeah, I marketed that. I'm…I promise you."

It has worked so well, Chesney can now afford to call the U.S. Virgin Islands his home for several months each year. He first came to St. John to shoot a video eight years ago.

He’s now in his third home, and is a fixture with the locals. In the restaurants and bars, he’s a regular.

But oddly, his favorite spot is the back alley of a burger joint. He calls it "the executive suite."

"Back here with propane tanks, ice makers, brooms," he says. "For some reason or another, I feel so relaxed back here, and I know. It's odd. And I love it, man. I mean it's almost like, it's therapy for me to come back here and just sit."

"If this is the executive suite, what does it say about the corporation?" Cooper asks, with a reply of laughter.

The "corporation" was formed in the hill country north of Knoxville, Tenn. In high school, football and baseball consumed him. But when he got to college at East Tennessee State, he started playing guitar cover songs in the bars around campus.

"I had a tip jar and on the front of the tip jar sitting on a stool, it says: 'Tips welcome. But anything by James Taylor, Jimmy Buffet, or especially Free Bird, is $25.' Because I was so sick of hearing it," Chesney remembers.

"Everyone wanna hear 'Free Bird' or 'Buffet!' You know or whatever. And I loved those guys, too. So I hope they're not too mad at me. And people would get drunk, though, and pay it," he says.

After college, he got a record contract but didn’t get noticed much. That is, until he took a chance on a song even he admits is silly. The title: "She Thinks My Tractor's Sexy."

"I knew that a lot of people that grew up just like I did would go crazy over it. But it was a song that was…there was no gray area with that song. Either you loved it or you hated it. You know what I mean? But it was a great groove," Chesney remembers. "I was smart enough to record that song but I was smart enough also not to record another one."

As it turns out, Chesney actually has two tractors but says they are "not one bit" sexy.