"And I leased out the Hooters corporate jet. It had Hooters on the side. Had, 8:30 in the morning, we had Hooters girls in there dressed in a uniform, in their uniforms. We had curly fries, we had hot wings, we had beer. And the whole plane was full of that," he recalls.
The trip has become a tradition. At tour's end last September, he upped the ante, giving all 100 members of his crew bonus checks of nearly $14,000.
By the time they arrived in St John, the party was well underway.
For Chesney however, the celebration was bittersweet—just seven months earlier he had been reluctant to go on tour at all.
"To be honest with you, Anderson, I just wasn't ready to go do it. You know, with everything that happened in my personal life it was an awful period for everybody," he says.
Chesney is talking about his relationship with actress Renee Zellweger. They met in January 2005, married in May, and split in September. It seemed they had no chance from the start.
"I remember coming back from the wedding and we landed in Little Rock, Arkansas. I had a show. We didn't have a honeymoon, you know? Welcome to Little Rock, baby. Happy Honeymoon," he says, laughing.
The marriage ended before the tour did. Zellweger insisted on an annulment, not a divorce. On the paperwork she cited fraud, igniting months of Internet and tabloid speculation suggesting Chesney was gay. Rumors he initially refused to comment about.
"Maybe I should have come out and said 'No I'm not,' but I didn't want to draw any more attention to it, you know, cause I knew I wasn't and I didn't have to prove to anybody that I wasn't, you know, I didn't feel like I really did," Chesney tells Cooper. "It's not true. Period."
Asked why Zellweger cited fraud, Chesney says, "We thought was the least harmful was fraud cause it's kind of broad, whatever it is. Doesn't specify. And, boy, didn't, we were wrong. But, it's okay. The only fraud that was committed was me thinking that I knew what it was like. That I really understood what it was like to be married and I really didn't."
Chesney says he has no regrets about getting married. "Not one bit. Even though I'd sit here and say 'I wish we'd gotten divorced instead of all that annulment stuff' and saved me a lot of public humiliation and I still don't have any regrets. I mean…I loved her, you know? And it was real."
He says he wants to try marriage again. He would like to have kids, but for now, the road is where his life and his career are. When one tour is ending, Chesney is already planning the next one.
"You are obsessive compulsive about planning, and what comes next. And keeping it going," Cooper remarks.
"I am. I'll admit I'm a workaholic," he says. "Because I'm constantly thinking how I'm gonna do it better."
Produced By John Hamlin