"I never look at the crowd to see what kind of crowd I have. I want to feel them when I walk out on stage," says Chesney.
"Once I get up on that elevator, and I get up and get that adrenaline flowing through me, it all makes sense at that moment, why we're there."
Last June, he became the first entertainer since Michael Jackson to sell out Knoxville's Neyland Stadium. And it was the biggest moment in the 35-year-old Tennessee native's career.
"That's the moment that I finally felt like all the radio tours that I did, all the promotion, all the eating at truck stops at 2 a.m., all the being away from home ... Every single thing that I worked for and dreamed about ... at that moment I felt it came together for the first time," he says.
When the show's over, Chesney escapes to the last place you'd expect to find a country superstar. He makes his home in the Caribbean islands, where he aspires to live, as the song says, with "No Shoes, No Shirt and No Problems."
"This is my island therapy," says Chesney. "To come out here, bartend, tell some jokes, hang out with the locals ... I love it."
But life hasn't always been this sweet. Born in Luttrell, Tenn., Chesney's parents divorced when he was a toddler, leaving his mother to raise him and his sister alone. He was in college before he even picked up a guitar. And at first, it looked like he might not have a reason to keep playing.
"Early on, we didn't have anybody coming to see us. We didn't have anybody buying our records. We couldn't get anybody to play our records," says Chesney.
To make ends meet, he worked on Nashville's Music Row, writing songs for other singers. Over the years, he put out albums regularly, but none of them made much of a splash. And out on the road, he was merely the warm-up for more successful acts.
"It was really tough," recalls Chesney. "There were guys out there, I felt like I was just as good as them. I really started to question myself after that."
So the former marketing major decided the best way to win fans was simply to work harder, promote his music endlessly, and play for anyone who would listen. And for more than 10 years, slowly but surely, Chesney built a loyal audience.
Despite a nearly unstoppable drive, Chesney says he is learning to loosen up. And he credits the Caribbean with helping him come into his own.
"I didn't really fully understand it until I started living on an island. Days turn into weeks, weeks turn into months, months turn into years down here. And you never really wanna go home," says Chesney.
"I tell you, being here just helps me be me more. If I can be me more, I can be a better songwriter. I think that down here, I find myself painting more pictures with words than I did before."
The critics have never been all that enthusiastic about his music, but Chesney only cares what his audience thinks. And these days, most of that audience is full of swooning women, who have turned the balding, 5-foot-6-inch crooner into an unlikely sex symbol.
Last year, he was named one of People magazine's sexiest people. "It was confusing," says Chesney. "'Cause I don't look in the mirror and see myself that way at all. I just don't."
He has a lot of women pursuing him right now. But how does he choose? "Very carefully," he says.
He's also careful not to give away too much of himself, especially after breaking off an engagement four years ago.
"It's not fun to get a broken heart. It's not fun to, you know to, really lose something you love," says Chesney. "Sometimes, love's not enough."
But Chesney's not quite saying whether he's still on the market.
"Well, you know, I wouldn't say that I'm 100 percent available," he says. "But I can tell you that I'm not ready to be married, either."
Last year, Chesney was nominated for two Country Music Association Awards, including country music's highest honor, Entertainer of the Year.