Kenny Chesney is an eight-time Entertainer of the Year.
Hold on to your cowboy hats...we're getting up close and personal with country's rock star—Kenny Chesney!

The eight-time Entertainer of the Year has sold more concert tickets than any other person on the planet—and is currently gearing up for his eighth summer tour.

Although he's appearing on The Oprah Show on his birthday, Kenny has a gift for the audience—an intimate concert! 

Kenny Chesney talks about touring.
Every night is an once-in-a-lifetime experience, he says. "It's a shared moment for a couple of hours with a group of people that will never be that group of people ever again," Kenny says. "You might play that city again next year, but if the energy is great, it's a shared moment that you won't ever [have again]." 

See how Kenny gets ready for a tour  Watch

Kenny says he hits the road with a set list but will change it up if there's a great crowd. "There were several nights last year where we took our set from two hours, 15 minutes to past three hours," he says. "There's just something magical that happens sometimes onstage where it's almost an out-of-body experience, and the connection that you have with the crowd—you don't ever want that connection to stop."
Kenny Chesney says he sometimes has a drink with fans.
Sometimes, Kenny says. "I think it creates an unbelievable environment for our show," he says. "I'm a big Aerosmith fan, and when I was going to Aerosmith concerts when I was in college, if Steven Tyler came out to the parking lot and gave me a drink, I don't think I'd ever forget it."

Whether he's chilling in the parking lot or burning it up on stage, Kenny says he wants people to have the time of their lives. "Over the years I've tried to find ways to enhance the experience and make it really something memorable," he says. "I want to be able to give all I can."

Find out why Kenny feels more comfortable onstage than off  Watch

Kenny Chesney on what he learned from sports
A coach once told Kenny that the game isn't won on the field—it's the hours of preparation before that really matter. Kenny says he tries to approach what he does like an athlete.

"I love sports because you have to work hard," he says. "I think I got that from family, the way we were brought up. We never had anything given to us, and I think that a lot of that comes into play in what I do. I can't do anything halfway."

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Kenny Chesney shares the advice he got from Bruce Springsteen
Toward the end of his tour a few years ago, Kenny says Bruce visited him backstage in New Jersey—
and gave him some of the best advice he's ever received. "He said it took him until he was 41 to figure out that you can start a song on a piece of paper, and you can put that piece of paper and that song in a drawer, and you can open that drawer two years from now and that song, that piece of paper will still be there," Kenny says. "He goes, 'Your life ain't like that.'"

Kenny says Bruce told him to pay more attention to his life outside touring. "He said, 'Everything you're experiencing out here on the road, it's really, really great ... [but] it's a little bit of an illusion as far as what real life is.'"

Kenny Chesney says he'd like to settle down someday.
It's a possibility, Kenny says. "I don't think that the next 20 years of my life is going to revolve around sound checks, tour buses and a catering truck," .

There's definitely room for a woman in his life, but Kenny says she'd have to like living on a tour bus for part of the year. "I don't run [my life] right now that well," he says. "It kind of runs me better than I run it."

No matter what, Kenny says he's having a blast. "Oh my God. How can you not?" he says. "I love what I do."

Kenny Chesney on success
Kenny says he could have never dreamed where his life has taken him. "When I first started this, I was just a kid wanting a song on the radio," he says. "When I was at college at East Tennessee State University playing on a stool like this with a tip jar in front of me, I didn't know I would be doing Oprah on my birthday. Who thinks of that?"

Go backstage with Kenny and find out what's playing on his iPod  Watch

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The sweet sounds of Sugarland


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