My Guitar Lesson with Kenny Chesney: Man Behind the Music

Kenny Chesney on Music, Love and Fame

Credit: ABC News

It's not every day that one gets a guitar lesson from a country music superstar, much less from Kenny Chesney.

But I did - not a bad job perk.

During our shoot for ABC News' "Nightline" at a sound stage in Nashville, Chesney taught me how to hold his guitar, then placed my fingers on the strings and helped me play a few chords.

"You're a natural," he told me.

Then he started to sing acappella, while I desperately tried to play the few notes I just learned.

"Sing," he said. But how do you sing in front of Kenny Chesney? I froze.

Chesney could not have been more courteous and, well, fun as he rehearsed and joked with his band, while they prepared for their "Brothers of the Sun" tour, which kicked off on June 2. The tour will hit 22 cities and travel nearly 20,000 miles with 20 tour buses and 80 tractor trailers.

His show literally takes a village. Chesney travels with a 283 person crew.

"We are one big, huge team," he said. "To get all those people to be focused, to do it like we do it is fun to watch. And we've got it down pretty good. I've got a lot of really great people around me that make it seem seamless."

Chesney is as entertaining behind the scenes as he is on stage. The man has boundless energy, which was evident throughout our day with him. If he wasn't checking his iPhone, he was chatting with our crew or bouncing around his house. But his focus was his new puppy, Pancho, who is Chesney's leading lady these days.

What was most striking about this multimillionaire is that he says he is afraid of failure, even after all his astounding success. This week, Chesney released his thirteenth album, "Welcome to the Fishbowl," a title he said came to him last summer while he was friends at a bar in Grayton Beach, Fla.

"It was packed and it was about 20 minutes of people coming up and saying hello to me and wanting to take a picture, an autograph, and one of the guys said, 'you know, we had no idea that it would be like this for you.' I said, 'Welcome to the fish bowl,'" Chesney said.

But the stage is where the country star is at peace, and Chesney said he becomes a different person in front of a crowd of tens of thousands of fans, than the man we witnessed in front of our cameras.

"When I'm up there, I have a certain swagger that I don't have when I'm like this, you know," he said. "I tried real hard over the years to leave that person up there. I try to leave that part, the ego and the swagger and what it takes to be that person onstage. And when I go back up there, I revisit that. And I revisit him, and we become that person again."

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