At age 19, a small-town Southern boy from Luttrell, Tennessee, got a guitar for Christmas and learned to play. He spent years singing and strumming at honky-tonk bars across the South, dreaming of the day he'd hear his songs on the radio.
Twenty years, 30 million albums, eight Entertainer of the Year awards and countless sold-out concerts later, Kenny Chesney is now one of country music's biggest superstars. In the past decade, this self-described hillbilly rock star has sold more concert tickets than anyone in the world.
As his legions of loyal fans know, a Kenny Chesney concert is an experience. Sure, you'll sing along to his multiplatinum hits—"She Thinks My Tractor's Sexy," "When the Sun Goes Down" and many more—but that's not all. At some tour stops, Kenny parties alongside concertgoers at preshow tailgates.
Now, Kenny says he hopes to get even closer to his fans by singing his heart out and sharing his private thoughts in his debut documentary, Kenny Chesney: Summer in 3D. In the film, Kenny shares his affection for the men and women who helped make him a star. "They come by land, on boats, and they love every minute of it. So much so, you want to get out there with them, and when you do, even more of them keep coming," he says in the film. "Honestly, it blows me away."
After the last stop of his sold-out summer tour in 2009, Kenny says he planned to take time off and recharge, but instead, he started production on his documentary. "Not only am I in this film," he says, "I made it."
Kenny and his crew pieced together footage from six concerts, including stops in Boston, Philadelphia, San Francisco and Seattle. All along, Kenny says he did it for the fans who've stuck with him since his debut album hit stores in 1991.
"[My fans and I] have such a unique relationship. I feel like it's a very unique love an affair that I've had with them for a long time," he says. "There's a large group of people ... [who] grew up with me and have dreamed this dream with me."
Some nights when Kenny is onstage, he says he wishes every person in the crowd could see what he sees and feel what he feels. "That would be the most incredible thing," he says. "And that's why I did this."
In Kenny Chesney: Summer in 3D, Kenny reveals his preshow rituals. Before every concert, Kenny says he gathers with his band, friends and family in a place known as "the vibe room."
"The room is totally designed for us to get ready to go onstage," he says. "To me, that's where the show starts. It doesn't start at 9:15 when the music starts. It's a place for me to get mentally in the right spot and to remember why we came and to flush everything out in your mind that could be bothering you."
Some nights, Kenny says the connection with his fans is so strong, it's almost as if nothing else exists. "When I'm onstage and I'm in front of those people, it's a revival," he says. "It's as if I'm in an out-of-body experience."
As soon as he straps on his guitar and strums the first chord, Kenny says he tries to give his audience everything he's got. "I have to really be in the moment, because I feel like there's a kid out there in that audience somewhere [and it] might be his first concert ever, in his whole life," he says. "If I do my job, that kid may have music in his life forever."
In one of the most poignant moments of the documentary, Kenny's fans join voices and sing a few lines of the song "Better as a Memory" after Kenny becomes too overcome with emotion to get the words out.
The lyrics are: "Move on like a sinner's prayer. Let go like a levee breaks. Walk away as if I don't care. Learn to shoulder my mistakes." Kenny says these words summed up how he was feeling at that moment.
"I was in the process of backing away from this a little bit. All the fans knew. The crew people knew...knew that this year, I was not going to tour like I had in the past," he says. "I almost sang those lines, and I realized that every emotion that I was feeling had just come up, and I just couldn't sing."
At that time, Kenny says he felt mentally exhausted and needed time away from his music. "I feel differently now, I promise," he says. "But there was something in the back of my mind that says, 'I don't know when, if ever, that I'll do this again.'"
When you devote all your time and creativity to one passion, Kenny says life can start to feel mechanical. "Music's not supposed to be that way. Music's supposed to come from [the heart]," he says. "I felt like that if it ever got mechanical, I was going to back away from it. And it did last year."
Kenny's grueling schedule and intense passion for music leaves little time for much else, including relationships. In September 2005, Kenny made headlines when his four-month marriage to actress Renée Zellweger was annulled. Now, he reveals what really happened.
Oprah: Is that why your relationship with Renée Zellweger failed?
Kenny: You know, one of them. That and the fact that I panicked.
Oprah: You panicked?
Kenny: Yes, I panicked about a lot, you know.
Oprah: After you got married you panicked?
Kenny: Yes, but, you know, I look at my life as a box. ... So everything that I put in—learn how to play guitar, put that in the box. The friends I made. I put that in the box, and my career grew. Everything around me—all of the awards and all of the songs I wrote and all the success and everything—I put in that box. That box built grew into this wonderful house. Okay? And you protect everything and all the relationships and all the people that helped you build that house. And this is the first time I've actually talked about it, but that's what happened. I protected that box.
Oprah: So where was the marriage? In the box or out of the box?
Kenny: It was out of the box. Oh my God, but it's tough. It really is tough. And she's a sweet soul, no doubt about it, but I just wasn't ready.
Kenny has traveled the world and performed alongside artists like Dave Matthews. He even sang for President George W. Bush at the White House. But he still has a few dreams left for himself and his family.
With Oprah Show cameras in tow, Kenny heads to Tennessee to check one item off his list. Even though Kenny owns a private jet, his grandmother, Lucy Grigsby, has never flown in an airplane. "That's about to change," he says. "We are going to go to Florida Keys, and we're going to go to my favorite restaurant [Blue Heaven], eat some key lime pie and have some fun."
Kenny hops in his SUV and drives to his grandma's house to pick her up. "Coming home is always a welcome break," he says. "I love that I can walk in here and just be 12 years old again."
Despite some preflight jitters, Lucy climbs aboard Kenny's plane and buckles up. "I didn't think I'd ever do this," she says. "I just always thought I'd be afraid."
After an unforgettable day of sunshine, sand and key lime pie, Kenny and his family head back to Tennessee. "I'm getting as much out of it as she is, I promise you," he says. "Being with my grandmother feeds my soul."
Music will always be part of Kenny's life, but he says the new dream he has for himself is to get married and have children.
"I'm always going to want to write songs and get out and play them for somebody," he says. "But, yes, I could see me settling [down] at some point."