Flying High With Kenny Chesney

Part 2 of "In the Spotlight With Robin Roberts."
7:55 | 11/08/11

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Transcript for Flying High With Kenny Chesney
You've got -- -- bodies that ever put on a cowboy hat and a cut off T shirt and his sports isn't half bad either. We're talking about Kenny Chesney. He -- -- parking cars the pumping out songs to selling more concert tickets and country. That any other artist this decade -- no surprise because boy. Does he know how to put on -- show. Party in the parking lot burgers on the grill and it irrepressible -- in the end -- Boston Gillette Stadium. We're new England's secret -- is about to -- its southern group. When the sun goes down as -- turns to night. All eyes -- to the -- this seed this man. The undisputed king of the road take this country -- sailing above the -- -- -- and he -- with all of the words of his song a little little. Have some -- He invited me to join him for. Both pulled out final stop of his sixty city record breaking -- Earlier that day I got it all access pass to his behind the scenes magic. You want all access. You're -- you know access. Show the -- the -- how. Does that work very uncomfortable. Every else. It's like every moment -- you -- energy. The crowd. You feel the energy of the band right from the speakers and not me that's amazing feeling and and -- across -- limelight right in the middle of all other side. -- -- And then. And then. Well my friend that is an interest. -- -- couldn't -- -- Now it was my turn that -- -- I'm scared -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- where did just that eleven it's they might add that. After flying high it was time for -- come back to earth and take another Iraq we're gonna go all of the Palestine -- when I knew where the show. He goes to the farthest point away from the stage. Knowing these are the fans he needs to reach they paid the least and he wants to give them the most. It's that same incessant spirit of giving that led him to take last year off. -- says the years of touring caught up with -- he walked away. In. Order to hold all how important was it for you -- a little time -- It was a necessity. I had invested so much Ramallah and two. The relationship called love affair with a plan to invest -- so much in my life but on the flip side and then they have invested. Yes and so much of their life and that investment to me. Was. On both ends wasn't worth protecting at all cost and that meant taking your way. Then that's -- you don't you don't go halfway and it's hard to turn yourself from perfect but went -- sometimes that. Testing is nonstop energy drives every aspect of this war from T shirt design the set design for backstage catering selected for the crew. To installing -- on -- burger grill for the ban. He even creates a -- given out of the crew at the end of every school. It's that level of dedication and natural talent at that -- to the top of the the award winning success. It is here at his home in Nashville -- comes to reflect and restore. Any invited our cameras and for the first time. You know what when I come home off the road -- this I can win out here -- -- Water and kind of relax in. Reflect on the weekend reflect on the show world -- my case now the year. And and it's just it's peaceful. But this bachelor sports photographs and music memorabilia. -- every quarter in his -- district. It is is that doesn't mean here. This is this is the general manager -- a former. In this is our very last. Football practice our last moment. The moments and memories of his life have always included sports. That -- and build a new creative outlet for the filmmaker. Last year he produced the ESPN football documentary. The boys of fall. Yet even as the son of a gospel singing -- it took the little boy from east Tennessee years to find his musical falling so when did you know. Wanted to do this wasn't I was in college and that was planted a couple places in Johnson City, Tennessee and I was making enough money -- -- -- go eat. -- -- -- Every now in one. That's a big deal and you know and I knew that it that this -- going to be a part of my life and had no obvious that you can't agreements. So -- about that time that national open its arms Hinton not at all I had the luxury. -- a luxury now that the time it was very frustrating but I had I had the luxury of not happening early. You know you -- is forced to overcome adversity. If you want to move along that was the definition of adversity early wrong. But boy when he did happen he happened -- Just these mega hit those shoes no shirt no problem is more than a song it's his musical -- -- delayed. Back live this former college marketing major mastered branding a never ending -- One thing that I'm very proud of the fact that -- that about it it's but we do their business to and what does is done will -- everybody else. But the life of the party has also seen down time the perennial bachelor -- was -- by the tabloids questioning his personal life. As they picked apart his short lived marriage to Oscar winning actress Renee Zellweger well past relationships will that have a bearing on. I think the room over I think -- violence. I hope you know. I don't well wooden. Arrival had a recorded a song longtime -- and a lot of things different now and of course -- not personal. We're in your beautiful. Homes -- gorgeous home. -- -- -- -- He ever envisioned having a family. Reason -- in -- of course. About I really don't envision. You know everything in my life revolving around sound check in catering -- -- I don't want that. We'll Soviet Union because you have this on let got and I still believing followed her -- think exist yet. Have I felt yes. And the -- -- -- it again. The biggest misconception about you and -- not. Both of you think -- just and is doing the best night and -- Being himself as what they love notes. As the Boston crowd sings along to -- the summertime. He's right where he belongs. On stage. At home with this thing. Is -- That I didn't feel like -- That had to be somewhere where. Does that come years. -- years of constant news. -- when I realize that many items belong everywhere. That's when I got little. Happier.

This transcript has been automatically generated and may not be 100% accurate.

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