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Kenny Chesney wins Entertainer of the Year
© Kenny Chesney/Melanie Dunea
Kenny Chesney wins Entertainer of the Year
Kenny Chesney: Laid-Back...but Driven

Second greatest hits album and another massive tour keep him in overdrive

MSN Music

Don't let the easy-going demeanor or beach-casual fashion sense fool you: Kenny Chesney is a driven man.

Related: See photos of Kenny Chesney
More: See the ACM Awards Hunks (and Hotties)

The Tennessee native's albums are now reliably gilded on release, with 11 of his 13 releases to date certified gold or platinum, and his figurative mantel is likewise laden with dozens of awards from the Country Music Association, the Academy of Country Music, Country Music Television and other barometers of country superstardom. His last three national tours have clinched Chesney's standing as a live music heavyweight who sells a million tickets each tour.

If he's relaxed in conversation, Chesney doesn't hide the tenacity displayed when he first picked up a guitar as a college freshman--within a year, he was playing for classmates at Eastern Tenn. State University and enrolled in its bluegrass program, cutting his first self-released recordings before graduating. When his first commercial release via an established label was undermined by the company's demise, Chesney rebounded with a new deal, a new album and his first Top 10 country singles in a pace largely unbroken since.

Looking back over a 15 year career, Chesney spends less time reflecting on past glories than he does gauging future goals. MSN recently caught up with Chesney in anticipation of his "Greatest Hits II" album, out May 19, and between the early dates on his Sun City Carnival Tour, slated to bring his live show to arenas and stadiums across the country.

MSN Music: You released your first hits package in 2000. When did you realize you'd amassed enough new hits to justify a new set?

Kenny Chesney: Probably a couple of years ago. I didn't really want it to be just songs that we had since the last one. I wanted it to reflect a period, and I think that a couple of years ago I thought that we might be getting to that spot. And now, especially, since we released the 'No Shirt, No Shoes, No Problems' album in 2002, it's been an incredible chapter in my life.

I think the songs on here are more than just songs people heard on the radio...There's a couple of songs on here like "Be As You Are," that wasn't really a single but it needed to be on this because it was a part of a record that was really personal to me, the "Songs from an Old Blue Chair" album. [Editor's note: Chesney's "Be As You Are: Songs from an Old Blue Chair" was released as a self-professed "side project" without singles, yet debuted at #1 on the country charts and proved a critical hit. ]

The new set points up your ongoing openness to collaborating with artists outside the Nashville mainstream, including Dave Matthews and Uncle Cracker, as well as your recent #1 with veteran country singer-songwriter Mac McAnally. When you started out in the mid-'90s, did you put such high-profile duets on your career plan?

Not really. When I started out in the '90s, to be honest with you, I didn't really have much of a game plan. I was just trying to get started. I was just a kid from East Tennessee wanting to get his record played on the radio. I really was trying to get to a point where I could do this the way I wanted to do it in my head. I didn't necessarily know how to get there or how to go about it. It really just happened organically over time.

Collaborating with some of the people I've collaborated with was never in my head. I never even thought about it. But over time and throughout the years, I've met people and realized I have a certain commonality with some really talented, creative people. And being able to work with Mac McAnally on "Down the Road."

The "I'm Alive" song with Dave Matthews is really special, because he and I have gotten to know each other over the last several years, and we really have a lot of respect for each other, especially as songwriters, musicians and on the touring end. That's where we met, on the road, and Dave and I have a lot of the same fans coming to see us live. Doing this song with him was unique for me, and him. Still, I think when people hear this song, even though we come from very different parts of the world and different backgrounds, him from South Africa and I'm from East Tennessee, somehow it works.

You've been a four-time winner of both the ACM and CMA Entertainer of the Year honors, deemed the most prestigious award for either organization. Last fall during the CMA Awards, you commented that you had never dreamed you'd reach those heights when you were starting out. But you also acknowledged a healthy sense of competition since then. Do you still set high goals?

You know, I do musically. I'm still very driven. I'm very focused. I still don't feel like I've written my best song yet. I hope I haven't. And I still feel like as a band, the guys and I can get a lot better. I still think that even though we've achieved a lot, even though I've had a lot of success, I still feel as though every night that I go on the stage it's a new stage and a new crowd and a new night. I still feel like we have something to prove every time we go onstage--to give the fans the best experience they can possibly have.

That drives me more than anything, more than awards, more than money. Both are great. But it would be really hard for me to know that I put on a show that was just OK and made a lot of money. You know? (Laughs) ... I feel like me and the band have something to prove every night. I still feel like we can make better records. I still feel like I can get better as an artist, and as a person. You know, things that have nothing to do with awards.

Given how much you've focused on live performance, it's clear that's a key part. Would you say your live shows may say as much or even more about who you are?

I'd agree with that. I believe we are the epitome of a live act. I tour when I've got a record coming out, and I tour when I don't have a record coming out. It's just a part of my life, and a part of all our lives who are out there. My crew guys have been with me a long time, my band has been with me a long time. Before they were with me, the crew guys were part of some pretty big tours--with Van Halen, with the Stones, with the Police when they were hot--and those guys have seen a lot of things and they've taught me a lot about how to do this. It's been fun to learn from them. Still, they've seen all this happen with me, and it's their dream, too...So the live thing is really a life -- I just cut a record in the middle of it. (Laughs.)

You're gearing up for your Sun City Carnival Tour, another big summer tour capped by at least a dozen stadium engagements. How do you go about upping the ante with each new tour and differentiating the experience?

I think the key part is trying to give the fans the best experience you can. We differentiate ourselves each year in that aspect. We have the songs that we have. The band knows the songs. We don't rehearse the songs. What we try and rehearse is what you just said: to make the songs different, to hit some buttons so that when the fans leave they feel like they got their money's worth... Because, man, I'll tell you what, you don't want to be up there and have some kid come to your show [and fall short]...That might be the first show he's been to, and you've got a short period of time to maybe make that kid love music for the rest of his life. If you didn't do your job, you've lost him forever. And if you did do your job, you've got him forever.

You've line up some showstoppers as opening acts including Sugarland and Miranda Lambert . How do you go about choosing those artists?

Well, conventional wisdom would say they've got to be successful and they've got to have some hits on the radio. But, more than that, they've got to bring more than just hits. They've got to bring a personality to the stage. And they have to bring kind of a factor you can't put your finger on. I've had people out on the road who had a lot of hits who put the crowd to sleep, basically. And even though it doesn't, in a selfish way I feel like it reflects on my tour. I think Sugarland is great...Miranda Lambert ...hasn't had a lot of hits, but when she goes onstage she has an energy you can't put your finger on. I think people connect with her. And that's why I'm going to love having her out there... Montgomery Gentry were on earlier tours, and when they go onstage, they're going to bring a certain energy level to what they do, and to what we do.

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Related: See photos of Kenny Chesney
More: See the ACM Awards Hunks (and Hotties)

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