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Kenny Chesney Recalls Speed Bumps on Road to the Top

Noel Vasquez, Getty Images

It’s hard to believe, given his record-breaking sales and countless accolades, but Kenny Chesney‘s career path was not always smooth sailing.

“We all get caught up in the idea of, ‘We want this now,‘ and I was no different,” Kenny recalls to Billboard of his anxious early days in the business. “I had a few hit records, and there were other people having hit records and they were getting paid $2500 more than I was getting paid … I remember talking to [my manager] Dale Morris going, ‘Why are we doing this? Why are we doing that? Why isn’t this happening?’ That mentality was one of the reasons that we’re doing what we’re doing today. That taught me patience and that everybody is in this together, and we’re going to take this and make it wonderful and not just live for the moment. Dale called it: ‘We’re betting on what’s to come, not what’s right now.’ And that’s hard. When you’re a kid, you want it all right now.”

Kenny soon channeled his energy into making his live show “something special.” “Whether it worked or whether it didn’t, I was going to do it,” he said. “It wasn’t safe and it wasn’t probably the smartest thing to do, but it was the smartest thing to do for me. I got a taste of the George Strait stadium tours and I was going to do whatever it takes.”

At the time, ‘How Forever Feels‘ was blowing up the charts and became a six-week No. 1 record. A song that resonated with his audience, Kenny was more determined than ever.

“I remember going offstage and talking to everybody involved in my life and said, ‘Wait and see. Give me two or three years,’” he revealed. “Everybody in my life at that time invested with me. And that was the secret. Everybody was on the same page. It was all we had. We didn’t have other people or booking agents, or other managers with hidden agendas or anyone who wanted to make a deal because they wanted to get rich quick. We were all in it together. So, when that happened we had a chance to have something special still. When I invested and everybody saw that I mentally, physically, monetarily, emotionally invested into this, everybody did it with me.”

After this was done, Kenny was finally able to give fans his all. “We feel that it’s really important to give people the best show they could possibly get, not just mine – the whole package, for the least amount of money possible,” he asserted. “We can charge a lot of money and they’ll come one or two times but they may not come back. So, we try to find that balance of doing it the right way and still having people come year after year.”

Granted, he figured that out by watching the King. “Where I first learned that and where I first saw how cool that could be, when all the stars aligned, was my first year on the Strait tour,” Kenny recalled. “I had a lot of records out at the time and when I’d do all the songs people would go, ‘Oh yeah, that’s the guy that sings all those songs.’ People hadn’t connected yet. I was the second guy on and then there were the Dixie Chicks, Faith Hill, Tim McGraw and George Strait. All this music and it was unbelievable. I was a fan. I would get offstage, go take a shower and I would go watch everybody from the side of the stage. That was my first moment of realizing, ‘This is how it’s done.’ I learned a lot. I remember sitting on the side of the stage taking mental notes and thinking, ‘If I ever get to do this. This way, this is how I want to do it.’

And he did. “Every stadium show I do … I go to the very top, the very back row and I take in the environment and I take in the atmosphere and take mental notes: ‘This is how far I’ve got to go,’” he said. “I see it from my perspective. I see what it looks from the stage to the back door, but I want to see how it looks from the back door to the stage because that’s where they’re going to sit. Some nights are better than others. When you have those moments where nothing goes wrong it’s just beautiful. It’s like you can do anything. It’s almost like an out of body experience. You feel like another version of yourself because it’s so good.”

You can see how Kenny puts together a show for yourself on his current tour. The next stop is July 8 in Denver. Get a full list of dates here.

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