As Kenny Chesney's first headlining tour progressed, he became more and more intrigued watching his fans tailgate before his show. One day, in 2002, he decided to join them.

"It started purely out of boredom. There are only so many hours you can sit on the bus and watch TV or play basketball or whatever we do to pass the time before we go out onstage," Kenny admits to Billboard.

"One day we were playing the Amphitheater in Pittsburgh, and it was about halfway through my first year of headlining. My bus was parked on this hill, and I could see all the tailgaters and everybody out there. It was this whole other world out there, so I said, 'I'm gonna go out there in the middle of it and see it!

"It started to be the thing I would do every single day," Kenny continues. "The next year, our tour was called the 'Margaritas 'N Senoritas Tour' so I had the idea that I was going to make a pitcher of margaritas and take it out there and give it to the craziest fans I saw. So we did that all year and that was a lot of fun. The next few years, everybody knew we did that and it became a lot of work. Now, we do it every now and then. We don't announce it; we just go in and out."

Kenny can relate to his fans' excitement when he joins them tailgating. In fact, it was putting himself in his fans' shoes that gave him the idea to surprise them before shows.

"I'm a huge Aerosmith fan," he explains. "If I was out there with my buddies hanging out, having a few beers before the show and Steven Tyler rolled up and gave me a margarita, I'd never forget it. So that was something that I thought about."

Immensely appreciative of his own fans, Kenny says they often mirror himself.

"They are incredibly passionate, hard-working, fun loving, life loving, music loving bunch of people. They reflect me a lot. Me and my band and crew have always lived by the code: 'Work hard, play harder.' We do that, and I think our fans do that," he says. "The group of people who see us play every summer really reflect me and my attitude and I like that a lot. I'm very proud of the diversity of people that are coming out to our shows and I see that. It's so amazing to watch. There are kids 8 to 80 out there, and they're all singing along. They know every word and it shows you they're not just listening to the songs on the radio, it's literally part of their life. I never would have imagined that would be the case."

Click here to see where you can sing along with Kenny on tour this summer.

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