Kenny Chesney Says He Didn’t Realize What Was Possible For His Career Until He Opened For George Strait

Not a bad guy to take lessons from.

These days Kenny Chesney is known for being one of the best entertainers in country music. A member of the Country Music Hall of Fame with 33 #1 hits in his stacked catalog, Chesney is arguably as big as he’s ever been in his three-decade career thanks to his incredible live shows and his ability to use his “No Shoes Nation” brand to rocket himself from just another country artist into a cultural icon.

But early in his career, before he became a stadium headliner and a brand all to himself, Chesney admits that he struggled to find his identity.

During an interview with the Wall Street Journal ahead of the release of his upcoming book, Heart Life Music, Chesney says that the ’90s were a rough time for him:

“Looking back on it, I wasn’t ready. I wasn’t comfortable in my skin as a songwriter, as a performer, as an interpreter of songs. So yeah, the 1990s were an awkward time for me as an artist.”

Of course Kenny had some massive hits as an artist in the ’90s with songs like his first #1 hit, “She’s Got It All,” “That’s Why I’m Here,” “How Forever Feels” and “She Thinks My Tractor’s Sexy.” But he was still trying to figure out who he really was – and what was even possible.

That’s when Kenny got an opportunity that opened his eyes to what was really possible for him and his career.

In 1999, Chesney went out on tour with the King of Country Music himself, George Strait, opening for him on his George Strait Country Music Festival Tour. (The tour also included openers like the Tim McGraw, the Dixie Chicks, Mark Wills, and Jo Dee Messina. Talk about stacked).

And it’s as he was playing those stadiums with George Strait that Kenny realized what he could do in his own career:

“We didn’t know what else was possible until we went on the road with George Strait. Opening my first stadium tour for him, I saw what was possible.”

Now, I’m sure any artist will tell you that seeing what’s possible and actually getting there are two very different things, something that requires not only hard work but also some good fortune along the way. And Kenny is never one who’s been afraid of hard work. (I mean, just look at the muscles on that dude…)

But even he admits that he was nervous when he embarked on his own headlining tour for the first time:

“I thought it was a terrible idea. We were in Albuquerque at a pool party at the hotel, and Louis Messina, my concert promoter, and Clint Higham, my manager, came up to me, went, “OK, next year, you’re going to go out and headline your own tour.” I said, “You guys are f-ing crazy.” I’ve been on the road at that point for years opening for everybody. We built an audience, but I just didn’t feel like I was ready.

I decided, “if we fail, we fail.” They’re going to expect us to fail anyway, right? Nobody believed in us. And that’s where focus became robotic. I was constantly working and writing songs and constantly thinking of ways to connect with the audience and grow it.”

(An interesting observation here: Nearly 30 years later, Kenny is still with Messina Touring Group, his concert promoter from his first headlining tour. In a “what have you done for me lately” business where relationships are key, it says a lot for both Kenny and his promoter that the relationship is still going strong after all these years).

Well obviously Kenny didn’t fail. Quite the opposite, actually: He’s STILL headlining stadiums and cranking out new music, and even recently announced that he’s heading back to Las Vegas to headline the Sphere for the second time in as many years.

And all it took was some inspiration from George Strait to open his eyes to what was possible.The post Kenny Chesney Says He Didn’t Realize What Was Possible For His Career Until He Opened For George Strait first appeared on Whiskey Riff.