Cole Swindell Reveals the Kenny Chesney Song He Picked to Play at First-Ever Live Show

by Matthew Wilson

Cole Swindell plays for thousands of fans at packed-out concerts across the country. But when he first started out, he struggled to play for 12 people at a bar. The singer admitted his nerves got the best of him the first time that he took the stage.

Since then, Swindell has played countless songs thousands of times, including many he wrote himself. But he still remembers the first song he ever sang at a Georgia bar. Speaking on The Marty Smith Podcast at Outsider Studios, Swindell discussed his first time behind the mic. The singer broke out “Don’t Happen Twice,” by Kenny Chesney at the bar.

“I didn’t know what I wanted to do, so me and my buddy started playing in bars there,” Swindell says. “I always knew how much [music] meant to me. But I just never realized what it would be like to be on the stage. I’ll never forget my first show at a place called Locos in Statesboro, Georgia. Me and my buddy Burt, the first song we ever played was Kenny Chesney’s ‘Don’t Happen Twice.'”

Things probably didn’t go how Swindell expected. He was less of a superstar and more of someone struggling to deal with a ball of anxiety. “I was so nervous I could barely breathe, much less sing,” he says. But Swindell stuck with it. And through practice and repetition eventually, those nerves melted away.

Cole Swindell Meets Kenny Chesney

But the story doesn’t end there. Cole Swindell got to meet and even perform alongside Kenny Chesney years later. He went on tour with Chesney and Jason Aldean playing at packed-out stadiums. Swindell decided to tell Chesney about singing his song all those years ago.

“I got to tell that story to Kenny years later down the road,” Swindell says. “It was the year I toured with [Jason] Aldean so we got to do the stadium tour with Kenny that year. I got to tell Kenny that story, and his response was ‘Oh really, we got to get you up and do it one night.'”

Chesney decided to give Swindell a second chance at covering the song. Swindell took the stage in front of thousands to sing the song. This time he didn’t let his nerves get the best of him.

“I’ll never forget in Seattle where the Seahawks play, one night he got me up and I got to sing the song,” Swindell continues. “The first song I ever sang at my first gig in front of 70- 80 – however many thousands of people at the football stadium. And all I could think about was, no joke, god I hope I get to somewhere like Kenny so I can help somebody else like that. That was the reason I wanted to be on stage and later came the writing.”