Though certainly not always the case, sometimes, it doesn’t take much stretching of the imagination to draw a straight line from contemporary artists back to the older generations who directly inspired them. Johnny Cash and Colter Wall come to mind. So, too, do Kacey Musgraves and Dolly Parton. And indeed, where would “When the Sun Goes Down” singer Kenny Chesney be without the early influence of Margaritaville Mayor himself, Jimmy Buffett? The connection between these two sun-loving stars isn’t lost on their audiences, nor is it lost on Chesney.
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In a 2025 interview with People, the “Old Blue Chair” singer recalled the night that Buffett unknowingly changed his life. In the early 1990s, Chesney was a recent East Tennessee State graduate and Nashville transplant when he attended his first Jimmy Buffett show at Starwood Amphitheater. Having just graduated from college and still struggling to make ends meet, Chesney sat up in the grass. “Where you go when you can’t afford a real seat,” he added. “That night changed my life.”
“I’d never seen anything like it,” Chesney continued. “For someone to give so much love from the stage and connect with an audience like that. I was lying in bed at night, going, ‘Wow. I can’t believe what I just saw.’ And then you fast forward, and it’s surreal that you become friends with that person and collaborate with that person in the studio and have that person just really inspire you. That’s what Jimmy was for me.”
Years later, Chesney would get the rare opportunity to become friends with his musical hero.
Kenny Chesney Shares His Favorite Jimmy Buffett Story
Where else would a story about Kenny Chesney and Jimmy Buffett take place but Key West, Florida? The southernmost city of the United States served as the backdrop for what Chesney called his favorite Buffett story, which he recounted in his memoir, Heart Life Music. According to Chesney, Buffett called the singer and asked him if he wanted to work in the studio over the holiday break. The night before the session, Buffett invited Chesney out to an Italian restaurant on Duval Street. “It’s the old part of town,” Buffett said over the phone. “You’ll love this place.”
And he was right. Chesney describes the night with a sense of immense respect, admiration, and awe that not only was he getting to work with Buffett, but he was also hearing the “Come Monday” singer tell stories about pirates sailing off the Florida coast, Ernest Hemingway, Shel Silverstein, and other notable figures associated with Key West. “Generous with his memories, it was an immersion course in the currency of things you cannot buy,” Chesney wrote. As if the dinner with his musical hero wasn’t enough of a “pinch me” moment, after they were done eating, Buffett ushered Chesney outside to show him something.
“As we’d ordered our meal, the annual Key West Christmas Parade had begun,” Chesney wrote. “Walking outside, we were in the midst of it. All the crazy pomp, colorful costumes, the drill teams, and marching bands flowed down the street. It was brilliant, buoyant, and free. What a special way to be introduced to the local soul of Key West. I felt the spirit of what was. I’ve never been so grateful to see through someone’s eyes.”
Photo by Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images
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