Kenny Chesney may sing about kicking back with “No Shoes, No Shirt, No Problems,” but the place where he feels most relaxed isn’t a beach — it’s the stage.
The country superstar, 57, says there’s no place he feels more at ease than performing in front of thousands of fans, guitar in hand, music blaring.
“I know this sounds crazy, but to be in front of 60,000 people on stage — that is where I feel the most comfortable in my life,” Chesney told People. “For two hours, nobody can mess with me or the band.”
“It’s just us giving the audience everything we have, and the audience giving everything back,” the “Don’t Blink” singer continued.
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“That is one of the most unbelievable feelings I’ve ever felt in my life. It’s my drug of choice,” Chesney said.
No Regrets
With more than 30 No. 1 hits and decades on the road, Chesney has built a career few could dream of — and says he wouldn’t trade it for anything.
“I don’t regret giving my whole adult life to creating — because what a way to live,” he said. “That’s what I’ve always done.”
And he’s not slowing down anytime soon. Chesney will return to Las Vegas for another residency at The Sphere, launch a new book tour, and already knows what his schedule looks like through 2027.
His New Book + What Really Matters
Chesney’s upcoming book, Heart Life Music (out Nov. 4), gives fans a deeper look into his life, career, and passion for creating.
“I love what I do. I love making music,” he said. “And I love being on that stage more than any place in the world.”
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But even with all the success, Chesney admits love is still a work in progress.
“I don’t know if I’ve learned that much,” he added with a laugh. “I’ve been traveling for 30 years. But I think now, the thing I value most is authenticity — whether it’s in music or relationships.”
With no plans to hit pause, it’s clear that Kenny Chesney’s heart beats loudest on stage — and he wouldn’t have it any other way.
Heart Life Music is out Nov. 4 and available now for preorder.
What truly separates Chesney — a 2025 Country Music Hall of Fame inductee — from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney’s best were released after 2010. It’s there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.
We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.
Gallery Credit: Billy Dukes