Smoky Mountain (Beach) Boy: 10 Prime Kenny Chesney Classics

Eight-time Entertainer of the Year Celebrates His 51st Year in the Sun

Kenny Chesney hails from the same region of East Tennessee that gifted country music with such luminaries as Roy Acuff, Chet Atkins, Dolly Parton, Carl Smith and Tennessee Ernie Ford.

But early in his ascent to superstardom, Chesney — who turns 51 today — decided he preferred the sun, sand and surf of the tropics to the rocks, ravines and rattlesnakes of his native Smoky Mountains. Naturally enough, he’s incorporated those preferences into many of his songs and music videos.

Happy birthday, Kenny, and smooth sailing.

Here are 10 songs — some party anthems, some pensive ballads — in which Chesney displays his margarita creds:

  • “She’s Got it All” (1997, written by Craig Wiseman, Drew Womack)

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    There’s nothing in the lyrics here to suggest the tropics, but the video is set in a desert eatery and bar, where the favorite condiments are “Kenny Chesney’s Lethal Lightnin’ Sauce” and sweet señoritas.

  • “How Forever Feels” (1998, Wendell Mobley, Tony Mullins)

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    Chesney bares his muscular chest to show just how buff he is for the beach as he’s confronted by an aboriginal archer, a fake palm tree, girls wearing abbreviated garb and wildly colored wigs and parrots on his shoulders. There are also scenes in which he soaks up the sun and water without his usual headgear. Is he guilty of having too much fun? You be the judge.

  • “No Shoes, No Shirt, No Problems” (2003, Casey Beathard)

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    “The notion of no shoes, no shirt, no problems isn’t a song title,” says Chesney in the video’s intro, “but a way of life, my way of life, where I feel the most alive, where I feel the most settled.” Then come the idyllic clips of Chesney wading in the surf, piloting his boat and leading a night-time jam on the beach. If any problem is imaginable in this Paradise, it would be keeping the guitars in tune in all that damp air.

  • “When the Sun Goes Down” (2004, Brett James)

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    After Chesney routs Uncle Kracker from his wench-filled trailer on the beach, the two divide their time between singing about nature’s wonders and leering at them as they flit by like grass-skirted fireflies. Steel guitars meet steel drums. Life could be worse. But those leis and pukka shells have to go.

  • “Old Blue Chair” (2004, Kenny Chesney)

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    No parties going on here. And no crowds. Just a pensive Chesney walking in the sand and singing about the battered old beach chair from which he likes to views the world. He’s a modern-day Robinson Crusoe, alone on his island until a bikinied Girl Friday enters briefly to topple him out of his chair and his reverie.

  • “Living in Fast Forward” (2006, David Lee Murphy, Rivers Rutherford)

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    You can search these lyrics high and low and not find a single sand or sea reference. But the video makes up for it with scenes of Chesney on his yacht and frolicking at the water’s edge. As the song says, he’s a “hillbilly rock star out of control”—and having a helluva good time at it. The video tucks the beach shots between scenes of him playing to roaring, stadium-size crowds. Included, as well, is a glimpse of Chesney kissing Gretchen Wilson’s hand.

  • “Beer in Mexico” (2007, Kenny Chesney)

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    Why is Chesney having “another beer in Mexico,” when there are plenty of perfectly good brewskis right here at home? Well, he says, he’s at the stage where he’s too young for this and too old for that and needs to make some life decisions. Should he marry or stay single? Too big a question. But one thing’s clear: he absolutely needs to have another beer and “let the warm air melt these blues away.” If only he had his old blue cheer for comfort—or maybe the lass in the bikini.

  • “You and Tequila” (2011, Matraca Berg, Deana Carter)

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    Ah, the double addiction of bad love and great Patron! But what better place is there to come to terms with one’s weaknesses than on the wave-churning coast of California — along which Chesney and singing partner Grace Potter thrust and parry like amorous birds of prey.

  • “Pirate Flag” (2013, Ross Copperman, David Lee Murphy)

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    This song is strictly biographical — from Chesney’s tip of the hat to his Smoky Mountains home town to his trading it in “for a whole ‘nother world/a pirate flag and an island girl.” The video has its share of pirate flag waving, but the beauty of it is watching Chesney enchant a huge crowd. By the way, are those real palm trees we see in the background or just part of the spectacle?

  • “Bar at the End of the World” (2017, J. T. Harding, Aimee Mayo, David Lee Murphy)

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    There’s no helpful video to energize this tune. Fortunately, it provides its own “selfies” via a trove of seafaring images—ropes, boats, sea shells, the stars as guides and that much-heralded beach adornment—a girl in a T-shirt. Haven’t we seen her somewhere before?

Edward Morris is a veteran of country music journalism. He lives in Nashville, Tennessee, and is a frequent contributor to CMT.com.