“Pirate Flag” by Kenny Chesney

Grade: C

photo by Danny Clinch/Sony Music Nashville

After releasing the most serious, substantial work of his career—the dazzling “You and Tequila,” “Come Over” and “El Cerrito Place”—Kenny Chesney returns to the type of be-who-you-are anthem that helped establish him as both a reliable radio hit machine and a summertime brand. But “Pirate Flag,” the debut single from his upcoming album, Life on a Rock, due April 30, feels like Kenny is taking a barefooted step back. 

While part of the island hopper’s undeniable charm lies in his genuine affection for the wayward beach life, the pirate imagery has worn thin. Clichés about sipping rum, blowing sails and flying the Jolly Roger are all crammed in like messages in a bottle (which, of course, are also mentioned), making you wonder if the tune’s writers—the usually rock-solid David Lee Murphy and Ross Copperman—might have at one point considered adding a yo ho ho or two. 

The groove and Kenny’s rhythmic delivery evoke Tom Petty’s “Mary Jane’s Last Dance,” and it’s certainly easy to picture fans singing along when it’s blaring out of tailgate parties before Kenny’s shows this summer. But by the time the Caribbean cowboy repeats how he traded in a sedentary life for one with a pirate flag and an island girl, even those very fans may think they’ve heard this one before.

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