Kenny Chesney Remembers Jimmy Buffett With ‘A Pirate Looks at Forty’

The country superstar, whose own beachy songs owe a debt to the late songwriter, posted a video of him singing the Buffett ballad with the message “Sail on Sailor”

Kenny Chesney, whose own beach-forward country songs owe a debt to the tropical vibes of Jimmy Buffett, paid tribute to the “Margaritaville” songwriter with a solo performance of “A Pirate Looks at Forty.” Buffett died Friday at 76.

Seated on some island beach with only his guitar, Chesney sings the first verse and chorus of Buffett’s reflective 1974 ballad about a life well lived. At the end, he looks at the camera, blows a kiss, and says, “We miss you, Jimmy Buffett. Thank you for your friendship.”

Chesney posted the video, and another clip of him singing “Margaritaville” with Buffett, along with the message: “So goodbye Jimmy. Thanks for your friendship and the songs I will carry in my heart forever. Sail On Sailor.”


The pair teamed up for Chesney’s 2018 album Song for the Saints on an update of “Trying to Reason With Hurricane Season,” a Buffett song that first appeared on his 1974 album A1A. Chesney also joined Buffett, alongside country stars like Alan Jackson and George Strait, on a version of Hank Williams’ “Hey Good Lookin’” for Buffett’s 2004 License to Chill LP.

Buffett became a north star for contemporary country music, influencing the genre’s party vibes and teaming up with stars like Zac Brown Band on “Knee Deep” and Alan Jackson on the drinking smash “It’s Five O’Clock Somewhere.”


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