Kenny Chesney Pays Tribute to Jimmy Buffett with Emotional Oceanside Performance

“Sail On Sailor”….


Lauren Jo Black

| Posted on

September 2, 2023

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Kenny Chesney, Jimmy Buffett; Photos Courtesy Instagram

Kenny Chesney honored his late dear friend Jimmy Buffett with a poignant tribute on Saturday morning (Sept. 2), just hours after the “Margaritaville” singer’s passing.

The country superstar took to social media to pay homage to his longtime friend with a special Oceanside performance in Key West, Florida.

“So goodbye Jimmy. Thanks for your friendship and the songs I will carry in my heart forever. Sail On Sailor 🦜🌴🌊,” Chesney captioned the somber clip, which features him performing a Jimmy Buffett classic.

With his acoustic guitar in hand, he skillfully strums the tune’s chords and pours his heart into a rendition of Jimmy Buffett’s “A Pirate Looks At Forty,” a track first released on Buffett’s 1974 album, A1A

As waves crashed ashore and with the sun rising behind him, Kenny Chesney offered an emotion-filled performance of the tune.

“Mother, mother ocean, I have heard you call/ Wanted to sail upon your waters since I was three feet tall/ You’ve seen it all, you’ve seen it all/ Watched the men who rode you switch from sails to steam/ And in your belly, you hold the treasures few have ever seen/ Most of ’em dream, most of ’em dream/ Yes I am a pirate,” Chesney sings in the clip.

Kenny Chesney and Jimmy Buffett have a long history together. Chesney first gave Buffett a shoutout in his 1998 hit “How Forever Feels.” 

Later, in 2004 Buffett, Chesney, Clint Black, Alan Jackson, Toby Keith, and George Strait released a collaborative cover of Hank Williams’ “Hey, Good Lookin’” for Buffett’s License To Chill album. 

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In September of 2018, Chesney and Buffett joined forces for a new song, titled “Trying To Reason With Hurricane Season,” as Hurricane Irma began to pummel the Caribbean. 

“To me, that song is just true poetry and a true reflection of Jimmy’s ability to tell a story and to capture a moment and to paint a picture of that moment,” Chesney shares. ”As I was in there recording that song, it hit me that I’m not sure that Jimmy gets the credit he deserves as being a poet, like a true songwriter storyteller, poet, a lot like Hemmingway was in his time, Tennessee Williams, and a lot of people that, to me, they’re just great storytellers. I truly believe that Jimmy’s one of those guys, and if you listen to this song, it stamps a moment in his life and it paints just such an unbelievable picture and how relevant that song is all these years later to what’s happening now. So that being said, I mean, it was just special to be in the studio recording that song that Jimmy had written about his reality.”

Through the years, Kenny Chesney and Jimmy Buffett teamed up several times for impromptu performances at local Key West and Nashville establishments.

Additionally, Buffett and Chesney have a mutual friend in 10-time CMA Musician of the Year, Mac McAnally. McAnally is a longtime member of Buffett’s Coral Reefer Band.   

Mac McAnally, Kenny Chesney, Jimmy Buffett; Photo Courtesy Instagram
Mac McAnally, Kenny Chesney, Jimmy Buffett; Photo Courtesy Instagram

Jimmy Buffett, the beloved “Margaritaville” singer and leader of the Parrotheads, passed away at the age of 76 years old. 

According to a statement shared on Saturday morning (Sept. 2) via Buffett’s social media, the singer/songwriter passed away late Friday evening (Sept. 1). 

“Jimmy passed away peacefully on the night of September 1st surrounded by his family, friends, music and dogs,” the statement read. “He lived his life like a song till the very last breath and will be missed beyond measure by so many.”

While his cause of death is unclear, Buffett has been battling an undisclosed illness since 2022. Most recently, he was forced to reschedule a concert in May after being hospitalized to address medical issues that need “immediate attention.”

In September of 2022, Jimmy Buffett canceled his entire tour and his team revealed that he would not be touring for the remainder of the year due to “due to health issues” and a “brief hospitalization.” 

Buffett, whose real name is James William Buffett, was born on December 25, 1946, in Pascagoula, Mississippi and raised in Alabama. He moved to Nashville to pursue a career in music in the late 1960s and also spent most of his time in New Orleans and Key West. 

Jimmy Buffett’s musical career began in the late 1960s, and he soon became known for his unique blend of country, folk, and Gulf Coast rock, often referred to as “Gulf and Western.” 

In 1970, he released his debut album titled Down To Earth. Nevertheless, it wasn’t until 1977, with the release of his seventh studio album, Changes in Latitudes, Changes in Attitudes, that Jimmy Buffett and his band The Coral Reefers catapulted into mainstream fame, thanks to the project’s hit single “Margaritaville.”

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“Margaritaville” has gone on to become a massive, world renowned hit and was even included on The Recording Industry Association Of America’s list of Songs Of The Century. 

With his signature laid-back style and a guitar in hand, he enchanted audiences worldwide, transporting them to a world of sun-soaked beaches, swaying palm trees, and carefree days.

His timeless hits like “Fins,” “Come Monday,” “Margaritaville,” “Cheeseburger in Paradise,” and “Changes in Latitudes, Changes in Attitudes” became anthems of escapism and celebration, evoking the spirit of a never-ending beachside vacation.

Throughout his career, Jimmy Buffett has collaborated with several country artists, including Alan Jackson, Clint Black, Kenny Chesney, Toby Keith, Zac Brown Band and George Strait.

Beyond his chart-topping success, Jimmy Buffett was a prolific songwriter, author, and actor. 

Photo Courtesy Jimmy Buffett
Photo Courtesy Jimmy Buffett

He has released several novels, including Tales from Margaritaville and A Salty Piece of Land, which offered fans a deeper insight into the characters and stories behind his music. Buffett’s engaging storytelling also extended to the big screen, where he appeared in films such as Rancho Deluxe and Hoot.

Buffett’s indomitable spirit of adventure led him to explore diverse interests, from piloting planes and sailing the seas to founding the Margaritaville brand in 1985. The Margaritaville brand encompasses restaurants, hotels, and a lifestyle empire, all embodying his laid-back philosophy. 

Thanks to his lucrative businesses, Buffett was named one of the richest musicians in the world, with an estimated net worth of $1 billion, by Forbes as well as added to the World’s Billionaire List.

Jimmy Buffett’s philanthropic endeavors were equally admirable. He dedicated himself to environmental conservation, particularly marine and coastal protection, and established the “Save the Manatee Club” to safeguard the beloved aquatic creatures he cherished.

Buffett’s live performances were legendary, drawing thousands of fans, known as the Parrotheads, from all corners of the globe. His annual tours were more than concerts; they were vibrant celebrations of life, love, and the pursuit of happiness.

Jimmy Buffett is survived by his wife of over 40 years, Jane Slagsvol, and children Savannah Buffett, Sarah Delaney Buffett and Cameron Marley Buffett. 

He was expected to release his new album, Equal Strain On All Parts, later this year, which would serve as the follow-up to their 2020 project, Life On The Flip Side. It is now unclear if the project will still be released.

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Lauren Jo Black

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Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.