“Jimmy Created Space for My Dream”: Kenny Chesney Shares How Jimmy Buffett Inspired Him to Make the Music He Wanted To Make

Kenny Chesney and Jimmy Buffett have long been kindred spirits, with both artists introducing a sun-soaked, island-inspired ambience into the country music landscape.

Jimmy pioneered this tropically-tinged Gulf and Western sound in the 70's and subsequent decades, with Kenny picking up the Tiki Bar baton and evolving it in the early 2000's.

What has always been refreshing about the Kenny-Jimmy axis is the fact that their respective catalogues share the same glass-half-full cri-de-coeur and joyful nature, while still being distinct. Jimmy has long been the poster-child for coastal living and carefree, margarita-fuelled days on the beach, with his music serving as a celebration of the kind of life he lived before his passing in September 2023.

Much of Kenny's music carries this same imagery, but the ‘No Shoes, No Shirt, No Problems’ hitmaker's discography has a subtle difference. More often than not, the Knoxville native is singing from the perspective of someone who is longing to live the life that Jimmy represents, epitomised by ‘The Life’ and ‘Somewhere in the Sun’.

As a result, Kenny's music has struck a resonant chord with those who couldn't be further from the sunny climes of the US Virgin Islands of Key West, but that yearn to be there.

In a new interview with Amanpour & Company, Kenny has reflected on just how impactful Jimmy has been throughout his career, but especially when he was starting out in the 90's. Initially, Kenny attempted to emulate the neo-traditional sound of George Strait, before feeling compelled to pivot towards Jimmy's Gulf and Western style.

Aptly, it was during the filming for his 1999 hit, ‘How Forever Feels’ - during which he declares, “Big orange ball, sinking in the water / Toes in the sand, couldn't get much hotter / Little umbrella shaped margaritas / Coconut oil, tanning señoritas / Oh, now I know how Jimmy Buffett feels” - that Kenny fell in love with the US Virgin Islands, the place that went on to define the next chapter of his music.

Kenny begins by touching on the eclectic palette of genres and sonic influences that enriched his childhood, “There was bluegrass early on...and on the way to school, I heard a lot of country music, but once I got into high school, I realized there was a group called Van Halen, and then I realized there was a group called Lynyrd Skynyrd. I realized there was ACDC. And then when I got into college is when I realized the genius of Bruce Springsteen, Jimmy Buffett and Bob Marley and The Wailers. Now, if it's possible to put all those acts into a stew, that would be my music, because I'm a true believer...what comes out of you as an adult is the direct reflection of the music that you digested early on in life”.

What makes this all the more moving is the fact that a lot of those early role models turned from icons into friends for Kenny, with the ‘I Go Back’ hitmaker collaborating with Jimmy and The Wailers, as well as becoming good buddies with Bruce Springsteen.

Kenny goes on to pay homage to the artist that influenced him more than any other, “When I first started in this business, first of all, Jimmy was the first one that taught me that it was possible on any level to paint pictures with words. And I didn't know that was possible, right? I was a kid from East Tennessee, but...Jimmy created space for my dream...Jimmy had a really big dream, and it showed me that, ‘Wow, I could have a big dream too’. And that's when I started to get really creative”.

He concludes by underlining how the people of the US Virgin Islands have been instrumental to building his tropical country brand, by highlighting to him that his music could relate to people beyond the confines of country music, “Never knowing that I was going to have a place in the US Virgin Islands and spend a lot of time down there. But when I did do that, I met a lot of people from a lot of different places, with different religious beliefs, different political beliefs. They just didn't grow up like I did. A lot of them were from New England, and from all over the world, and the longer I was down there, the more that I realized that I don't just have to make music for people that are in the genre of country. I can make music for everyone. And that's that's how much of a profound impact it had on me as an artist, as a creative person, and it really changed my life in a lot of ways”.

Much like Jimmy, Kenny has made an effort to give back to the communities in the Virgin Islands that have offered him so much inspiration. When Hurricane Irma caused devastation across the region, the five-time CMA and ACM Entertainer of the Year decided to dedicate his 17th studio album, Songs for the Saints, to the islands, and to set up the ’Love for Love City’ fund to help rebuild from the wreckage.

It captures the loving, kind and joie-de-vivre-infused lifeblood underpinning Kenny's No Shoes Nation fanbase, which has grown to symbolise so much more than the music.

As Jimmy did before him with his dedicated Parrotheads, Kenny has built No Shoes Nation around a pirate-flag representing the sunny, celebratory and authentic way of life he summaries on his 2020 anthem, ‘Happy Does’, “Happy is as happy does / Grab a six-string, find a rope swing / Hang a palm tree in your truck / Drink a beer just because / Steal a slow dance in a rainstorm / And a kiss from who you love / Laugh and live with a half-full cup / Yeah, happy is as happy does”.

It's a shame that Kenny and Jimmy won't have the opportunity to collaborate any further and continue their joint mission of promoting this rum-powered, beachside lifestyle. Thankfully, though, we got the chance to witness them link up on now-iconic tracks such as ‘Trying to Reason with Hurricane Season’ and ‘License to Chill’.

When Kenny offered a poignant tribute to Jimmy during the 2023 CMA Awards with a performance of ‘A Pirate Looks at Forty’ alongside Jimmy's longstanding friend and Coral Reefer Band-member, Mac McAnally, it showcased the ‘Margaritaville’ legend's ongoing impact on Kenny's musical journey. As Kenny's latest album, BORN, and his new book with Holly Gleason, HEART*LIFE*MUSIC, both show, Jimmy's infectious, ebullient spirit will continue to colour Kenny's creativity for many years to come. And when the time comes, it'll be fascinating to see which member of the newer generation will take that crucial Tiki Bar baton from Kenny, and introduce Gulf and Western to a whole new frontier.

Watch Kenny Chesney's full interview with Walter Isaacson for Amanpour & Company below:

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