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“It’s a Different Kind of Freedom”: Kenny Chesney Opens Up About the Meaning Behind His New ‘Carry On’ Video

May 14, 2026 2:50 pm GMT

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Ahead of releasing the official music video for his new song, ‘Carry On’, Kenny Chesney has shed some light on what he hopes fans will take away from the forthcoming visuals, as well as outlining the meaning and inspiration behind the Shaun Silva-directed video.

Chesney reflects, “Key West isn’t about who you are, but what’s in your soul. It’s the great equalizer, with wisdom to be found just about anywhere if you listen. I knew I wanted this video to show people that heart - beyond what tourists see - and give them a sense of what this song’s really reaching into in terms of how to live”.

The ‘No Shoes, No Shirt, No Problems’ hitmaker candidly expands, “It’s a different kind of freedom. People here aren’t running after anything, but letting go of all that – and hanging onto what makes them happy. That’s the deal, really. It’s what I wanted this video to represent, and what I think reflects how this song hits me”.

At the moment, Chesney has only released a Lyric Video for ‘Carry On’ - which immediately received support from 158 out of 158 Country Radio stations - but we're keeping our fingers crossed we don't have to wait too long before the official visuals arrive.

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Fans can look forward to a special guest star in the form of David Wegman, the iconic Key West artist and sailor who features prominently in Chesney's book, HEART*LIFE*MUSIC.

Chesney warmly emphasises why it was important to include his friend in this new Key West-themed video for ‘Carry On’, “If you want to understand making the most of every day, of filling your time with creativity and laughter and adventure, David Wegman is all of that, and more. When we started filming, I wanted him to be part of this, so people could see what ‘Carry On’ draws from. We had the best day shooting at his place, where you never know if you’ll find painters, musicians on tour or just friends from somewhere around the world… But that’s what makes it so awesome. Open your arms and just welcome what life brings you”.

Florida's Key West has long been a muse for Chesney, along with other trailblazing artists, most notably the late great Jimmy Buffett, who shared Chesney's penchant for a life lived near the coast, in the sunshine and with a cold drink to hand. We're sure the ‘Carry On’ will capture this joyful, creative, glass-half-full spirit that permeates both Key West itself and Chesney's sunny, galvanising discography.

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Written by Maxim Mower
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