Alongside the good company of Taylor Swift and Garth Brooks, he’s one of the only recipients of the CMA Pinnacle Award, which recognises artists that will have a “long-term positive impact on the appreciation of country music for generations to come”.

Chesney is synonymous with the beachside, island-inspired way of life that he champions on anthems such as ‘No Shoes, No Shirt, No Problems’, ‘Coastal’, ‘We Do’ and ‘Save It For A Rainy Day’.

But the Tennessee crooner first made his mark on the country charts with a much more traditional-leaning sound that was influenced by the likes of Garth Brooks and George Strait. Chesney’s first five albums were all released during the 90s, and spawned a slew of smooth, rose-tinted hits, such as ‘She’s Got It All’, ‘What I Need To Do’ and ‘You Had Me From Hello’ - along with the hilarious ‘She Thinks My Tractor’s Sexy’, which remains one of his go-to encore songs at his live shows.

The first hints at Chesney’s gear shift from the lovelorn ballads of Brooks and Strait to the tropical escapism of Jimmy Buffett emerged on 1999’s ‘How Forever Feels’. Shortly after the turn of the century, Chesney’s new mission statement was concretised in his 2002 quadruple-platinum album, No Shoes, No Shirt, No Problems.

From that point on, through his expansive discography and the high-octane live shows that he has become known for, Kenny Chesney has taken ownership of country music’s slow lane, celebrating the joys of island living and removing oneself from the stress of the rat-race.

It’s a philosophy that has been embraced as a cri-de-coeur for members of his loyal ‘No Shoes Nation’ fan club, with Chesney embodying the modern longing to break free from an accelerating pace of life. For many, this pinpoints the reason why his music feels more relevant than ever today.

Along with No Shoes, No Shirt, No Problems, Chesney’s 2004 project, When the Sun Goes Down, and 2005’s Be As You Are completed a trio of albums that showcased the various facets of his sound. From the rum-drenched, sandbar soundtracks (‘Guitars and Tiki Bars’, ‘When The Sun Goes Down’, ‘Big Star’), and the wistful odes to years gone by (‘I Go Back’, ‘Young’, ‘Live Those Songs’), to the intricate ballads often accompanied by nothing more than a simple acoustic guitar (‘Old Blue Chair’, ‘Be As You Are’, ‘Sherry’s Living In Paradise’, ‘There Goes My Life’).

It’s a recipe that Chesney honed through the remainder of the 2000s and 2010s, racking up a suite of uptempo smash-hits, such as ‘You and Tequila’, ‘Setting the World on Fire’, ‘All the Pretty Girls’, ‘American Kids’, ‘Get Along’ and, more recently, ‘Here and Now’.

While Chesney’s music is notable for its tropical nature, to focus only on this overlooks his unique ability to weave in heart-wrenching tales of love and loss (‘Don’t Blink’, ‘Hemingway’s Whiskey’, ‘Knowing You’), without every straying from his core credo, which is most lucidly expressed in the hook of ‘Happy Does’ (“Steal a slow dance in a rain storm/And a kiss from who you love/Laugh and live with a half-full cup/Yeah, happy is as happy does”).

That song featured on Chesney’s most recent album, Here and Now, which he released during the pandemic in 2020. It debuted at No. 1 and became the singer-songwriter's sixteenth Top 10 album.