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Kenny Chesney: Pirate vs.Poet

Kenny Chesney: Pirate vs.Poet

The chart topper may appear laid back, but there is intensity to spare when it comes to his music.

By Betsy Model

As fantasies go, the scene has got to be in the top three: warm beaches, lapping waves and an occasional ocean breeze; hammocks swing lazily between palm trees, boats bob offshore and afternoon thirst is quenched with cold cerveza, while evening requires rum-based cocktails to accompany a dinner of grilled fish caught just hours earlier. Here, flip-flops and tank tops suffice for formal wear.

Kenny Chesney

Kenny Chesney has sold more than a million tickets every single year of his last 11 tours. Photo by Craig ONeal/Wikipedia

Country music superstar Kenny Chesney not only loved the idea of the island life, he found a way to live it and, simultaneously, turn it into a “no shoes” lifestyle brand that has brought an entirely new generation of fans into a fold that’s part old-school Nashville, part Margaritaville and accented—a lot like that twist in your tequila sunrise—with a bit of Marley.

Kenny Chesney’s got a hell of a life –he’ll be the first to admit it –but he’ll also offer up a well-earned piece of advice: It’s a lot of work making life look easy. Nashville isn’t called “Music City” for nothing. In its own odd way, the town bears a striking resemblance to Los Angeles and New York, and while tons of folks migrate there to try and catch that one possible break that will lead to success, you could throw a cowboy boot into a crowd at The Basement or any of the other music venues that make the city what it is and never hit a Tennessee native. Kenny Chesney’s roots are different.

Tennessean, Born and Bred

Born in Knoxville, Chesney grew up playing high school sports in nearby Corryton and earned a degree in advertising from East Tennessee State. Both athletic and social by nature, he could have pursued a career in business, including the behind-the-scenes business world of Nashville’s continually evolving music world. However, Chesney was given a guitar while in high school, and while teaching himself to play became hooked on not just the playing of the instrument but the playing with words that comes with writing lyrics.

Pursuing a secure and stable career in business would have been, in theory, easy for him—the man has a sharp mind and remarkable writing skills—but he let his youthful soul decide and, he says, rarely looks back.

“I started playing for tips and burritos in college, and I liked it!” Chesney said. “I’d always loved songs on the radio, and I figured, ‘Why not?’ since the time to chase a crazy dream is when you’re young. So the day the Gulf War started, I got in my little Toyota pick-up and headed for Nashville.”
Flash-forward 25 years and its obvious that Chesney picked the right road to follow. The man’s sold more than 30 million albums, has had an absurd 26 number-one singles on the charts, and 39 of his songs have hit Top 10 status.

Kenny Chesney

Kenny Chesney at a concert in Madison Square Garden, 2007. Photo by Lawrence Fung/Wikipedia


Chart-topping singles make an artist popular with his label, his accountant and the IRS. But before them comes the fans, and their embrace of Chesney and his unique music mix of mostly upbeat, “damn, ain’t life fun” tunes hasn’t gone unnoticed by the industry. Chesney has won four Country Music Association Entertainer of the Year awards, four consecutive American Country Music Entertainer of the Year awards, and judging from the sheer numbers it’s obvious he’s doing something right when he’s on tour.

Chesney, who calls being on stage “the best two hours of my life every day,” is, at 47, selling out concert venues wherever he goes, and we’re not talking small, intimate venues that seat a couple hundred. He’s sold more than a million tickets every single year of his last 11 tours. That is a whole different version of “being on the road” than one suspects Chesney imagined when initially heading to Nashville.

By the time the man and the city first met in 1990, Chesney had already cut his own self-released album a few years earlier while still in college, but once in Nashville, the former high school athlete was playing ball on new turf and against a lot of other players. He had his degree to fall back on but was prepared to pay the dues that most struggling musicians need to even stay in the game.

In Nashville that can often mean minimum-wage day gigs that allow for nighttime playing in the city’s honkytonks and bars. Chesney became a regular act at The Turf, a now-defunct bar in the city, and did what he needed to gain exposure and get that first label signing.

“I parked cars, I played for tips on Lower Broadway, and, when I had a few songs, I got lucky and got a publishing deal at Acuff-Rose, the home of Hank Williams’ publishing. Now I was in the business! Why would I want to go home? And I kept getting enough breaks to stay.”

Chesney’s lucky breaks continued and, in an industry where artists can sometimes go four or five years between albums and enough quality material to make them happen, Chesney developed a reputation as not only a near-machine when it came to creating material and moving it out to the public, but he’d found a groove in creating music that a whole new generation of music buyers—a younger, slightly friskier audience—was obviously relating to.

Chesney was pushing out new titles every 12 to 18 months, and the album titles began to say it all. He released titles such as No Shoes, No Shirt, No Problems; All I Want for Christmas is a Real Good Tan; When the Sun Goes Down; Be As You Are; The Road and the Radio and Just Who I am: Poets & Pirates. These albums pointed clearly where Chesney was headed, both commercially and personally.

Island Life Beckons

While the fans and concert goers were lapping up the songs and the tour tickets, Chesney was finding himself balancing his success by spending at least part of every year among the lapping waves of the U.S. Virgin Islands.

He’d purchased a home there, and Chesney himself has credited his time “in a slower environment” with both a change in perspective and a change in his music. The steel drums that began showing up in some of the songs was one indicator, but so was the growing dichotomy in Chesney’s demeanor and persona that fans seemed to relate to; cowboy boots and hats stayed in place but were often paired with tank tops, puka shell necklaces and ripped-sleeve t-shirts that felt more Margaritaville than Nashville.

On display was more than Chesney’s cut physique. Although the man rarely misses a daily gym workout, even while touring, the videos that are such a huge marketing push behind album and individual song releases began featuring a Chesney that was not only physically sound but perhaps. . . happier?

When asked about his move to the islands and the gradual shift in his music, Chesney acknowledges that it was quite a switch but not one that was turned on/off quickly, or that was really all that radical from what he began to see he wanted in his life when off the road and off the stage.

“It’s not like you throw a switch and decide to become a beach bum. I think it’s something in your soul. When I was a young boy, my mother would take us to the beach for vacation and the ocean felt right to me. Later, I went to the Virgin Islands and made the ‘How Forever Feels’ video. I spent some time there and really liked the way the living felt—people were chilled out and they enjoyed life. No one was in a rush. And you had the water. You could spend days just watching the sun move across the sky.”

Of Pirates and Poets

Fans began seeing a different side of Chesney, and while the slick, carefully orchestrated videos that featured perfect lighting, perfect women and frames perfectly timed to beat and lyric were still part of the gig, they were now interspersed with others that were wonderfully, perfectly imperfect.
Almost as if shot by frat boys on spring break, this new song-to-video style saw Chesney hanging with friends—island friends of all sizes, shapes, colors and ages—being nothing short of good-time goofy. Sunburned backs got slapped, beers got lifted and not every move in the waves, on the boat or in the conga line were brilliantly choreographed. And did that ever click with Chesney’s fans.
Whether an intentional product branding or not, Chesney now was a brand and in spite of the good ol’ island boy persona, he had the brains to know it. Not unlike Jimmy Buffet’s loyal Parrot Heads, Chesney had created a movement that became tagged with part of his 2002 album title, No Shoes, No Shirt, No Problems.

Soon came the member-driven online and tour community called No Shoes Nation, supported, at least subconsciously, by all of the shoeless frolicking and good times that were to be had per Chesney’s videos and album covers and fortified by a new online surf-vibe radio station called No Shoes Radio (noshoesradio.com).

The No Shoes Nation logo features a skull and crossbones straight out of pirate lore; all that’s missing is a chest of booty and a bottle of rum. The Caribbean is famous for its rum, as well as its wealth of bikini-clad booty, but Chesney was savvy enough to go for the rum. He had spent the last decade being courted by folks who wanted to associate his brand (there’s that word again) with their brand, and there was no shortage of distillers and libation companies that realized Chesney could be the perfect hawker of any drink even remotely associated with beaches, babes, boats and good times.
The problem is Chesney knows his spirits and didn’t see, or taste, anything that really knocked him out. So, after a number of years and in tandem with a Caribbean-based distillery for authenticity and a hand-picked Master Distiller, Chesney announced his own brand called Blue Chair Bay.

“Blue Chair Bay happened because I’d been courted by a couple of spirit companies who wanted to do a rum with me, but it never felt like they understood that if I was going to do a rum it needed to be something I actually wanted to drink"

“Blue Chair Bay happened because I’d been courted by a couple of spirit companies who wanted to do a rum with me, but it never felt like they understood that if I was going to do a rum it needed to be something I actually wanted to drink.”


The decision, Chesney explains, was as much about evoking a spirit as simply creating any old, uh, spirit. “Blue Chair Bay happened because I’d been courted by a couple of spirit companies who wanted to do a rum with me, but it never felt like they understood that if I was going to do a rum it needed to be something I actually wanted to drink. The more people talked to us, the more I realized that if I wanted to put my name on a rum I would serve my friends, I was probably going to have to do it myself.

Authenticity was very important to me. We went to the oldest distiller in the islands—their factory is a few hundred feet from the ocean—and we brought in Mike Booth, a man who’s incredibly well-respected in the industry, to help distill the exact flavor I wanted.

To me, rum is one of those spirits that’s about how you spend your time, how you enjoy it. It’s to relax, it’s to have fun, and Mike got that. With Coconut and Coconut Spiced the initial flavors, he found a way to balance the rum with the other essences to create a blend that was balanced and that tasted like a day on a boat might feel. And the silver? That has medaled in every competition we’ve ever entered it in.”

Free Spirited, With 

Country musicians are famous for featuring alcohol and the consumption of same in their lyrics, often in conjunction with getting over a lost love, a lost truck or a lost dog, but while many of Chesney’s song lyrics of the last 15 years are no exception, most of them have been a bit more playful, a bit more “don’t worry, be happy” than about drowning unending sorrows.

Chesney acknowledges that his 2010 album, Hemingway’s Whiskey, was a bit darker, but also stands by its lyrics and what he says really goes back to pirates—and cowboys—being poets deep down.
“’Hemingway’s Whiskey’ is a Guy Clark song that evokes the nobility of being a man but also the ability to be a free spirit. ‘Sail away, sail away/Three sheets to the wind/Live hard, die hard/This one’s for him.’—what is more manly than that? More poetic? And in a way, more of a pirate’s swagger?
Or the sadness of ‘You And Tequila’—the knowing better and the fighting to fight it, but knowing there’s always that one thing you can’t quit. It’s a whole other kind of heroism, really. That album (Hemingway’s Whiskey) was really about the power of songs to distill life. I think it’s easy with the singles to miss the meat on the records. I am all about having fun and about celebrating life but, in the end, it’s those album cuts that haunt you, that really speak to who we are at our core.
Those are a lot of words to explain an album that I think was about so much more than even the songs! It was about digging into the human condition without losing your sense of truth. Some of life is hard, some of life’s silly, but in the end, celebrate every last moment.”

It would be easy to pigeonhole Chesney, yet while much of his riffing about life seems to focus on the celebratory and good times he can, much like his beloved ocean, turn tide to focus on business with an intensity that far more resembles a CEO shark and far less a poet or philosopher.

Nothing brings this switch about faster than suggesting Chesney’s life is one big beach of late nights and happy bachelorhood or that the most important decision of a typical day could be, oh, what SPF to apply. This is a big misperception, he says—and perhaps it’s also a pet peeve—and one that he wants to put straight to anyone who thinks that making life look easy is easy.

“Maybe because of the singles and the videos people think that, and it’s ironic because it takes a whole lot of focus and energy to do this. You talk about staying up all night, hanging out, going to the beach, but I’m up at 5 a.m. and on my way to the gym! I sit in business meetings, video editing sessions and recording studios, writing appointments. I have a couple hundred people who depend directly on me for their living. It’s not all carefree and easy-going because I take those people, their lives and their families very seriously. I also [give the] No Shoes Nation the best show every time I go out, and that requires taking care of myself.

Maybe that’s not sexy or the fantasy, but that’s what it is. It’s about respecting all the people in my life. We all have a great time doing this because we love the road and making music, finding our way around the world like gypsies. But it’s something we also take pretty seriously. I’ve often said we’re a lot like a baseball team: six months on, six months off. And those six months off? You’re getting ready for the next season.”

Still, Chesney can’t seem to help letting the philosopher peek out one last time, as if striving for a balance only he can see. “Don’t lose sight of what matters to you—your friends, your family, your faith. It’s so easy to get bogged down in life or work or whatever, [that] you miss the opportunity to have fun.

“Life is what you commit to. What you put in is what you get out.”


Award-winning writer Betsy Model lives in Santa Fe, New Mexico.

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