updated 9/20/2005 4:23:19 PM ET 2005-09-20T20:23:19

Country music’s hottest artist trades his sexy tractor for a blue chair on the beach and scores a number-one album.

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A snowy blast of winter air blows a slight, slacker-looking guy into a television studio dressing room. He strips off a tired old shirt from Woody’s Seafood Saloon in Cruz Bay, St. John, and replaces it with a bright tie-dyed tee. Baggies give way to jeans, a stocking cap comes off and a palm-leaf cowboy hat goes on — and that quickly, the island bum transforms into the Nashville superstar.

Such is the ease with which Kenny Chesney bridges the seemingly apples-to-oranges styles of the Caribbean and mainstream country & western.

As he warms up before his live prime-time Saturday-night special on Country Music Television, it occurs to Chesney that the show will have particular meaning to a certain slice of the millions expected to tune in. “I know all my friends down in St. John are going to be havin’ a party and watching, ‘cause they know all the songs are about them. And I’m sure Foxy’s gonna be watchin’,” he says, giving a nod to legendary bar owner/impresario Foxy Callwood from Jost Van Dyke in the British Virgin Islands.

Onstage, the mood set by the backdrop of a magenta sunset framed by palm trees, Chesney introduces cuts from his new album Be As You Are (Songs From an Old Blue Chair). The songs are full of fond references to piña coladas, tiki bars and the shaggy appeal of island life as lived by his friends — expats, boaties and barkeepers, mainly.

Slideshow: Caribbean way of life Such tunes, some with calypso steel drums and reggae-lite rhythms, have been a growing component of Chesney’s repertoire for the last few years. This album, though, represents a full-blown case of island fever. His trademark hook-heavy hot-country sound is shelved to make room for a melodic, gently twangy brand of balladry that goes down easy as a sunset. Chesney auditioned his own rough mixes by listening to them on his boat to make sure they had just the right feeling.

The album hit number one on the Billboard 200 its first week — the latest winner in a rampant Caribbean-Country trend.

Songs about escaping to the islands — notably, “Some Beach” by Blake Shelton and Alan Jackson’s “It’s Five O’Clock Somewhere” — were all the flavor on country radio this winter. The mayor of Margaritaville himself,  Jimmy Buffett, has been sailing these profitable trade winds, chiming in on Jackson’s hit and clocking the first number-one album of his long career, License to Chill, by collaborating with Nashville’s elite — including Clint Black, Toby Keith, George Strait, Martina McBride and, of course, Kenny Chesney, the reigning Country Music Association Entertainer of the Year.

“Jimmy always had a country soul to him,” says Chesney over lunch the day after his CMT show. “‘Come Monday’ was a country song, and ‘A Pirate Looks at 40’ is a story song like most country songs are stories. Jimmy moved into it naturally, and I was proud to be a part of his record.”

But Chesney is eager to put a bit of distance between himself and the pack.  He doesn’t want to be taken for an opportunistic Parrothead wannabe  — he’s not a tourist, he’s a local now. “I don’t want people to think this is a weekend with Jimmy Buffett,” he says.

Yes, he’s sensitive to the issue of influence when it comes to Buffett. “We have a lot in common in the way we live our lives,” says Chesney, “and when I listen to his earlier records I see he was a dreamer, too. But as much as I love him, he’s got nothing to do with my new album.

“Look, I realize ultimately people are going to compare this record to his,” Chesney continues, “but it’s so much about me and my feelings and a life-changing period I’ve been through. I wrote these songs about people I know with kind hearts and deep souls. I’m setting their lives to music. I’m not just listening to ‘Margaritaville’ on a boat for a weekend. This is not a case of trying to steal style points.”

So does that mean we’re not going to see a chain of Kennyville tiki bars opening up any time soon? 

The idea has been floated. “I never say never,” says Chesney, “but I’m not ready to commercialize myself that much just yet. That would take a little bit of the heart out of it for me.”

Chesney’s Caribbean journey began during vacations with his former fiancée to Grand Cayman, which is a place now and forever tainted by those painful associations. It inspired a song called “I Can’t Go There” from the 2002 album No Shoes, No Shirt, No Problems. And it was his quest for a fresh place in the sun that brought him to St. John in the U.S. Virgins.

“I was running from insecurities and a love affair,” he says, “and chasing something — peace or resolve. And one reason I fit in on St. John is that I saw a lot of commonality. There are a lot of people down there in the same boat, emotionally.” 

Same boat, perhaps, but they probably don’t commute to the islands by Lear jet. The folks who populate Chesney’s Caribbean songs include dropouts living off the tourist trade, like the harborside shopgirl from “Boston” and the bartending subject of “Sherry’s Living in Paradise.”

Chesney first visited St. John with his father for a brief vacation, then took his whole band down for a month, making friends with the people who, he says, showed him a different way to live. “There’s beaches all over the Caribbean,” he says, “but the people there made me feel at home, made me feel like a local.”

Though his island dream house is still in the dreaming stage, as often as he can Chesney occupies a hillside four-bedroom Mediterranean-style villa with open walls and a “killer view” of the Virgin Islands. The most important piece of furniture is the subject of a song he says is his most personal, “Old Blue Chair.” In case you missed it on his last album (When the Sun Goes Down, the CMA Album of the Year), the chair shows up in the subtitle and in the first track of Be As You Are (Songs From an Old Blue Chair), and again at the end, with a reprise version recorded seaside last summer in the BVIs complete with the sounds of sloshing surf. He wrote the song after a night of partying with houseguest Peyton Manning, star quarterback of the Indianapolis Colts.

I’ve read a lot of books, wrote a few songs

Looked at my life, where it’s goin’, where it’s gone

I’ve seen the world through a bus windshield, but nothin’ compares

To the way that I see it

When I sit in that old blue chair

“One New Year’s Eve when I was in my soul-searching period,” recalls Chesney, “I went out and sat in that chair with a big drink between my legs. I looked up at the infinite stars and fell asleep — or passed out, whatever you want to call it. What woke me was the sun coming up over Tortola. It had rained a lot, and the mosquitoes were horrible; I must’ve had 200 bites all over my body. Right then I decided I was going to make myself happy and move on and put my heart and soul into my music and into being a better person.

“Is that what you call an epiphany?” he wonders aloud.

No, that’s what you call a hangover; it’s only an epiphany when you act on it and it becomes a turning point. Which he did. Chesney rededicated himself to competing in the bare-knuckle brawl that is the Nashville music industry, but tempered his ambitions with an accepting perspective learned from his Virgin Island buds. He took inspiration from a friend named Ben (the subject of the song “Island Boy”), who “left Maine, sold everything he had, looked at a spot on the map and went to it.” From that, Chesney learned that while it’s risky to follow your bliss, doing so can take you to places where you really belong.

“Now I let my heart take me where it wants to go,” he says, echoing a line from the chorus of “Soul of a Sailor.” “That’s the essence of the islands and why I love it.”

Ben is now the captain of Chesney’s new boat, a 60-foot Sea Ray. Together they cruise the islands, stopping at spots like Ivan’s Stress-Free Bar on Jost Van Dyke. It’s one of those places where you can just walk up and make your own drinks, pitch a tent and stay for a few days, a week, a month.

“When I think of the Caribbean, Ivan’s is where my mind goes,” Chesney says. “It’s got a great vibe. Ivan is a kind, warm person from the West Indies, in his 60s. He’s a musician and he loves musicians. I’ve learned to look at the world differently there, how to pace my life. My view is through a tour-bus window; his view is of the tide coming in and going out.”

Ivan’s is one of several such bars mentioned in Chesney’s songs.

“There’s an unseen magic in those places that can be life-changing, and I’m living proof of it,” he says. “You can lose yourself and find yourself and reinvent yourself.”

Such a true believer is Chesney in the transforming power of island vibes that he feels compelled to share what he’s discovered not only with his crew, whom he transports down there en masse at the end of each long, grueling tour (he sold 1.2 million tickets last year, more than anyone but Prince), but also with his fans. “I want to bottle up all of it and take it on the road,” he says.

That would explain Marley, the 265-pound blue marlin he caught off the Northern Drop in the BVIs that goes on tour (in a custom case that cost 10 grand) and sits at the side of the stage as a talisman for the team. “In my live show people really connect with the whole vibe,” says Chesney, who used to use Bob Marley’s “Three Little Birds” as his intro music. “It’s not just a song on the radio.”

An inevitable consequence of his Caribbean fixation is that Chesney fans are increasingly taking vacations to the Virgin Islands. “They’re following in droves,” he says. “It’s double-edged. I want them to buy into the lifestyle, but there used to be a time I could dance on the bar and howl at the moon. There are too many cameras now. Thank God I got a boat and there’s a lot of little islands.”

He still likes to howl, though, at the drop of his old straw hat. “After I played the University of Tennessee with Kid Rock two summers ago, the two of us got on my bus, stopped at Krystal for 20 burgers, went to the airport, got on my plane, flew to the Virgin Islands, got on my boat and went to the BVIs. The night after we played for 65,000 people at UT we played four hours for 60 or 100 people at Foxy’s. We played all his stuff, all my stuff and every Marley song we knew.”

For all the carrying-on and the spontaneous tiki bar gigs, the islands are primarily a place for Chesney to decompress, get away from music for a while and read. In the grand tradition of Caribbean literature, he says Old Man and the Sea is his favorite Hemmingway book (“reminds me of my grandfather”), and it’s recently prompted him to catch up on To Have and Have Not.

But there comes a time during the long vacations when he can’t resist picking up the guitar. Be As You Are is his first singer-songwriter album, a scrapbook of tunes that he says were never even meant to be recorded, much less released as a theme album. However, one of the fruits of achieving success on Nashville’s terms by producing monster hits like “She Thinks My Tractor’s Sexy” is that you eventually get to share the stuff that’s a bit closer to your heart, more about where you’re really coming from.

“It used to be my home away from home,” says the Tennessee native of his Virgin Islands getaway, “but now it’s my home more than anyplace else. Without the island lifestyle I wouldn’t have the energy or the inspiration to accomplish what I have. Being able to shift gears has given me clarity and focus. The people, the boat, the bars, the fishermen, the music, the blue chair, the rum — everything helped make that happen.”

On that tidy note, the luncheon interview concludes and Chesney cracks open his fortune cookie: “A much-needed vacation will bring a great deal of enjoyment.” But he already knew that.

Caribbean Travel & Life is the magazine for anyone in search of the perfect tropical getaway. Each issue presents expert insider’s advice on where to find the Caribbean’s best beaches and attractions, its finest resorts and spas, liveliest beach bars and activities, and its friendliest people.


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