Caribbean Cowboy

By Dave Herndon

updated 4:23 p.m. ET Sept. 20, 2005

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

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.

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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.”

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