Kenny Chesney: Playboy Interview

There’s an old joke that goes like this: What happens when you play a country song backward? You get your wife back, your dog back and your truck back.

Country has evolved a lot since that joke was first told. The latest star to modernize the music is Kenny Chesney, a self-described “hillbilly rock star” from Tennessee with nitro-powered songs about antic times and warm beaches. If you play a Chesney song backward, you come home from the islands, sober up and feel as blue as the water off St. John. In Chesney’s music, problems are solved with a nostalgic memory, thoughts of family, an old rock song on the radio or, especially, a tropical vacation. Country music began in the South, but Chesney has taken it even farther south, down near the equator.

He has won country music’s entertainer-of-the-year title eight times and sold more than 30 million records. But he’s most distinguished by his concert success: In each of the past seven summers he has sold more than a million tickets, playing shows to as many as 60,000 people at once. No musician has sold more concert tickets in the 21st century.

“He is not only the biggest country star since Garth Brooks,” the San Francisco Chronicle declared, “but he is also the biggest country star ever.” Chesney’s renown was mostly limited to country fans until May 9, 2005, when he married actress Renée Zellweger. For Chesney it was the unlikely fulfillment of a fantasy: Years before, after seeing Zellweger in Jerry Maguire, he had written a song called “You Had Me From Hello,” inspired by her signature line in the film. But only four months after the wedding the couple announced they were seeking an annulment. Zellweger’s petition cited “fraud” as the reason, which led to a flood of tabloid rumors, including one that Chesney is gay.

His musical success did not come quickly. Born in Knoxville, Tennessee to a hairstylist who divorced Chesney’s father shortly after Kenny was born, Chesney was a B-list star in Nashville, the kind of singer who might face a lifetime of playing county fairs. He had six top 10 hits between his 1993 debut and 1998, but none was what Nashville calls a “career song,” a distinctive and unforgettable signature track.

Even the turnaround happened slowly. He had consecutive number one hit songs—including “You Had Me From Hello”—and in 2002 released No Shoes, No Shirt, No Problems. The album felt as if it had been recorded by a beach bum—it was relaxed, tan, refreshed. In place of country’s traditional steel guitars and fiddles, Chesney used tropical steel drums and congas. He transformed himself into a “voice of sheer contentment,” The New York Times explained. No Shoes went to number one on the pop album chart and sold more than 4 million copies, as did its successor, When the Sun Goes Down.

His latest album, Lucky Old Sun, addresses his relationship with Zellweger, describing his time in what he called “a pretty rough place.” The arrangements are unusually sparse, the singing subtle, and “Way Down Here” may be the finest song of his career, mixing gentle resignation with his usual themes of island life and alcohol.

“Our interview started a little after noon, at a renovated boathouse that is part of Chesney’s 20-acre estate on the Cumberland River outside Nashville,” reports Playboy Contributing Editor Rob Tannenbaum. “He spent much of the conversation laughing, even—or maybe especially—when we were discussing the misery of his fleeting relationship with Zellweger. ‘This is the longest interview I’ve ever done in my life,’ he said as the sky began to darken, but he never flinched from a question. We discussed the annulment, his premature baldness, his reputation as a ladies’ man and his friendship with Peyton Manning—all with amazing humor. No one can accuse Chesney of taking himself too seriously.”