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Impersonating a pirate was part of his marketing plan. Born on Christmas Day, 1946, in Pascagoula, Miss., Buffett was raised in Mobile, Ala., where his father worked in the shipyard. He was an altar boy who busted loose, discovering girls and guitars at Pearl River Junior College in Poplarville, Miss., playing acid rock in the clubs of New Orleans, moving to Nashville and working for Billboard, and failing in his first bid for folkie stardom (his debut album stiffed, and his second was put on the shelf). In 1971 he fled Tennessee and a bad first marriage and wound up at the end of the road in Key West, then a lazy outpost for shrimpers, smugglers, gays and cosmic cowboys like singer Jerry Jeff Walker and novelist Tom McGuane, who ended up married to Buffett's sister Laurie.
"Back then I was havin' such a good time bein' me," Buffett says. "I was like a flower in bloom." He wrote a satchelful of sparkling, finely detailed songs about life in the Keys and toured constantly, attracting a following and then a new record deal. Promoting himself, he liked to imply that he had smuggled marijuana to make ends meet. When stardom hit, Rolling Stone repeated the old tales in a 1979 cover story, and Buffett was detained by the authorities in St. Barts, where he was then living. "Me and my big mouth," he says. "I had never been a dope dealer; I was just hangin' in the bars, tryin' to be cool."
The legend was sealed by A Pirate Looks at Forty, a mournful 1974 ballad that is still a concert highlight. When its narrator, a pirate born "200 years too late," offers up a confession--"I've done a bit of smugglin'/ I've run my share of grass/ I made enough money to buy Miami but I pissed it away so fast"--Buffett's fans assumed he was singing about himself. In fact, he wrote the song about one of his disreputable friends. "I was never the damn pirate," says Buffett.
But he was the Prince of Key West. One night in 1971, Buffett was drinking, singing and passing the hat in the Chart Room bar when he met a radiant honey blond named Jane Slagsvol, who'd come to town for spring break from the University of South Carolina. The next night he saw her again, "wearing a tight, long pink dress that made a lasting impression on me." Jane moved in with Buffett and never did get back to school. They were married in 1977--the year Margaritaville hit--at an all-night Aspen blowout (the wedding band was the Eagles). But after five more years among the rock aristocracy, Jane needed a change. "I'd been with Jimmy since I was child, through the craziest times, and I didn't have a clue who I was. So I left. I got sober." The couple reunited in 1991, and have been together since.
Buffett partied longer than his wife did, but gave up drugs and tapered off his drinking when, he says, "the hangovers started to feel like surgical recoveries." After Jane left, he retreated to Key West, wrote some fine, broken-hearted songs (and some mediocre, jolly ones) and kept touring, though his audiences were getting older and sometimes smaller. When radio stations wouldn't play his new records, he figured his career was winding down and set about creating an alternative revenue stream. He and a friend opened a T-shirt shop in 1984 and expanded it into the first Margaritaville Cafe.