A Pirate Looks at 60

Jimmy Buffett’s midlife crises.

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Jimmy Buffett

Jimmy Buffett turned 60 this past Dec. 25, a day he undoubtedly spent in a lower latitude, in a meditative frame of mind, in close proximity to a tankard of Captain Morgan. At least that was the case with birthday number 50, which, as recounted in his autobiography A Pirate Looks At Fifty (1998), Buffett celebrated by piloting his private jet from the Cayman Islands to Costa Rica to Colombia and drinking copiously, while contemplating “spirituality” and his goals going forward: “Learn celestial navigation,” “Swim with dolphins,” “Start therapy.” Anyone who has heard a Jimmy Buffett record will know that therapy is totally unnecessary. Buffett has been writing and singing confessional songs for three decades, but he’s never shown the slightest sign of discontentment—shrugging away the world’s sadness, and his own indulgences, with an amused “I know it’s all my fault” while oozing over to the bar for another round.

And who can blame him? Buffett is one of the music business’ singular success stories. He has parlayed an unlikely subject—getting shitfaced while cruising the Gulf Coast in your power boat, basically—into a multimillion-dollar industry, a perennial place on Forbes list of highest-grossing entertainers, and the most passionate concert audience this side of the Deadheads. (He also has written a couple of New York Times best sellers, operates a chain of seaside bars, and has his own seaplane airport, Lone Palm. Take that, Mick Jagger.) Buffett has done all this without altering his music one iota—indeed, without any evident effort at all. He’s a bard of hedonism, the sunbaked, can’t-be-bothered-to-stir-from-this-beach-chair variety. His songs are nudged along by lazy rhythms and gentle country-rock acoustic strumming, and accented by the rounded ping of steel drums—the universal sonic signifier of Caribbean languor. He takes the stage of sold-out arenas and baseball stadiums in the same T-shirt and baggy beach shorts that he wears aboard ship, and can’t even bring himself to put on a pair of shoes. Does he even own shoes?

I learned about the Buffett dress code the hard way, when I turned up wearing street clothes at a Madison Square Garden concert on a chilly evening last September. I had heard tales of Buffett’s rabid fans, the Parrotheads, and was prepared for an onslaught of Hawaiian shirts. But that was just the beginning of the Club Med-wear. I came up the subway stairs to find a phalanx of men in their 40s striding down Seventh Avenue in plastic leis and grass skirts. Headgear ranged from Carmen Miranda-style fruit baskets to baseball caps topped with foam shark fins. Waiting in line at the Garden turnstiles, I stood next to a fellow with a papier-mâché outboard motor belted around his waist.

Buffett sells a lot of records—his latest album, Take the Weather With You, topped the country charts when it was released last October. But it’s touring that has made his fortune, and to really understand Buffett, you have to spend a couple of hours in a room with 15,000 people singing along with every lyric while batting giant inflatable sharks overhead. “Parrotheads are known, to, um … begin their preparations early,” Buffett said to cheers shortly after taking the stage, and indeed, much of the audience was unmistakably blotto well before the first steel drum sounded. Buffett sang a stately new song, “Here We Are,” which marvels at the enduring, well-soused fellowship of Parrotheads: “Who would have thought this game, this flame would still be burning?/ Who would have guessed that all these blenders would still be churning? … Here we are, with our fins up and our feathers flashing/ Here we are, with our coconut shell brassieres, chanting.” Video screens flanking the stage played footage of the Parrotheads’ famous parking lot antics. It looked like a giant frat party—a Girls Gone Wild video, with the part of the 19-year-old co-eds played by paunchy middle-aged men—but for Buffett, Parrotheads are heroic nonconformists, and their bacchanals have vague spiritual overtones. In “Here We Are” he sings: “Here we are, all the black sheep family outcast and a freak or two. … We’re the offbeat Uncle Freds who spill their wine on you. … We’re the dreamy Deadheads who just like us and Dave Matthews.”

Parrotheads are as devoted as Deadheads and Dave Matthews fans—doubtless many in attendance at the Garden had followed Buffett up the coast in their minivans. But musically, Buffett has nothing in common with jam bands. He fronts a slick 12-piece group, the Coral Reefers, and they breeze through the same songs, in the same way, note for note, night upon night, year after year. Buffett has a knack for ingratiating singalong melodies and sharply detailed lyrics, and he’s ruthlessly single-minded. Few pop stars have carved out so distinct a theme and stuck to it unwaveringly for so long, with such fearless zeal for bad puns: “Last Mango in Paris,” “Changes in Latitudes, Changes in Attitudes,” “Off To See the Lizard,” “Floridays,” “The Weather Is Here, Wish You Were Beautiful,” “Jamaica Mistaica,” “License To Chill.”

Buffett is not the first American pop singer to sell tropical fantasies. The tradition stretches from Tin Pan Alley’s Hawaiian ballads of the 1910s, to Bing Crosby’s and Elvis Presley’s revivals of the theme, to ’50s-’60s exotica and Don Ho, on down through Buffett to country beach bum Kenny Chesney. But where the other performers have mystified the islands, Buffett is unsentimental and journalistic. In admirable detail, his songs depict tourist traps, where the locals exist only to pour your drinks and cheeseburgers in paradise are on the menu. Buffett is unambivalent about this ugly Americanism—he’s all for it. Buffett’s music is often hideously tacky, objectionable on both moral and aesthetic grounds, but you have to give him credit for capturing a milieu and a mindset. He’ll never get the respect given to his generation’s more celebrated troubadours, but he may prove more valuable to future social historians as a chronicler of late-20th-century American folkways. Go to Bob Dylan and Paul Simon for poetry and pretty tunes, but if you want to know how baby boomers ate, drank, and screwed on vacation, reach for Boats, Beaches, Bars, and Ballads.

By all accounts, Buffett lives the life he sings about. For his fans, most of whom aren’t multimillionaires with large pleasure craft, the experience is vicarious: The closest many will come to a Caribbean lagoon is a kiddie pool in the parking lot of a Jimmy Buffett concert. Yet Buffett’s songs are not so much about an escape to a place as a flight from time. His true theme is the Me Generation midlife crisis. Buffett’s tunes are sunny and easygoing, but they have a desperate undercurrent: the hopeless hope that the party need never end, that you can, as one song put it, “grow older but not up,” remaining reckless and responsibility-free deep into adulthood.

Two decades ago, in “Pirate Looks at Forty,” Buffett cast his plight in mock-historical terms: “Yes I am a pirate, two hundred years too late/ The cannons don’t thunder, there’s nothing to plunder/ I’m an over-40 victim of fate.” More recently, in the Parrothead anthem “Here We Are,” Buffett put it in starker terms. “It’s the child in us we really value,” Buffett sings. That message has proven to be very good for business, and there’s no reason to doubt Buffett’s sincerity. Somewhere right now—probably a very warm, palmy place—the pirate is looking at 60 in the same way that he will look at 70, and, if his liver holds up, 80. Through a boozy haze, with the blue ocean gleaming on the horizon just over the rim of a shot glass, it looks awful lot like 18.