A Pirate Looks At Fifty by Jimmy Buffett

How many of Jimmy Buffett’s Big Eight (now the Big Ten) could you name? A few weeks ago I could’ve gotten two for sure, maybe three, I’m no Parrothead.  When I thought of “Jimmy Buffett,” I thought of MW’s story of listening to his greatest hits on cassette on their way to family vacation, with his mom reaching over to frantically fast forward whenever “Why Don’t We Get Drunk and Screw” came around.

In Mile Marker Zero I loved the origin story of Jimmy Buffett: down on his luck in Nashville, goes to Miami for a gig, only to find either he or the club owner got the dates wrong.  Stuck, he calls his friend Jerry Jeff Walker, whose girlfriend suggests they take the unexpected week and go down to Key West.  When Jimmy Buffett sees the lifestyle there he knows he’s in the right place and never turns back.

The Margaritaville retirement community was profiled in The New Yorker.  How many of the singer-songwriters of the ’70s have a retirement community based on their worldview? John Prine? Kris Kristofferson? Only one. At the Berkshire Hathaway annual meeting they sold a Jimmy Buffett boat. The man is a phenomenon. Why?

On a warm spring morning driving from Chapel HIll to Wilmington, NC in a rented Ford Escape armed with Sirius Satellite XM, I put on Parrothead Radio.  They were playing a live concert from March 2001.  “Before 9/11,” I thought.  The contagious fun of this man came through, and the joy of the audience. It’s strange since, can you even really picture Jimmy Buffett?  You can picture what kind of shirt he wears.  

He’s in that kinda shirt on the cover of the mass market paperback of A Pirate Looks at Fifty. On a sunny beach obviously.  Behind him is an enormous Albatross seaplane, the Hemisphere II. 

This is a travel book, and a great one.  I’d rank it up there with Bruce Chatwin’s The Songlines, which it references a few times.  I bet more of A Pirate Looks at Fifty is true.  I saved this book to read on the beach in Malibu – perfect setting. The book, leisurely, describes a trip around the Caribbean Sea to commemorate his fiftieth birthday, with stops in Grand Cayman, Costa Rica, Cartagena, St. Barts.  A treasure map opens the book, you can follow the voyage.  Along the way, Buffett tells of his rise and his adventures.  He desired to be a Serious Southern Writer, but that wasn’t him.  As a boy he was struck by a parade at Mobile Mardi Gras of Folly chasing Death.  That was him.  Catholicism plays a bigger role than you may suspect, with St. Louis Cathedral in New Orleans his home church, but plenty of bad behavior to balance the ledger.  A friend at Auburn teaches him the D and C chords on a guitar. He busks on the corner of Chartres and Conti in New Orleans.

My talent came in working an audience.

Buffett begins the book with four hundred words summing up his life to present. An excerpt:

I signed a record deal, got married, moved to Nashville, had my guitars stolen, bought a Mercedes, worked at Billboard magazine, put out my first album, went broke, met Jerry Jeff Walker, wrecked the Mercedes, got divorced, and moved to Key West. I sang and worked on a fishing boat, went totally crazy, did a lot of dope, met the right girl, made another record, had a hit, bought a bought, and sailed away to the Caribbean.

Having brought us up to speed, he gets going. This is a memoir more of flying and fishing than of music. Buffett is a pilot, and recounts many adventures in the air, usually flying somewhere to fish or surf.

In looking back, I see there wasn’t that much difference between Jimi Hendrix playing “The Star-Spangled Banner at dawn at Woodstock and Jimmy Stewart playing Charles Lindbergh in “The Spirit of St. Louis.”

Memorable meals are described: cucumber and tomato sandwiches at the brassiere on the Trocadero in Paris for example.  And bars: Buck Forty Nine, New Orleans; Trade Winds, St. Augustine; The Hub Pub Club, Boone NC; Big Pine Inn; The Hangout, Gulf Shores; The Vapors, Biloxi; Le Select, St. Barts. 

Of a visit to paintings of Winslow Homer and Frederick Edward Church:

I can’t put the feeling into words; the closest I can come is to say that the sights and sounds of such things may enter the body through the senses but they find their way to the heart, and that is what art is really about.  

Buffett says:

Anyone bellying up to a bar with a few shots of tequila swimming around the bloodstream can tell a story. The challenge is to wake up the next day and carve through the hangover minefield and a million other excuses and be able to cohesively get it down on paper.

Mission accomplished.



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