A Pirate Looks at Fifty Paperback - 2000

Time on the Water

My Life
(In Four Hundred Words or Less)

When I was growing up in Alabama, the beginning of the new school year was a bad time. It meant the end of summer, which is my season. I packed away my shorts and T-shirts, put on socks, shoes, and my parochial--school uniform, and dragged my ass to class. To make matters worse, the first thing the nuns would make us all do on the first day back was to write about what we had done that summer. Having to recall it all while sitting in the antiseptic atmosphere of a classroom was like staring at the goodies in a bakery window with no money in your pocket. However, the bright side to the ordeal was that it reminded me of what lay ahead the next summer, and I carried those longings through the winter and spring until the last bell of the school year rang and I charged back to the beach. I don't know why the idea of trying to put fifty years of living into the same format occurred to me, but it did, and since I am way too familiar with the format, here it is. In four hundred words or less, this is what has happened from early adolescence until now.

I broke out of the grip of Catholicism and made it through adolescence without killing myself in a car. I flunked out of college. I learned to play the guitar, lived on the beach, lived in the French Quarter, finally got laid, and didn't go to Vietnam. I got back into school, started a band, got a job on Bourbon Street, graduated from college, flunked my draft physical, broke up my band, and went out on the road solo. 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 boat, and sailed away to the Caribbean.

I started another band, worked the road, had my second and last hit, bought a house in Aspen, started spending summers in New England, got married, broke my leg three times in one year, had a baby girl, made more records, bought a bigger boat, and sailed away to St. Barts.
I got separated from the right girl, sold the boat, sold the house in Aspen, moved back to Key West, worked the road, and made more records. I rented an apartment in Paris, went to Brazil for Carnival, learned to fly, went into therapy, quit doing dope, bought my first seaplane, flew all over the Caribbean, almost got a second divorce, moved to Malibu for more therapy, and got back with the right girl.

I worked the road, moved back to Nashville, took off in an F-14 from an aircraft carrier, bought a summer home on Long Island, had another baby girl. I found the perfect seaplane and moved back to Florida. Cameron Marley joined me in the house of women. I built a home on Long Island, crashed the perfect seaplane in Nantucket, lived through it thanks to Navy training, tried to slow down a little, woke up one morning and I was looking at fifty, trying to figure out what comes next.

That might be all some of you want to hear, but for those who want to read a little more, continue on, for though I got most of it all into four hundred words, there is a lot more meat on the bone.

Time on the Water

We sailed from the port of indecision
Young and wild with oh so much to learn
The days turned into years
As we tried to fool our fears
But to the port of indecision I returned
--"Under the Lone Palm"

I wasn't born in a trunk, I was born in a suitcase. But a trunk is where I've kept the scraps of my life for the past fifty years. My many attempts to begin a journal have all fizzled out after a few pages of notes. I have a considerable collection of notebooks, cocktail napkins, memo pads, legal tablets, sparsely filled binders, and mildew-spotted pages that sit in a cedar-lined steamer trunk in my basement on Long Island.

Almost five years ago, when I had the harebrained idea of doing a musical version of my friend Herman Wouk's Don't Stop the Carnival, Herman would send me pages of thoughts on the matter from his journal. He had kept a daily journal since 1946. To say the least, I was quite impressed. I envy those who have the discipline to keep a chronological record of events. I do not.

My plan has always been to keep adding to that mess in the trunk and, if I make it to my eighties and am still functioning in the brain-cell department, to retire to a tropical island, buy an old beach house, hire several lovely native girls as assistants, ship in a good supply of rum and red burgundy, and then spend my golden years making a complete picture out of the puzzle pieces in the old steamer trunk. That to me is the way any good romantic would look at his life: Live it first, then write it down before you go.

Any attempts at autobiography before the age of eighty seem pretty self-involved to me. There are a lot of smart middle-aged people but not many wise ones. That comes with "time on the water," as the fisherman says. So the following pages are another stab at completing a journal inspired by the trip that my wife planned for me to celebrate my fiftieth birthday, on December 25, 1996. I am glad to report that my first fifty years were, overall, a lot of goddamn fun. I just followed my instincts and kept my sense of humor. This journal narrates the trip itself as well as stories that the trip dredged up out of my past. I hope you enjoy the ride.

Questions and Answers

Now he lives in the islands
Fishes the pilin's
And drinks his Green Label each day
Writing his memoirs, losing his hearing
But he don't care what most people say
Cause through eighty-six years of perpetual motion
If he likes you, he'll smile and he'll say
Jimmy, some of it's magic, some of it's tragic
But I had a good life all the way
--"He Went to Paris"

Fifty. A mind-boggling thought for a war baby like me. Fifty is not "just another birthday." It is a reluctant milepost on the way to wherever it is we are meant to wind up. It can be approached in only two ways. First, it can be a ball of snakes that conjures up immediate thoughts of mortality and accountability. ("What have I done with my life?") Or, it can be a great excuse to reward yourself for just getting there. ("He who dies with the most toys wins.") I instinctively choose door number two.

I am not the kind of person to spend my fiftieth birthday in the self-help section of Borders bookstore looking for answers to questions that "have bothered me so," as somebody wrote once--those questions that somehow got taken off the multiple-choice quiz of life. It seems that here in America, in our presumably evolved "what about me" capitalistic culture, too many of us choose the wrong goals for the wrong reasons. Today spirituality and the search for deeper meaning are as confusing as the DNA evidence in the O. J. Simpson case. There is a labyrinth of choices, none of which seem to suit me. Granted, I have been too warped by Catholicism not to be cynical, but there are still too many men behind too many curtains for my taste. The creation, marketing, and selling of spirituality is as organized as a bingo game. By the time most of us war babies reached high school, we were pretty much derailed from the natural order of things. We were supposed to grow up, and that's where my problems started. Parents, teachers, coaches, and guidance counselors bombarded me with the same question: "What are you going to do with your life?" I didn't even want to think about that when I was fourteen. My teachers called me a daydreamer. They would write comments on my report card like, "He seems to live in a fantasy world and prefers that to paying serious attention to serious subject matters that will prepare him for life."

The life they were so hell-bent on preparing me for bored the living shit out of me. It seemed way too serious. I saw more meaning in the mysteries of the ocean and the planets than in theology or religion. I was too busy figuring out ways to skip school, go diving, and get laid. My heroes were not presidents; they were pirates. Emerging from adolescence with a healthy "lack of respect for the proper authorities,"x and a head full of romanticism and hero worship, I was able to come up with an answer.

Q. What are you going to do with your life?
A. Live a pretty interesting one.

I have been called a lot of things in these fifty years on the good old planet Earth, but the thing I believe I am the most is lucky. I have always looked at life as a voyage, mostly wonderful, sometimes frightening. In my family and friends I have discovered treasure more valuable than gold. I have seen and done things that I read about as a kid. I have dodged many storms and bounced across the bottom on occasion, but so far Lady Luck and the stars by which I steer have kept me off the rocks. I have paid attention when I had to and have made more right tacks than wrong ones to end up at this moment--with a thousand ports of call behind me and, I hope, a thousand more to see. My voyage was never a well-conceived plan, nor will it ever be. I have made it up as I went along.

The Fifty-Year Reality Check

A List of Things to Do by Fifty

Learn to play the guitar or the piano
Learn to cook
Play tennis
Learn another language
Surf
Read
Take flying lessons
Travel
Swim with dolphins
Start therapy
Go to New Orleans and Paris
Learn celestial navigation (or at least how to find the planets in your solar system)
Go to the library
Floss

Jimmy Buffett "has gregarious charm . . . and a bottomless well of stories to tell. . . . Reading A Pirate Looks at Fifty is like sitting with Buffett at a beachside bar, listening to him spin tales . . . discourse on life . . . and share nifty bits of geography and history."
--Time

"Fulfilling his peripatetic pirate lifestyle fantasies, rocker Jimmy Buffett took his family on a three-week trek around the Caribbean in celebration of his 50th. His colorful travelogue is interspersed with memoirs of his youth and music career--both of which revolve around his continuing search for the perfect fishing spot. But Buffett also imparts useful understandings gained from childhood through parenthood, and a valuable account of what it was like growing up in the '50s."
--USA Today

"The fun-loving Man from Margaritaville parses his hell-bent half-century."
--People

"Buffett takes the occasion of his fiftieth birthday to tell us about himself, and he does so with candor and modesty. The person who emerges is not the sort of rock star who trashes hotel rooms and slugs paparazzi, but a charming, decent, wry, kind, and contemplative man . . . . Buffett's evocation of the languid, louche Key West of the 1970's draws on the same well of affection as his best songs."
--The New York Times Book Review

"America's . . . good-time guy joins Hemingway, Dr. Seuss, and Steinbeck as one of the few who have topped both the fiction and nonfiction bestseller lists."
--Rolling Stone

Jimmy Buffett was a legend of popular culture as the composer of such classic songs as "Margaritaville," "Come Monday," and "Cheeseburger in Paradise." He recorded more than thirty albums, most of which went gold, platinum, or multiplatinum, and his sold-out concert tours were an annual rite of summer for his fans. In addition to his musical credits, Buffett is one of only seven authors with #1 New York Times bestsellers in both fiction (Where Is Joe Merchant?) and nonfiction (A Pirate Looks at Fifty). He had another New York Times bestseller with the short story collection Tales from Margaritaville. Jimmy Buffett died in 2023. In 2024, he was inducted into the Rock & Roll Hall of Fame in the Musical Excellence category.