Jimmy Buffett - A Pirate Looks at Fifty

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Jimmy Buffett Hits the Big Five- Oh!

Apr 27, 2005 (Updated Apr 30, 2005)
Review by  
Rated a Very Helpful Review

Pros:The personal stories; The creative writing

Cons:The parts about his birthday travel are a little repetitious.

The Bottom Line: This is a fun book for its storytelling nature and its creativity. It also serves to provide some insight into Buffett's life story.

Greetings, fellow Epinions members! This review is part three in a five- part solo write- off series titled “Rock and Roll All Nite”. These books I’m about to review celebrate some of the biggest names in rock and pop music, providing insight into their music and their personal lives. Enjoy!

Reaching milestone birthdays is a bittersweet feeling for most people. We look forward to turning 13, 16, 18, and 21, because these ages usually bring with them greater freedom and greater independence and responsibility. But beyond the age of 21, the “accomplishment” of watching the digits climb higher on our biological calendar isn’t much fun anymore. Once the ages of adulthood have been achieved, there isn’t much anticipation or excitement in getting older.

Whether we like it or not, however, family and friends are going to be prepared for celebrations each time another decade is reached. And one man who knows quite a bit about celebrations of all types is also the author of a book he wrote when he was ready to reach the ripe old age of 50. The man is musician and entertainer Jimmy Buffett and in this book, A Pirate Looks at Fifty, Buffett shares both his birthday adventures and some of his feelings on life when he hit the milestone half- century mark in 1996.

Basic Contents of This Book:

This 420- page book is divided into the following eleven sections:

Introduction: Trouble on the Horizon
1. Time on the Water
2. Time in the Air
3. Time on the Bottom
4. Leaving Florida
5. Cuba and the Cayman Islands: Latitudes and Attitudes
6. Costa Rica: Pura Vida
7. The Songline: Mother, Mother Ocean
8. Another New Year
9. Colombia: Send Lawyers, Guns, and Money
10. The Amazon: A Second Look
11. The Islands: The Spicy Kind of Life


Jimmy Buffett was born on Christmas day, 1946, in Pascagoula, Mississippi. His family later took up residence in Mobile, Alabama, where Buffett grew up and attended private school. It was here in Mobile that Buffett developed his love of the sea and warm weather. And because of his love of warm, tropical waters, it made sense that he celebrate his fiftieth birthday in the area he loves more than any other: The islands and nations surrounding the Caribbean Sea. In the first six sections, Buffett talks about his vacation trip in the Caribbean region. He sets off on an airplane named the “Hemisphere Dancer” leaving Florida behind for the warmer latitudes, making stops in the Cayman Islands and Costa Rica before heading to Columbia and the Amazon River in South America. He and his family then island- hop back to the U.S., with stops in Trinidad & Tobago; Grenada; the Grenadines; Martinique; and other places on the trip back home.

While Buffett traverses the Caribbean and the northern part of the South American continent, he often stops talking about traveling and harkens back to other experiences he has had in these same areas. He also talks about history and geography, and there are a few maps in the book that show the approximate path of his flight. When he isn’t talking about history or geography, he is giving a glimpse into his personal life, with talk about life in Mobile; the college experience; and his career as a singer.

Every so often, Buffett includes a summary of his whereabouts at a particular place, complete with the latitude and longitude of his position, the altitude, wind speed, etc. He also talks about the people he meets as he hops around from island to island and from place to place, seeking new food, good drinks, and opportunities for good fishing.

Buffett’s three- week vacation/birthday celebration ends in early January, 1997, back in the state of Florida. Twenty- one days of reflection and adventure are now behind him as he prepares for (hopefully) another few decades of musical entertainment and of personal fun in his beloved Caribbean.

Final Thoughts:

Jimmy Buffett is a singer/songwriter who has been entertaining audiences for more than thirty years. His loyal followers, affectionately known as “Parrotheads”, have helped make Buffett one of the most successful touring musical artists in history. Buffett’s chart success has been limited, but his shows are almost always sellouts. He believes in working hard and playing hard, so it was only natural that he would have an elaborate celebration planned when he hit the big five- o.

This book is part travel log, part autobiography. First and foremost, Buffett intended this as a travel diary about his fiftieth birthday celebration. He kept notes about all the places he visited, his global positioning, the weather, the people, and other facts, assembling them together in this book. His writing follows in chronological order when he is describing the events of his three- week jaunt in the Caribbean and in South America. But when he talks about personal topics and his past, he lets his mind flow freely from one era to the next, discussing important events in his life and how they have affected his growth and beliefs as an adult and as a successful musical artist.

The majority of this book talks about the places, the people, the activities, and the fun created by taking a long trip like this in one’s own airplane. Besides being an avid sailor, Buffett is also a pilot, and he decided that his birthday would be more memorable and more of an adventure if he flew the airplane himself from place to place. This adds an element of suspense to this book, because with Buffett inside the cockpit, you (and he) never really know what will happen. I learned from reading this book that Buffett had been in a plane accident once before, and I’m sure this event is still in his memory. You can tell by the way he describes his flight that airplane malfunction is very much on his mind at every moment.

When Buffett is talking about his own past, he is opinionated and open. These personal excerpts comprise a smaller part of the book and they are interwoven in various places. Wherever Buffett can find a place to sidetrack himself for a few minutes, he takes advantage of the situation and tells you a story about his past. These parts of the book are my personal favorites, because they let you know the man behind the music. Buffett shares his own history with the reader, with talk about his early life in Mobile, his interest in music, his women, his experience with drugs, his time attending college, and his present- life as a family man and touring pop phenomenon. He reflects on his life thus far with great satisfaction and few regrets. Many might be surprised to discover that Buffett’s interest in music was spurred not because of a great love of singing, but because he quickly discovered that guys who played music usually scored easily with the chicks. It was in college that he first developed his interest in music when he noticed women flocking around anyone who could play an instrument. He decided to take up guitar himself, a college buddy taught him how to play, and the rest is history.

One other thing I discovered about Jimmy Buffett from reading this book is that the guy has some great creative talent as a writer. Let’s face it- writing a book that deals mainly with a three week vacation trip and the maneuvering of an airplane sounds rather mundane and uninteresting. But Buffett’s creative skill as a writer makes it enjoyable regardless. He shows that his talent for writing a song can easily be applied to the writing of a book of non- fiction. He has a very vivid and colorful way of describing ordinary things and actions that keeps his reading interesting even when the topic itself is rather dull.

When I first took up the task of reading this book, I was a little disappointed at first. The first few sections seemed too concerned with his vacation trip for his fiftieth birthday, and it started to get a little bit repetitious after a while. I knew going in that this was a book about his birthday and the celebration that followed, but I wanted to know more about the man from Margaritaville; his life, his interests outside of music; his family; his rise to the top; and other personal topics. As I read more, Buffett slowly began talking about things that got him where he is today, providing some good insight into his past. The more I read, the more I liked the book. And, as I have stated before, I couldn’t help but notice Buffett’s penchant for creative writing. Even though I wanted to know more about him as a person and I wasn’t that excited listening to him ramble on and on about how it felt to be flying over Central America at 20,000 feet, I was still able to hold my interest thanks to the creativity of Buffett’s words. I haven’t read any of Buffett’s fiction books, but I would bet they are probably pretty good, given his mastery of creative communication.

Overall, “A Pirate Looks at Fifty” is a very good book for all Parrotheads and others to sit back with and enjoy. It’s like joining Jimmy Buffett on a sandy stretch of land by the ocean, sitting back in a cozy beach chair with a rum drink in hand, and listening to Buffett tell his tales of adventure, both past and present. It’s a personal and entertaining read from the gregarious, friendly, charming, and always affable man from Margaritaville, Mr. Jimmy Buffett.

Be sure to read the other reviews in this write- off series:

The Long, Hard Road out of Hell, by Marilyn Manson

Kiss and Make Up, by Gene Simmons

Catch a Fire, about Bob Marley

No One Here Gets Out Alive, about Jim Morrison

Recommend this product? Yes

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