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A Pirate Looks at Fifty
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A Pirate Looks at Fifty

3.81  ·  Rating Details ·  2,967 Ratings  ·  217 Reviews
For the millions of fans of Jimmy Buffett's music as well as his bestselling books, Tales From Margaritaville and Where Is Joe Merchant?, here is the ultimate Jimmy Buffett philosophy on life and how to live it.  As hard as it is to believe, the irrepressible Jimmy Buffett has hit the half-century mark and, in A PIRATE LOOKS AT 50, he brings us along on the remarkable jour ...more
Paperback, 420 pages
Published November 28th 1999 by Fawcett (first published June 2nd 1998)
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Jul 29, 2008 Travis rated it did not like it
Shelves: sucked-ass
Oddly enough, this was an incredibly interesting and profoundly boring book at the same time. The story unfolds as Jimmy Buffett, now turning 50, is preparing for a tour of the Caribbean. It reads almost as a travel guide, interspersed with flashbacks in the form of short stories of his more adventurous past. The short interesting chapters of adventure are constantly interrupted by pages upon pages of tedium. For example, the entire chapter devoted to his search for the perfect backpack to carry ...more
Sep 11, 2014 Dagny rated it really liked it  ·  review of another edition
This was a fun read. It took a while to get going on it, but then the pages just flew by. It recounts the Caribbean trip Jimmy took, along with family and friends, in celebration of his fiftieth birthday. Jimmy often tells the tale of his first trip to a particular spot and sometimes what prompted his wish to visit the area. When historical sites are visited, Jimmy provides an interesting bit of related history. There are great flying tales and fishing tales. I thought there could have been fewe ...more
M.A. Kropp
Jun 14, 2013 M.A. Kropp rated it really liked it
I’ve been a fan of Buffett’s music for a long time. Some of it is just pure fun, and others cut a bit closer to Life. I have tried to make Changes in Lattitudes, Changes in Attitudes an anthem for myself, and Trying to Reason With Huurricane Season is another I find inspiring. So I have wanted to read his autobiography for a long time.

The exoskeleton, if you will, of the book is the occasion of Buffett’s 50th birthday on Christmas Day, 1996. It is part autobiography, part travelogue, and all fas
Aaron Marvel
Jul 25, 2011 Aaron Marvel rated it really liked it
I read about 80% of this book about 5 years ago, and for reasons that are unclear to me, I put it down. So, fast forward to now, and I have finally finished this book. A truly enlightening read about one of my most favorite musicians of all time. No surprise, he lives a pretty exciting life, and one that makes me long for the time and fortune that only few and select successful careers seems to afford. For, having the time and the money is half the battle. A theme of life we all know too well, i ...more
May 28, 2010 Katie rated it it was amazing
Jimmy Buffett is my favorite musician of all-time, hands down. His music always makes me long to lay on the beach with a boat drink and his book gave me the same intense longing. It was certainly not a typical autobiography that starts at the beginning and moves chronologically through the author's life. Instead, Jimmy primarily recounts on the trip he took with his family to celebrate his 50th birthday. Interspersed into his detailed descriptions of flight plans and fishing trips are little fla ...more
Sep 11, 2012 Dan rated it did not like it
Shelves: memoir
Being a huge Jimmy Buffett fan I wanted to like this book, but I had to force myself to finish it. While there is a lot of good stuff here, the writing is too often very dry and didn't hold my attention. It isn't without its adventurous moments, but sadly they are too few and far between. I like Buffett as a storyteller, but his ability to turn a tale is almost totally lacking here. None of the characters he meets in his travels are treated with any flare or presented colorfully. As for his phil ...more
Sarah Sammis
Jul 21, 2012 Sarah Sammis rated it it was amazing
Shelves: pc, read-in-2006
I thoroughly enjoyed this memoir. Buffett wrote it during a family vacation to the Carribbean and South America over Christmas 1996 and New Years 1997. The trip inspired memories of his childhood and of other trips and he weaves these stories into the book. There are also wonderful asides about geography, history, movies, fiction and of course, music. Some of my favorite pieces of the memoir were the times he spent with his then 2 1/2 year old son Cameron. As a parent of a now 3 1/2 year son, I ...more
Sep 25, 2011 Louann rated it it was ok
This was just ok. The first 150 pages was tedious because it dwelled on minute details of private planes, boats and fly fishing. He rambles a lot and takes you two stories away from what he started to tell you. He will eventually come back around, but you have to hang on for all the subject changes. I enjoyed the part about his lean years and the parts about his wife, kids, close friends and the places he has vacationed. He has at least 2 more books that he has alluded to in this one. I am not s ...more
Tom Sakell
Jan 04, 2015 Tom Sakell rated it really liked it
I re-read this book every few years. Belongs in your bathroom and you can pick it up in any place.

Jimmy's been writing songs and books about friends, lovers, pirates and mother, mother ocean for so very long now. I liked it when he told tales about Jimmy -- a guy who thought he knew what he wanted to do and how to fit in. A divorce later and basically broke, he found he fit in quite well at the bottom and started singing about it. Interesting to read a guy who writes damn well write about how h
A globe trotting reminiscence by Jimmy Buffet. Not my normal read at all, but I do like some of his music & it was interesting. He gets side tracked a lot, which makes it better. We get a pretty good & honest over view of his life as he tells us about his 50th birthday & the trip he took to celebrate it. Within a few months of that age myself, I found it entertaining.
Bart Scott
Sep 20, 2013 Bart Scott rated it it was amazing
In many ways my Bible. In the past I've taken this book down and re-read it every year. It's a book you can just open to a random chapter and enjoy and keep right along with what's happening in the story. Jimmy is a master storyteller especially when telling tales from his real life, or as close to real life as you can get with Jimmy Buffett.
Jul 23, 2011 Kurt rated it did not like it
There are some nice moments here, where Jimmy talks about how hard it was to get started and about his misadventures in his early days. Other than that, though, it's a disgusting "I'm so great, I have money, everyone knows who I am" love letter to himself.
Mar 11, 2008 Carol rated it did not like it
Shelves: biographies
Never could stand Buffett and the whole Parrothead phenomenon. His good-old-boy schtick has always struck me as incredibly calculated. He's aw-shucks-ing it all the way to the bank. The book is just more self-aggrandizement.
C.R. Fladmark
Apr 10, 2015 C.R. Fladmark rated it really liked it
Jimmy is an amazing storyteller, in song and in writing. This is a story of the trip he took to celebrate his 50th birthday but is also interspersed with stories of his life,from childhood to college where he learns to play guitar; just to get girls,it turns out. A fun and interesting read.
Kason Motarsky
May 26, 2017 Kason Motarsky rated it it was amazing
A Pirate Looks at 50 is a comprehensive autobiography of the life of everybody's favorite drunk, Jimmy Buffett. Buffett takes an interesting approach to writing the book and bases it off of the trip he took around the caribbean while flashing back to pivotal points in his life and music career. The whole book is a collection of short stories loosely tied together but was executed perfectly. Throughout the entire book Buffett focuses on the theme of letting everything go and dealing with negative ...more
Ash Wilson
Jun 21, 2016 Ash Wilson rated it it was ok  ·  review of another edition
Shelves: music
I am a huge Jimmy Buffett fan. I’m a millennial Parrothead and not ashamed to say it! I LOVE his music, own all his records and concert dvds and consider him one of my all-time favorite musicians.

Because of that, I have been excitingly reading his books in order. The first two, “Tales from Margaritaville” tells of Jimmy’s ‘Semi-True Story’ adventures, and his well-known first complete work of fiction, “Where Is Joe Merchant” were both very fun and enjoyable reads that I loved nearly as much as
Nov 20, 2016 Judith rated it really liked it
One must be a Jimmy Buffett fan to enjoy this book. It was written 20 years ago. He will celebrate his 70th birthday this December 25th. I was motivated to read it as I had read Jimmy Buffett and Philosophy: the Porpoise Driven Life. There were many references to A Pirate Looks at Fifty in this book.
May 27, 2017 Carol rated it it was amazing
Loved going on vacation with the Buffet clan. Read while sailing in the Bahamas, fit right in.
Jan 26, 2017 Jeannie rated it it was amazing  ·  review of another edition
Awww my man Jimmy! I absolutely adore Jimmy Buffett so this book was a real treat for me. I wish I had the money to indulge my wanderlust like he can. sigh.
Jul 10, 2009 Adam rated it really liked it
Recommends it for: Pirates, Sailors, Islanders, Seaplane Pilots, Parrotheads, Rum Runners
Flying around the Caribbean, Central, and South America in a beautiful seaplane, sipping rum 'boat drinks,' fishing remote locations and generally being treated like a rockstar? Who wouldn't want to be Jimmy Buffett!

To be honest, and I feel bad saying this after finishing the book, I have never really been a 'fan' of this guitar wielding pirate, simply because, well, I haven't really been exposed to much to his music. As a kid, I remember my brother and I both loving to read Buffett's Caribbean
Dave Hanna
Sep 29, 2012 Dave Hanna rated it it was amazing
Like many people my age, I first became aware of Buffett thanks to the song "Margaritaville" and the album Changes in Latitude, Changes in Attitude. And while I have never denied enjoying his raucous party tunes, over the years I have come to appreciate and even prefer his quieter, more introspective songs. With lyrics such as "...painting liquid brushstrokes like Renoir" ("Beautiful Swimmers") and "...then sent me a smile as she reached for Flaubert" ("Love in the Library"), you know the man is ...more
Jan 07, 2008 Paul rated it liked it
I was given this book. Thus I did not know what to expect.

Reading the first couple of pages, I thought "oh, my - an autobiography. I hope it isn't boring".

I kept on reading. This book is really two autobiographies: One is about his three week trip around Central America, South America and the Caribbean. Intermixed in that story are bits about his youth and events surrounding him becoming "Jimmy Buffet, the Famous Singer guy".

I read the whole thing not for story #2 -- there are fascinating bits t
Oct 09, 2016 Geoff rated it really liked it
My Recommendation: If you have any interest in flying, fishing or traveling through the Caribbean or South America then this book would be an interesting read. You also might find it interesting as a case study of someone who grew up in the deep South who never left (for long at least) but found the alternative to the deep-rooted racism and insularity that seems to be making a come back.

My Response The first and only book I didn’t finish in time for this year’s autobiography book group. I did fi
Marie Zhuikov
Apr 28, 2015 Marie Zhuikov rated it it was ok
I decided to read this book after learning through a DNA site that I am distantly related to Mr. Buffet on my mother's side. About all I knew of him was his Margaritaville song, so I wanted to know more.

I enjoyed reading about his early life and his struggles to become who he is. But I found myself losing interest after that point -- after his struggles are over and he has all these first world problems of privilege that involve his own airplanes and fishing expeditions. I ended up skimming a lo
Sep 05, 2007 Tracey rated it liked it  ·  review of another edition
Finally finished Jimmy Buffett's A Pirate Looks at Fifty - I'm not sure why it took so long, as it's divvied up into nice bite-sized pieces ... probably influenced by his umpteen years as songwriter and performer

He chronicles a trip around the Caribbean, primarily flying his Grumman Albatross (photos - tho not of his) and occasionally meeting up with his wife and two younger children. He intersperses this travelogue with memoirs, sometimes tied in to where he is, other times not. He talks fondly
Kyle Hamilton
Mar 09, 2015 Kyle Hamilton rated it it was amazing
What an amazing book. I grew up on Jimmy Buffett music and as I got older instead of changing my music preferences, I became more into his music. I have listened to all of his albums and his music always gets me through rough patches in life. I really wanted to read this book because I had watched a few videos about Jimmy and heard about him through my dad but I wanted to get a full story on his life. The book is written in a way that takes you along on his birthday vacation while he keeps going ...more
Lou Pare-Lobinske
Jul 28, 2016 Lou Pare-Lobinske rated it liked it
Pros: 1. If you've listened to even a few Jimmy Buffett songs, you know he can tell a story. He's got more than one "no shit, there I was" yarns, including the backstory on "Jamaica Mistaica", that make the book entertaining.

2. He writes the book like a conversation, so when something reminds him of a past occurrence, he stops and talks about it.

3. He's well-read on the history of the locales he visits, which adds color.

4. I turn 50 in February. Because of his suggestion, I intend to stay up unt
Oct 31, 2009 Nancy rated it it was ok
I've been listening to Radio Margaritaville and saw this book at the library. There was way too much flying and fishing in the book for me. I skimmed much of it and skipped a lot.

One quote I liked:

"Bargaining should not be a part of life after fifty. By that time you know whether you can afford something or not."

Also the books Jimmy would take to a desert island:

The Adventures of Huckelberry Finn by Mark Twain
Treasure Island by Robert Louis Stevenson
Don't Stop the Carnival by Herman Wouk
Winds fr
Apr 25, 2016 Erin rated it really liked it
Before you take my review into account, I have to say that I am a HUGE Jimmy Buffett fan so this review is definitely biased, but still I have reasons I liked and dislikes parts. I really enjoy his writing style, it seems to click with how my own story telling might also flow. The beginning was a little tough to jump into, but once I was in I was reading rather obsessively. However, even though I love fishing, Jimmy's accounts of his fishing trips aren't the most exciting, but most the time I fi ...more
Nov 21, 2009 Travis rated it really liked it
Shelves: classics
For the amazing feat of not dying before he hit fifty, Jimmy Buffett decided he deserved a really good birthday present. So, he bought himself a seaplane and flew it and his family around the Carribean.

Part memoir and part boy's adventure tale, this book of Jimmy's travels reminds me why this guy is one of my heroes and makes me want to leave my comfy home ( especially now that winter is coming) and go see the world.

Jimmy is still a storyteller at heart, so while he brings people and places aliv
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James William "Jimmy" Buffett (born December 25, 1946) is a singer, songwriter, author, businessman, and recently a movie producer best known for his "island escapism" lifestyle and music including hits such as "Margaritaville" (No. 234 on RIAA's list of "Songs of the Century"), and "Come Monday". He has a devoted base of fans known as "Parrotheads". His band is called the Coral Reefer Band.

More about Jimmy Buffett...

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“One of the inescapable encumbrances of leading an interesting life is that there have to be moments when you almost lose it.” 89 likes
“later down the road of life, i made the discovery that salt water was also good for the mental abrasions one inevitably acquires on land.” 35 likes
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