A1A's album art


Coconut bras, plush parrot hats, and Hawaiian leis decorate an audience of 35,000 singing along to a 69 year old sporting aviators and sandals—“why don’t we get drunk and screw?”. Beyond the concert entrance is a sea of decorated party buses and cars, where stragglers sing along as they happily bar-hop in the tailgate from one DIY margarita bar to the next. From this scene, it can be hard to believe that this 69 year old pirate began as a “shy ex-altar boy from Alabama”. Like many, Jimmy Buffett’s roller coaster of a journey began with the toe dip into adulthood—college.

Parents, teachers, coaches, and guidance counselors bombarded me with the same question: “What are you going to do with your life?” I didn’t want to think about that when I was fourteen. My teachers called me a daydreamer. They would write comments on the 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.” […] I saw more meaning in the mysteries of the ocean and the planets than in theology or religion. […] My heroes were not presidents; they were pirates. Emerging from adolescence with a healthy “lack of respect for authorities,” 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.

Jimmy Buffett “A Pirate Looks at Fifty”

Hundreds of miles north of the Mobile shoreline in a fraternity pledge swap party at Auburn University, a young, shy Buffett floundered in the social scene like a fish out of water. Defeated and on the verge of leaving the party, the sound of a guitar and a plethora of spectating college girls caught his attention. Mesmerized by the freshman player’s ability to work a crowd and play requested songs seemingly from memory, Buffett switched his direction from the door to the source of the music, joined in the crowd, and sang along. After the party, while many probably had the songs of the night still playing in their head, Buffett was left with the nagging question: how did a short, out-of-shape freshman with acne scars work a party, play requested songs on the spot, and attract the attention of so many people like that? To Buffett, what the freshman could do was magic. The secret to that magic? Three chords.

That night under the instruction of the freshman, Buffett, within a pint of Scotch time, learned the D chord, and by the end of the night, he was hooked. It was not long until he learned the rest of the chords and, overcoming his shyness, joined alongside the freshman during pledge swaps, playing duets and having a blast. With his focus revolving around learning the guitar and playing at his fraternities parties, it comes to no surprise that Buffett flunked out of Auburn by his spring semester. However, Buffett did not leave Auburn empty handed. He had learned something far more valuable than any classroom could teach him—those three chords and a taste of the thrill of playing for others.

However, not all was sunshine and rainbows for Buffett. This was the 60s, and people like Buffett were prime draft targets to be sent overseas. Knowing that he would have to face his father and a likely impending rice field grave overseas, Buffett traded the direct highway route for the scenic back country roads back home to Mobile, passing through Pearl River Junior College in Poplarville on the way. Perhaps he was looking for any way to postpone his homecoming or perhaps the thought of playing guitar for the college girls crossing the street urged him to stop, but for reasons even he is not sure of, Buffett pulled off the highway and paid a visit to the Administrative building. Even with his terrible GPA, he left Poplarville enrolled as a freshman on probation at Pearl River Junior College. Thus marking one of Buffett’s many life events that add credence to him either having a horseshoe up his ass or someone looking out for him upstairs—in most cases, it is probably both. With a quick visit back home to leave a note and pack, Buffett changed his fate from camo, boots, and a rifle to rag tops, books, and his guitar.

However, Buffett’s enrollment bought him more than avoidance of the draft. More importantly, it bought him access to the growing hub of folk music on the weekends, New Orleans and Biloxi. Buffett’s true lectures took place on Saturday nights in The Bayou Room and he did his homework on street corners—observing other performers and street performing until morning.

After forming his own folk group, transferring to the University of Southern Mississippi, and evolving from observer to performer at The Bayou Room, Buffett spent an increasing amount of time in New Orleans, “[making] up for the lost time [he] had spent as an altar boy”. Furthermore, his performing experience drastically increased as his weeks consisted of four days performing in the French Quarter with the remaining three days spent doing night classes. Needless to say, time quickly slipped through his fingers like sand, and he soon found himself face to face with the dreadful reality of having a diploma in one hand and a 1A notice1 in the other. Luckily, Buffett had another golden horseshoe up his ass, except this time it was in the shape of a stomach ulcer. With a nice NPQ stamp and a switch to the 1Y draft classification, Buffett was again clear of Vietnam. After marriage, a bar gig, employment at Billboard magazine, and a music publisher contract, Buffett headed to his new landlocked life in Nashville.

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 most is lucky.

Jimmy Buffett “A Pirate Looks at Fifty”

After a record deal with Barnaby Records—Buffett, dreaming of his future as a star—enthusiastically launched his first record Down to Earth and left his position at Billboard. However, as fast as this good news came, the prospect of Buffett having a big break vanished. His first record failed to sell after a promotion trip to Dallas, Texas, leaving Buffett in debt with no more promotion band. To try to bail out his sinking ship of a new career and pay off his debt, he struggled to get back momentum performing solo again. However, to add extra holes to the ship, Buffett’s increased activism in anti-Vietnam protests and his vocal record business grumblings with other struggling performers did not sit well for his industry relations nor his marriage. In the end, his new shiny boat of a career hit rock bottom. All Buffett was left with was debt, a failed marriage, and of course, his luck.

Queue a deus ex machina in the form of country singer and songwriter, Jerry Jeff Walker. Walker and Buffett connected during Buffett’s Billboard days, and around the time of Buffett’s record flop, Walker paid a visit while in town. Like any friendly visit, the two shared drinks and long talks in which Walker extended an invitation for Buffett to visit him in his new home in Coconut Grove, Miami. After Walker’s visit, the sound and name of Coconut Grove stayed with Buffett, evoking warm thoughts to Buffett’s mind. He was reminded of how much he missed his mother: mother ocean and the warm sea salt mist of her waves. He had an escape with Walker, and with some networking with the previous club owners he worked with, he landed a job at the Flick—a Miami club notorious for its booking difficulty due to its prime location. With an expired TWA credit card left over from his Billboard and marriage days and Buffett’s sly charming at the ticket counter, the pirate bought a ticket and headed to Miami to board Walker’s 1947 Packard—The Flying Lady.

When I had left Nashville that morning, it was thirty-one degrees and raining. I was broke and getting a divorce. My career was in cold storage, and I had a cracked front tooth. Four hours later, I was sitting under a cluster of royal palms with a breeze coming off Biscayne Bay. I was barefoot, in shorts and a T-shirt, eating lobster salad and drinking ice-cold beer, laughing and listening to Murphy’s stories of Key West.

Jimmy Buffett “A Pirate Looks at Fifty”

Over Buffett’s two years in Nashville, every day his dry gills called his thoughts back to the ocean. He saw Nashville as a means to an end. From his time as a “normal businessman” at Billboard to his brief taste of the touring band lifestyle underneath Barnaby Records, Buffett’s sights never deviated from the true goal—life on an island. The warm sun of Miami—evaporating worries away—gave Buffett a clear perspective on his failure in Nashville; his heart, soul, and mind belonged to the culture, climate, and geography of the tropics and the ocean, not to that of the Blue Ridge State. To continue living and working in Nashville would mean the continuation of trying to be someone he was not.

The following Monday, after settling in at Walker’s and getting a tour of Coconut Grove’s popular sites, Buffett headed to the Flick to prepare for his opening night. However, Buffett’s guitar remained silent that night. Upon his arrival to the not-so-elegant strip mall sandwiched club, the club owner, who was more engaged scrupulously checking his recently bought fruit, dismissively notified Buffett that he would not start until two weeks from then. Even though the onus laid on the club owner for making the booking error, a verklempt Buffett dared not challenge the man who held the keys to his one gig in Miami as well as the network of other club owners. Two weeks it was.

When Buffett returned and relayed the news of the work delay, Walker’s girlfriend offered a simple suggestion, a suggestion which culminated in the pinnacle moment that would ultimately position Buffett to fulfill his dream of life on an island.

“Hell, Jerry Jeff, let’s go to Key West.”

However, Key West would end up serving Buffett as more than just a dream home. Like French Quarter, Buffett’s Caribbean soul resonated with the dive bars and culture of the Key West. However, unlike New Orleans, living in the Key West provided him with more than just performing experience. The Key West served as a rich source and provider of inspiration and many stories that, in turn, fostered the beginning of his wildly successful music career.

After some mechanical repairs, Walker, his girlfriend, and Buffett boarded the Flying Lady towards U.S. 1. Destination: A1A, Key West.

The Storyteller

When Buffett made it to Coconut Grove and reconnected his soul with the tropics, he found happiness and purpose in life—the momentous “Migration” for Buffett. With his reconnection and happiness with the tropics also came confusion. In “Migration”, Buffett expresses his confusion and frustration at some people’s blindness to the beauty around them, whether it be old retirees who never venture beyond to the beauty outside of their condos in Florida or the “bastards” who are too blind to see their pollution of the Florida Keys with commercial America and mobile homes. However, Buffett’s confusion and frustration at others quickly transitions. Buffett comes across the revelation that his life, without the draft, failing marriage, and floundering career in Nashville, was finally looking hopeful and completely his to direct. Sure he made a lot of mistakes, but it is now time for him learn his lessons, refocus his life, and have some fun. After all, in a fast, excited spew of liberation in a form of a rebuttal to those who are blind to the beauty, he announces that he is sure as hell not going to end up like the an old condo retiree.

Well now, If I ever live to be an old man,
I’m going to sail down to Martinique.
I’m going to buy me a sweat stained Bogart suit
And an African Parakeet.
And then I will sit him on my shoulder
And open my trusty old mind.
I’m going to teach him how to fuss,
Teach him how to cuss,
And pull the cork out of a bottle of wine.

“Migration” A1A

A few years after Buffett’s first arrival in Key West, Buffett, with help of ‘Fingers’ Taylor, formed The Coral Reefer Band, and, in the same year A1A dropped, Buffett and the band tackled serious touring and roadwork until 1982. The saying is that absence makes the heart grow fonder, and, as shown in Buffett’s romantic love song for the island, “Tin Cup Chalice”, the upcoming serious roadwork for Buffett sure did make his heart grow fonder for Key West. The long ringing high pitched chords and the long-drawn, melancholy harmonica throughout “Tin Cup Chalice” provide a tasteful hint of tropical atmosphere as well as perfectly convey Buffett’s homesick caused longing. While the Key West was integral to Buffett’s inspiration and success, the subsequent success the island helped facilitate would also be the reason that Buffett would leave the island for touring and roadwork. While Buffett is certainly not resentful at this, in “Tin Cup Chalice”, it is clear that his heart and soul are tied to and long to be back in the sea salt air and bright sun of the island.

I want to be there,
I want to go back down and die beside the sea there.
With a tin cup for a chalice fill it up with good red wine,
And I’m-a chewin’ on a honeysuckle vine.

“Tin Cup Chalice” A1A

The Stories

In Key West, Buffett has met some interesting characters each with their own stories to tell. Many of these characters have made their way to serve as inspiration for songs—most notably Buffett’s real pirate friend, Phillip Clark, of the Key West who “A Pirate Looks at Forty” was written for.

This is a song… I guess I wrote this for an old friend of mine a few years back who could just not find his occupation in the 20th century. So, he just chose to live in a fantasy world and I looked at him and I went well what the hell’s wrong with that?

Jimmy Buffett Feeding Frenzy [Live]

While this song is written as a eulogy for Clark, I can not help but hear some autobiographical inspiration from the ‘helpless romantic’ himself. However, autobiographical influence or not, Buffett, with his fascination with and respect for mother ocean and his romantic, heroic interpretation of pirates and the pirate lifestyle, wrote an empathetic tribute to Clark that I am sure would make the pirate smile.

In addition to possibly meeting Phillip Clark at one of the bars at Key West in the 70s, if one were to venture to City Hall on a Friday night they would hear music coming from underneath a big parachute, and they would possibly find Buffett taking a quick pass to spectate between tours of Duval Street. On those Friday nights, a square dance group called the “Nautical Wheelers” would gather underneath the parachute and dance the night away2. The observant eye would also possibly catch a drunk Clark tied to a channel marker out at sea.

For an artist with an impressive 29 albums, excluding live recordings and compilation albums, why A1A? After all, when taking into account cover songs, the album barely reaches LP length. To put it simply, I believe that the remaining songs in A1A encapsulate a special time in Buffett’s life. Through songs like “Nautical Wheelers” and “A Pirate Looks at Forty”, the album provides the listener with a looking glass into the culture and people of early 70s Key West and, subsequently, the album also gives a fresh glimpse into Buffett’s bout of inspiration and creativity from his first years on the island. Furthermore, the sad, sour, retrospective career failure musings in “Dallas”, the drunken ‘fly by the seat of your pants’ wanderings and lifestyle described in “Presents to Send You”, and the pit-stop styled autobiographical up’s and down’s recounted in “Life Is Just A Tire Swing” present an interesting time-locked perspective on Buffett’s feelings, life, and worldview at this pivotal time in his life and career. Indeed, this album not only gives a glimpse into the tropical foundation of Buffett’s career, but with the album also containing Buffett staples such as “Pirate Looks at Forty”, “Trying to Reason with Hurricane Season”, “Nautical Wheelers”, and “Tin Cup Chalice”, I would argue that A1A is the tropical foundation of Buffett’s career. So, I would encourage you to not dismiss Jimmy Buffett as a goofy, cult artist whose song lines only consist of the subject matters of margaritas and cheeseburgers. Through the crowd of parrotheads up on the stage, there is a pirate, sailor, and pilot behind those aviators who definitely has stories to tell.


  1. The selective service breaks men up into classifications during draft time. 1A indicates the candidate is ready for military service. ↩︎

  2. There is a great video of a young Buffett performing “Nautical Wheelers” to a crowd in Key West. I love this video as it is so much fun to see a more intimate performance with Buffett. It is also a blast to watch all the different audience members really get into the performance. ↩︎