I swear I didn’t mean for this to become a solid month of macabre and death-focused posts, but that’s the way this particular cookie crumbles. I have a wide array of partially completed posts in the queue at any given time; my drafts folder on Substack is an absolute mess. As a result, if something noteworthy happens, I might have something halfway done to add to.
In this case, I had a list of Jimmy Buffett songs compiled and sketched out. When the news came out that he had passed on September 1st (as a result of Merkel-cell carcinoma, a rare type of skin cancer), I knew I had to finish this article next. Since anyone with any real interest in his life has read at least one obituary, I’m not going to do a full write-up of his career like I normally would and I’ll condense it all into a shorter, sharper narrative.
Born on Christmas Day 1946 in Pascagoula, Mississippi (also the hometown of Channing Tatum, Trent Lott, and Uncle Elmer), James William Buffett was raised on the Gulf of Mexico for the majority of his childhood. After flunking out of Auburn, he attended the University of Southern Mississippi where he earned a degree in history. He also took advantage of the deferment system (and a failed physical) to avoid service in Vietnam. The most valuable thing he took from college was a pervasive love of music and some rudimentary skill with the guitar.
After college, he went to New Orleans, where he began busking and playing house parties. His second post graduation move (this time to Tennessee) led to a job with Billboard Magazine, where Buffett made connections within the music industry. Shortly thereafter, he signed a deal with Andy Williams’ tiny Barnaby Records label for two albums. They’re more explicitly folk-tinged than his later material, and sold quite poorly (with the first allegedly selling just 324 copies on initial release).
Following the second album’s release and a short-lived first marriage, Buffett escaped the Nashville scene to live in Key West. There he began working during the day as a professional sailor (following in his Newfoundland-born grandfather’s footsteps) while hanging out with the drug and alcohol fueled writers that had assembled at the bars in the area. It was here that the most well-known and most successful version of Jimmy Buffett came to life. After his pivot, he slowly but surely became a veritable rock and roll legend.
Buffett may not have invented what would become known as either “tropical rock” or “Gulf and Western” if you’re feeling frisky, but he became its biggest purveyor. By taking inspiration from such disparate corners as late Fifties doo-wop, early Sixties folk and “beach music”, late Sixties country gold, and early Seventies southern rock, the genre fused into everything your average Boomer frat brother wanted to hear. Each song was at its heart a simple hummable tune that could be easily played on a stray acoustic found at the remnants of a clambake by a still-inebriated general studies major. In concert, the music incorporated pedal steel guitars, a virtual choir of backing singers, and an ever-present horn section to tie it all together.
The real magic for his career came when those same fraternity brothers started to enter the workforce, earning far more than their predecessors with all kinds of disposable income to blow. What would they spend that money on? Turns out it was a lot of Jimmy Buffett concerts, Jimmy Buffett memorabilia, and every sort of branded experience under the sun. His songs are pretty good, but the man was an absolute master when it came to marketing oneself. Buffett was able to expand into many different markets, including restaurants, resorts, cruises, beers, casinos, and his own line of hemp-based products. There are even three retirement communities in Florida and South Carolina with “Margaritaville” branding.
Buffett’s concerts, especially once the Grateful Dead stopped touring, became the focal point for Boomer music aficionados. Tickets were pricy, tailgating was epic, and crowd rowdiness was legendary. Timothy B. Schmit (then playing with Buffett’s band in between stints with the Eagles) compared the concertgoers to the Deadheads, remarking that with their Hawaiian print shirts they were closer to Parrot Heads. With that stray thought, an entire industry blossomed.
To be blunt, all you really need to know about Jimmy Buffett’s music can be summed up in one convenient package: 1985’s greatest hits compilation Songs You Know By Heart. With these thirteen songs (including all of the “Big 8” that were played at every concert), you get a fairly complete picture of the Jimmy Buffett experience. Me being my idiosyncratic self, I didn’t just copy and paste the track listing into the Substack editor to make my own list. Looking back, that would have made things easier. Instead, I put together my own interpretation of what I believe to be the best Buffett songs. There is a lot of overlap, though. Let’s start with number ten…
10. Come Monday
After the dissolution of his first marriage, Jimmy met his second wife Jane while holed up in Key West. “Come Monday” from Living and Dying in 3/4 Time was written about her, and it went on to become his first Top 40 single. Sitting squarely on the “easy listening” side of country, this song is a remnant of when Dunhill (his second record label) tried to make him into the next Jim Croce following his untimely passing.
9. Volcano
Buffett’s worries about a volcano eruption seem moderately fantastical, but he had his reasons. Recorded in Montserrat at AIR Studios in 1979, the titular “Volcano” was referring to Soufrière Hills on the island that had some seismic activity just a decade previous. In 1995 (following the destruction or large portions of Montserrat in 1989 thanks to Hurricane Hugo), the volcano actually erupted and hasn’t really stopped. As a result, more than half the island is now uninhabitable. Man, I keep trying to be light-hearted in these articles but it’s just not happening.
8. Grapefruit - Juicy Fruit
A White Sport Coat and a Pink Crustacean is the first “real” Jimmy Buffett album, once he embraced his Gulf roots. “Grapefruit” is a rather delicately constructed song, more of an imagist tone poem than anything, about a fairly indelicate topic. Buffett was working as a fishing guide at night while playing in a bar called Howie’s Lounge during the days. While there he would meet all sorts of young ladies looking for a distraction at the shore, which he was more than willing to provide. Besides the novelty song “Why Don’t We Get Drunk”, this song is the most notable from that first album.
7. Fins
“Fins” might be the least “countryfied” song in this list, having more in common with The Knack or Eddie Money than anything with a twang. It’s only the harmonica solo from longtime Coral Reefer Band member Greg “Fingers” Taylor that really separates it from the pack. The song’s lyrics are responsible for one of the trademark Parrothead concert fixtures, the “Land Shark” collective dance. Take a look at this version from the Gulf Shores Relief Concert in 2010:
6. Son of a Son of Sailor
Despite the popular conception of his music, very few of Jimmy Buffett’s songs are actually about sailing; most are just paeans to the beachfront bars and their patrons. This is one of those exceptions, though, as it focuses on the freedom and adventure that comes with the open sea. I’m a landlubber myself, and have no real interest in traveling on the ocean itself. I’m more content to read dozens of books about heroes and crooks. It’s a definite slowdown in terms of the album version; live renditions often pick up the pace considerably.
5. A Pirate Looks at Forty
The titular pirate is not Jimmy himself, but instead is Philip Clark, a failed drug smuggler he met in the first few weeks after moving to Key West. The song is biographical, capturing how Clark was reflective about his relative lack of success during his long conversations with Buffett at the Chart Room where he played shows. Buffett himself was accused of smuggling drugs in 2006 in Saint Tropez; customs officials mistook his prescription B-vitamin supplements for MDMA when they searched his private jet. He paid a small fine in order to expedite the legal process, or put more simply bribed his way out of a jam.
4. Changes in Latitudes, Changes in Attitudes
Take a look at the video above to get a good encapsulation of what it meant to be a Parrothead in the 2010’s. There are lots of mermaids, socks with sandals, bright Hawaiian print shirts, and even an Elvis impersonator or two. The audience is overwhelmingly middle-aged, white, and affluent. The disposable income is practically palpable. The song itself celebrates the escapist philosophy necessary to deal with the stresses of modern life for the upper middle class: vacations to exotic locales, sprinkled with copious amounts of alcohol.
3. Pencil Thin Mustache
Speaking of Boomer-centric nostalgia, “Pencil Thin Mustache” is a veritable cornucopia of references and allusions that only hit correctly if you’re in the Boomer demographic. Musically, it’s half jazz manouche and half western swing: equal parts Django Reinhardt and Bob Wills, played at a leisurely tempo that solidly sits in the pocket. Much like the lyrics are rooted in the Forties, so is the music. It’s atypical of Buffett’s work, in the best way.
2. Margaritaville
You knew it had to be on here, right? I’d feel foolish leaving it out. But alas it’s not the number one entry. “Margaritaville” is a song big enough to build an entire brand around, and Buffett did. It was a highlight of every concert after its release on the Changes in Latitudes, Changes in Attitudes album in 1977, spurring a singalong each time. Of all of Buffett’s discography, this is also the one with the most substantial radio exposure. Despite its pervasiveness it only reached number eight on its initial release, relying on long-tail play to create its lasting impression on audiences. As a bonus for concert goers, there’s even a secret verse. Do you know it?
Old men in tank tops,
Cruisin' the gift shops,
Checkin' out chiquitas, down by the shore
They dream about weight loss,
Wish they could be their own boss
Those three-day vacations can be such a bore
1. Cheeseburger in Paradise
As a man who loves food (perhaps too much, according to my doctor), I had to select this ode to the delectable cheeseburger as my number one. It might not be the “best”, but it’s the one I want to sing along to the most. It’s uplifting, it’s optimistic, it’s even hopeful. There’s no trace of the frequently featured melancholy that laces many of Jimmy Buffett’s work; this is no opportunity for self-reflection, but instead a simple praise song about cheeseburgers. Is it a novelty song? Does it matter? If I’m going to listen to Buffett, I’ll start here.
Thank you for joining me this week, and thank you to those of you that reached out after last week’s piece. I appreciate each one of you. Next week, I’ll most likely have another short article while I percolate on something longer for later. See you next time, space cowboys.