Jimmy Buffett “Fruitcakes”
For the last twenty years “product market fit” has served as the shorthand buzzphrase to denote startup viability. The term, popularized by venture capitalist Marc Andreesen, describes the conditions wherein a business has obtained evidence of sufficient, sustainable and — perhaps most of all — scalable demand for their product. Techy types might use “product market fit” around the achievement of some key sales metric. Brand marketers might use it when oversized product demand is detected. But I often use the phrase to describe musicians that demonstrate unusual insight and responsiveness to their audience. Think Bruce in the 80s or Phish in the 90s or Taylor today or AC/DC for the last fifty years — artists who fully understand what their audience wants, why they want it and how to give it to them.
To be clear, many great artists find massive success without the same level of audience-centricity as Bruce, Phish and Taylor. Some thrive while misunderstanding — or even resenting — their fans. But it’s these instances of deep and mutual connection that are the rarest and most compelling for me, both as a fan and an entrepreneur. To my mind, the first two factors in product market fit are the easier ones to solve for. First, “sufficiency” — is the market big enough? And next, “sustainability” — will the demand survive or not? Over the years, many artists have obsessively cultivated and nurtured audiences large and devoted enough to build careers upon. But it’s that third factor — scalability — which separates the merely successful names from the transcendent superstars.
For instance, The Ramones had two out of three. Same with Motorhead. Black Sabbath. Slayer. The Smiths. Insane Clown Posse. These are acts who — like Bruce, Phish and Taylor — optimized their product delivery system around the desires of their market. Their music and their performances are direct fulfillment of their fans’ specific hopes and dreams. And yet, as wildly, titanically successful as they are, I do not think any of these greats understood product market fit as thoroughly as James William Buffett — the Mayor of Margaritaville, the King of the Keys, the Prince of the Parrotheads. Jimmy Buffett was the very successful musician turned unthinkably successful entrepreneur whose music, like his brand, was rooted in an idea as ancient as it is true: escape sells.
There are many facets to Buffett’s appeal. His twang was Country friendly. His Jangle was not so far from the Laurel Canyon sound. His compositions were simple and radically. He looked like the kind of guy you might find at a ballgame or a Grateful Dead show or on the golf course or — it almost goes without saying — at a bar while on vacation. In almost every conceivable manner, and more so than any artist before or since, Jimmy Buffett collapsed the space between his “signifier” — fun loving, middle-aged, singer-songrwiter, beach bum on permanent vacation — with his “signified” — semi-tropical, middle-aged, musical escapism.
This is not to denigrate Buffett’s skill as a maker of music. He managed to combine a writerly flair for characters and place with an abiding sense of melody. Yes — he wrote a bunch of cloying songs and many more kind of boring songs. But the guy does not have very many “bad songs,” if that phrase is to describe something formally shoddy. Your mileage will vary on his hallmarks — Caribbean jerked, Polynesian blended New Folk (Prine), Outlaw Country (Kristofferson) and West Coast Singer Songwriter (Browne). However, it’s hard to debate the novelty of his innovation. Buffett was not exactly the first or the best, but he was absolutely an original.
The magic trick that he pulled off — the thing that also maddened critics — was his capacity to be weird and tedious at the same time. Buffett was both impossibly consistent and almost never insistent. He was both goofy and middle of the road. His songs — about old surfers, washed up rogues, lovable weirdos and, most of all, sunset getaways — emitted a specific vibe but were oddly devoid of feeling. Some of this was a matter of content and theme: escapism. But a lot of it had to do with the volume and tenor of his songs. The lack of lead guitars. An accurate but limited vocal range. Congas and steel drums instead of bass and cymbals. The cumulative effect of his sorcery is that you can easily sing along, sway along and smile along to his music and words, but you can just as easily ignore them, nap to them or or feel nothing at all. He operates in a realm between gentle pleasure and comatose. But we’ve come to learn that his realm — a once mythical, now mall-based place he calls “Margaritaville” — is also a destination that Americans crave. Overworked, overtired, overstimulated, overextended listeners like their Rock and Roll and their Country music and their Folk music and even, occasionally, their Reggae. But they love the experience of having all of those things while also being four piña coladas in at a beachside Tiki Bar.
By the mid-Eighties, Buffett’s product market fit had proven to be both sufficient and sustainable. But the scalability was still up for debate. He’d had a run of Gold and Platinum records, but no Multi-Platinum affairs. He’d had a few Top Forty hits and one that hula-ed its way into the Top Ten, but he’d never topped the charts. He existed somewhere between extremely successful cult act and two hit wonder. He’d penned a few timeless novelty songs, a handful of exceedingly great Country Rockers, including “Livingston Saturday Night” and “The Great Filling Station Holdup,” and some lovely ballads, like “Come Monday” and “Son of a Son of a Sailor.” He could show up and be greeted by parking lots full of coconut bikini, grass skirt clad fans. But, up to that point, Jimmy Buffett had not fulfilled his destiny. Or, more specifically, he’d not effectively scaled his product market fit.
That leap started in the later Eighties, first with his pivot from Gulf Shores souvenir shop owner to Key West restaurateur and merch magnate. Then came the books — ”Tales from Margaritaville,” from 1989, and “Where Is Joe Merchant?,” from 1992, both spent ages on the New York Times Best Seller list. In 1992, Buffett also formed his own indie record label, Margaritaville Records. And this was all, of course, just the beginning. The Margaritaville-ization of America continues to this day. Buffett’s restaurant on the Las Vegas strip was at one time the most lucrative eatery in the country. There was Margaritaville beer, foods, furniture, casinos and, inevitably, retirement communities. When Buffett died in 2023, he was not simply a close friend to Warren Buffett — the legendary investor. He was also, like Warren, a billionaire.
Some musicians — like Paul McCartney — accumulate gargantuan fortune’s almost entirely on the basis of musical talent. Others — like Mick Jagger, Bruce Springsteen and Taylor Swift — get there through a combination of talent, tirelessness and market savvy. Buffett is something of an exception. He obviously does not possess the talent of this royal club — he would have been the first to admit as much. Nor did he succeed on the basis of sheer industriousness — he averaged about thirty to forty concerts per and was not exactly known for the athleticism of his shows. But what Buffett was great at — possibly better than anyone to have ever done the job — was scaling through a combination of vertical integration and unbeatable customer service. Jimmy Buffett gave fans exactly what they wanted, then found out what else they wanted, and then he gave them that as well.
This ascent from aging semi-star to business mogul, occurred largely between 1989 and 1994 — a period in which Buffett released no new albums. “Off to See the Lizard,” from 1989 was a modest seller with one very minor Adult Contemporary hit (“Take Another Road”) released by a fledgling entrepreneur. However, by the time of his next album, “Fruitcakes,” released in 1994, Jimmy Buffett was a nearly fifty-year old business mogul, with multiple best-selling books, a booming food and beverage business and a theatrical musical in the works. He was exactly the same guy he was before, just a little less drunk and a lot richer.
If the previous version of Jimmy Buffett was a briney, fun loving troubadour, this new version was that guy, with an additional air of Wall Street savvy. His persona had become a brand. Which meant that, if ever there was a time for Jimmy Buffett to take a major musical risk, 1994 — when he had an empire to build and a brand to scale — was not that time. Having been away from the world of music for half a decade — a period wherein Hip Hop went mainstream and Rock and Roll got weird — Buffett could have tried something new. Something more modern. Something more alternative or electronic. Graciously — for fans, critics and shareholders — he did nothing of the sort.
“Fruitcakes,” Buffett’s eighteenth studio album, was both his first to reach the top five on the sales charts as well as his first Platinum-seller since the 1970s. Its title is a nod to fans — those sun loving, clothing optional weirdos who sometimes get drunk and say silly things but who possess a positively essential joie de vivre. It almost goes without saying that most Parrotheads are not clothing optional weirdos. But it’s also worth saying that many of the teachers, lawyers and middle-managers that comprise his fanbase do fantasize about being carefree, clothes-free beach dwellers. And that is precisely Buffett’s appeal — how he taps into a primal need to escape. An urge to — every once in a while — exist in a liminal space between feeling warm and feeling nothing at all.
Buffett achieves this through his uncanny knack for blending steel drums with Country twang, by rewriting Elmore Leornard for the Club Med crowd, and by celebrating life’s gentlest pleasures. That’s always been the Margaritaville formula and on “Fruitcakes” the recipe is untampered with. Unsurprisingly, the album’s best moments are also its most familiar — the fan service slash statement of purpose title track, and the Southern Florida Rocker by way of Havana Calypso of “Everybody’s Got a Cousin in Miami.” And while both songs extend past seven minutes, that space allows Jimmy and The Coral Reef Band to stretch out, sing along, get white boy funky and return to the melodic centers of what are basically nursery rhymes for tipsy adults. It’s not my cup of tea, but it sure is sweet and, moreover, I admire the work that goes into each serving.
The misses include “Lone Palm,” which wants to be either a Bob Seger soul poem or Shell Silverstein on his third Mai Tai (or both), but which winds up being a listless bummer. And then there are the covers — three timeless songs bungled by a singer whose technical skill and emotional range were never his strong suits. Buffett’s rendition of The Dead’s “Uncle Tom’s Band” is boring and unnecessary. His take on “Sunny Afternoon” lacks the bittersweetness of The Kinks. And, most appallingly, his cover of the Patsy Cline classic, “She’s Got You,” is devoid of the feel and phrasing of the original. Two of the three might make acceptable concert filler but none are particularly interesting. And the last of the lot warrants an apology.
One of Buffett’s enduring bugs — which actually plays like a feature for lubricated fans — is his metronomic delivery. All those congas and steel drums are decoration and misdirection for the fact that he is an unerringly steady — some might even say boring — singer. He doesn’t do vocal runs. Not much falsetto. He can get excited — he can even shout a bit. But the passion and the volume are always Key West appropriate. Moreover, he’s the opposite of a “jazzy” singer. He sings exactly “in the pocket” of the rhythm, not before (like Willie Nelson) or after (like Leonard Cohen). As a vocalist, he is formally “mid.” Which is why I was so surprised by “Frenchman for the Night,” a supple, (yes) jazzy, Country ballad about the displacement of touring and the slow, but immutable passage of time. It’s a song one might expect from Willie or k.d. lang or, even, Neil Young. But not from Jimmy Buffett. Amid all the Parrothead “I see you, you see me” fare, it’s a minor moment. But it’s among his loveliest songs and finest performances.
While it broke no new ground, “Fruitcakes” also did not cede any. Which is why — beyond its chart performance — the album was an unmitigated success by standards of Margaritaville Incorporated. As a piece of musical product, it’s firmly a “B.” But, as a soundtrack for Buffett’s roaring third chapter — a quarter century that included a heroic return to Nashville, multiple beachfront homes, mountains of charitable giving and a bottomless array of brand extensions — it successfully validates his unprecedented product market fit.
Like The Dead or Phish or Dave Matthews, Jimmy Buffett’s success is only partially about the music. It’s the pre-show tailgating, the merchandising, the imbibing, the show itself, the brand and the merchandise that collectively drive the phenomenon. Compared with that trio, Buffett is perhaps the one taken least seriously as a musical artist. No small part of that is his refusal to take himself too seriously. And yet, I find that he is the most literate and self-realized of those jamming “brand bands.” In ways that his fans deeply understand, but also in ways that they probably don’t care all that much about, Buffett has more in common with John Prine than with Jerry Garcia. Buffett is a serious writer obsessed with being unserious. Prine writes about everyday people’s everyday struggles. Buffett, meanwhile, writes about their escapes. Apparently, the former gets you cache among the musical cognoscenti and a place in the Songwriters Hall of Fame while the latter gets you legions of drunk vacationers, a billion dollars and — one day — a chapter in business textbooks.