The Overseas Highway is a 113-mile roadway that stretches across the Florida Keys archipelago, connecting Key West to the US mainland. Along the way there are 42 bridges, the longest of which is just under seven miles. The highway is part of U.S. Route 1, which runs 2,369 miles between Key West and Maine, making it the longest north–south highway in the country. The southern terminus of U.S. Route 1 is located on Whitehead St. in Key West, and marked by signs that read END 1 and MILE 0. As you drive south on U.S. Route 1 the numbers on the mile markers get smaller and smaller, a countdown of sorts.
By the time Zoe and I started down the Overseas Highway, we had been living a nomadic lifestyle out of our 1995 Corolla for nearly four months. We happened to be arriving on the day after the last night of Fantasy Fest, an annual street festival that lasts about a week and often draws over 100,000 people—nearly three times the regular population of the island. Fantasy Fest is like Mardi Gras in New Orleans in terms of debauchery, but differs culturally in that it lacks any sort of religious antecedent; It was invented by a couple of businessmen in the 1970s as a way to drum up tourism in October.
As we drove south towards Key West, the north-bound traffic in the opposite lane was at a near standstill for the entire 113-mile drive. It felt as if we were driving toward some great catastrophe that the rest of the population was fleeing. As others waited in frustration, we made our way south with tropical ease, cruising across the low slung islands—geological artifacts of an ancient coral reef—and the bridges that connect them. We marveled at the perfectly clear blue sky above us and the gem-like sea below, a natural tableau so brilliant it seemed unreal, like we were driving inside a hi-res screensaver.
We were going to Key West because we were nearly out of money. Through a convoluted mom’s–friend’s–husband’s–brother-in-law connection, we thought we had jobs lined up at the Southernmost Hotel and Resort, which, in theory, would have come with living arrangements in addition to wages. This, of course, never panned out.
The chorus to the first song on Jimmy Buffett’s fourth studio album, A1A, goes like this:
I know that this may sound funny
But money don't mean nothin' to me
I won't make my music for money, no
I'm gonna make my music for me
Perhaps it’s the hindsight of knowing that Buffett’s income in 2015 was estimated at $36 million, but yes, it does indeed sound funny. In the introduction to The Jimmy Buffett Scrapbook (3rd Ed.), a garish oversized novelty publication that reads like a 240-page full-color advertisement for Jimmy Buffett’s lifestyle brand, Mark Humphrey writes:
His life, more than that of many performers, is an open book, one whose theme obviously is the enjoyment of life. We have rewarded his enthusiasm by making Buffett wealthy, a man with many toys. The more he feeds our fantasy—“Growing Older but Not Up”—the richer we make him. The richer we make him, the more Buffett beams his beatific smile our way.
The Buffett empire, in other words, has become a sort of thing that feeds itself. A feedback loop where the fan culture’s appetite for consumption fantasy fuels Buffett’s own performance of fantastic consumption. A1A, however, was recorded in 1974, preceding “Margaritaville” by three years, and the launch of his lifestyle brand by nearly a decade. So, it’s a bit easier to buy in to the idea that the song’s protagonist—pre-Margaritaville Buffett—was in fact a sort of beach-bum-cum-busker, another burnout prankster leftover from the 1960s, eeking out an existence at the literal end of the road.
I married a writer whose writing often takes the form of handwritten journals. One of the big ideas I’m trying to flesh out in the process of writing about records and tapes, rests on the fact that music is an artform dependent on time. Without time, music cannot exist. Time is music’s substrate. Thus, music is intrinsically ephemeral, eternally fleeting, impossible to grasp. Analog mediums, however, are manifestations of music as a physical form. They move through space as physical objects. You can hold them in your hands. Zoe’s journals have a similar continuity. They move from one place to another. You can hold them in your hands. They were there, now they are here.
When we got to Key West, the first order of business was to find a place to sleep. There are no campgrounds on the island, we didn’t know anyone living there, and hotels were prohibitively expensive, so we ended up finding a short-term rental in a small, one-room pool house on a part of the island called Old Town.
Imagine a 1950s Hollywood soundstage dressed to look like old Havana, and you probably have a good idea of what Old Town looks like: narrow streets; clapboard houses painted the colors of Easter eggs; low picket fences framing yards of impossibly lush tropical flora—gigantic fragrant blossoms of thick, lingual petals, and prehistoric palms that shed their husky fronds onto the sidewalk below. Also, there are feral chickens everywhere.
The pool house we rented was a tiny outbuilding in the backyard of a larger complex that housed several apartments. It was a box, just big enough for a double bed and an armoire. There was no dedicated bathroom or kitchen. Instead, for bathroom/kitchen needs, we had to walk across the backyard and enter a separate apartment that was occupied by Gary, the 40-something, ponytailed apartment manager from Upstate New York, and Russell, a severe alcoholic.
Here is a transcription from one of Zoe’s hand-written journals:
Before we got here I kept seeing craigslist ads - for jobs and apartments - with a ubiquitous “no drunks” tacked onto the end. I’m beginning to understand why. I guess Russell was in a bad car accident a while back and the drinking has gotten much worse since then. He rides a bike to work and drinks on the job ... Russell lost his wallet during Fantasy Fest last weekend and now he can’t pay rent ... Gary has told him he’s got to go ... This morning there was a typed note on the counter: Maybe God put me here for a reason, you’re the only one that can help me, I start AA this afternoon.
Jean Baudrillard begins the first essay in his seminal book Simulations (1983) with an allusion to a very short Borges story called “On Exactitude in Science.” The story—which is only one paragraph long—is set in a fictional empire, and centers around a zealous cartographers’ guild that is so exacting in their pursuit of accurate mapmaking that they create a map that covers the empire completely, a perfect replica of the territory, overlain on the territory itself. Later generations find the map useless, and ultimately let it wither away, leaving tattered ruins in the desert as its only remains.
Baudrillard sees this story as a useful allegory to our contemporary lived experience, with one major inversion: instead of the real world preceding the simulated world, “it is the map that precedes the territory.” Modernity (or postmodernity) is an epoch in which we have built maps upon maps. The “real” no longer exists. Whereas in Borges’s story the map is a simulation with a clear referent, a “second-order simulacrum,” our world is a simulation of a simulation, the creation of a real “without origin or reality: a hyperreal.”
OK, perhaps Baudrillard is a bit obtuse. Let’s try a thought experiment. Here is an interactive map of a part of Key West that I came to know quite well. Have a look around:
It seems our digital cartographers have surpassed even those of Borges’s Empire. What you have just experienced is a simulation of reality, a copy, what Baudrillard would call (I think) second-order simulacra. So we’re halfway there. Now let’s imagine that some impossibly wealthy oligarch has decided to build a manmade island off the coast of Dubai, and wants you to design it in the spirit of Key West, not an exact copy, but something that evokes the milieu of Old Town. Now let’s say that all you have to go off is the Google Maps simulation that I have just provided.
Now let’s say it’s built. Imagine you’re there, standing on this dredged up island, its narrow streets studded with manufactured cobblestone, its palm trees imported from the Caribbean, the clapboard siding of the buildings you designed artificially distressed. And there you have it, a simulation of a simulation. The map has preceded the territory. We have entered the third-order simulacra, the real from the unreal: the hyperreal.
But of course our thought experiment fails in one fundamental way: it assumes that Key West is real. Yes, it is a geographical place. Yes, you can drive there, or fly there, or take a cruise ship there. You can book a room at The Southernmost Hotel and Resort. You can order local pink shrimp tacos and a 24-ounce margarita at the restaurant where I once waited tables. You can purchase a souvenir conch shell at the gift shop where Zoe once priced and folded T-shirts. You can take a leisurely sunset walk on a beautiful sandy beach. But consider the following:
The airport where your plane landed is on part of the island that was manmade—dredged up and paved over. The shrimp tacos you ate—purportedly Key West’s famous indigenous pink shrimp—were, in fact, farmed shrimp imported from Vietnam. The margarita you drank wasn’t technically a margarita (Key West has a convoluted liquor licensing system that makes it prohibitively expensive for many restaurants to serve liquor; the “margaritas” I served as a waiter were made with agave wine instead of tequila). The conch—a symbol so embedded in the identity of Key West that locals are called Conchs and the archipelago is nicknamed The Conch Republic—is a protected species and therefore illegal to harvest domestically, which is to say your souvenir Key West conch shell was actually imported from elsewhere in the Caribbean. Even the sand beneath your feet is not what it appears to be—the beaches of Key West are not naturally sandy, so to accommodate the popular preference, sand is imported at great expense from the Bahamas, shipped over by barge.
Consider Jimmy Buffett’s anthem “Margaritaville”:
I blew out my flip flop,
Stepped on a pop top;
Cut my heel, had to cruise on back home.
But there's booze in the blender,
And soon it will render
That frozen concoction that helps me hang on.
It’s a drinking song. Country music has a long tradition of drinking songs. The best are, like a proper cocktail, both bitter and sweet. One of my favorites is Webb Pierce’s 1953 hit “There Stands the Glass.” Like “Margaritaville” the song is an ode to the heart’s oldest analgesic:
There stands the glass
That will ease all my pain
That will settle my brain
It's my first one today
But instead of searching for his “lost shaker of salt,” the protagonist laments lost love:
I'm wondering where you are tonight
I'm wondering if you are all right
I wonder if you think of me
In my misery
The difference between Jimmy Buffett and Webb Pierce is that Buffett doesn’t write Country Western, he writes Gulf Western. There is no deep well of sadness, only steel drums and saccharine melodies. Songs like “Margaritaville” are innocuous in the way that contemporary Christian music is innocuous. Even as an atheist, I can find something beautiful and transcendent about the Christian idea of Grace, about the contrast of God’s benevolence in the face of humanity’s misery and failure. In fact, I have a handful of gospel 45s that capture the transcendence of this idea, that point poetically to the experience of divine revelation while singing from the depths of anguish and pain. Yet most contemporary Christian music tries to show light without dark, and in doing so reveals nothing. The result is a simulacrum of meaningful art; think commercial radio jingles, think the theme song to Barney & Friends, think music played in department stores in December, think Jimmy Buffett.
But still, Buffett’s popular song “A Pirate Looks at 40,” somehow got stuck in my head. Of all the music I passively absorbed working in the service industry in Key West, this song was the one that sublimated into my mind and would occasionally bubble up to the surface of my consciousness even after I left the island. There is something bittersweet about the melody. There is even an air of mortality to the lyrics. It became an itch I wanted to scratch. So when I found a clean copy of A1A at a Salvation Army in Seattle, I decided it was worth owning.
“A Pirate Looks at 40” is, according to The Jimmy Buffett Scrapbook, about a Key West drug smuggler named Phil Clark. According to a 1977 interview with Rolling Stone, Buffett himself dabbled in coastal drug trafficking prior to breaking into the music industry: “If I hadn’t gotten into rock and roll seriously, I’d still be out there smuggling my ass off, because I was good at it, the few times I did it. I thought, yeah, I am livin’ my life as a song.”
The real life of Phil Clark came to an end in the Pacific Ocean. After evading arrest in Florida, he somehow ended up in California. He drowned in Sausalito Bay after falling off a boat. “Probably got drunk or something,” posits Chris Robinson, a bartender and former Buffett compatriot. His cremains were eventually returned to Key West, where they were taken on a sort of bar crawl, during which they were snorted, doused in Johnny Walker Black, and ultimately committed to the calm waters of the Gulf of Mexico.
I quit drinking for a month over the summer. In general, I drink too much, and have been drinking too much for the last ten years of my life. One of my takeaways from a month of sobriety was simply this: it’s nice to scratch an itch. It’s nice to desire something. As a species, we have a great capacity for desire, nuanced and complex wants that are beyond our basic survival instincts. We have a word for this capacity: appetite—from the latin appetere, meaning to seek after. It is no wonder, then, that before a meal, the French custom is not to wish you good nourishment or good digestion, but rather bon appetit.
Key West is a land of appetites. It is a simulacrum, built on a specific middle-class American appetite for tropical vacation. For Baudrillard, the American appetite for vacation provided a key insight into his theory, specifically in the case of Disneyland. Disneyland, Baudrillard posited, is no more unreal than anything else. On the contrary it is hyperreal. It is like our lived reality, just heightened. Disneyland exaggerates its artificiality so that when we leave, we are fooled into thinking—by way of contrast—that the world we return to is somehow not artificial.
Key West, I think, has a similar role. It is to show us the difference between regular life and a life of leisure. From the Latin licere, leisure literally means to be allowed. In Key West, we are allowed to drink all day, to be drunk in public, to drink on the streets. We are allowed to live our fantasies in perfect weather, on perfect beaches. We are allowed the sweet without the bitter. Thus we have hyperleisure, and hyperleisure is commodified and exported to the mainland, branded with Jimmy Buffett’s signature, scrawled across the top of the logo.
I have two memories of Russell that have crystallized in mind. In the first, I am sitting outside by the pool that separated the tiny pool house that I rented and the main house where Russell lived. It is early in the afternoon and I am eating candied ginger. Russell wakes from a nap, walks outside into the bright day, and joins me at the table. He asks what I am eating, so I tell him and offer him a piece. As he reaches for the candy, his hand shakes so violently he can’t even complete the simple task. I have to take one from the bag myself and drop it into his palm. I’ve never seen anything like it, a body so physically dependent on alcohol. From this point on I think about him differently. From here on, he is somehow more real.
In the second memory, the “meeting of the minds” is taking place in Key West, an ironically titled annual event put on by Parrot Heads in Paradise, Inc., a not-for-profit that aims to “provide a variety of social activities for people who are interested in the music of Jimmy Buffett and the tropical lifestyle he personifies.” It is evening and Russell is functionally drunk, in one of his better moods. He is holding a long necklace of plastic mardi gras beads adorned with big red parrots. We make small talk and then he says, “Well, I’m gonna’ go see what those Parrot Heads are up to.” He puts the necklace on and leaves, taking a vodka-spiked can of Arizona Iced Tea with him into the balmy tropical night.
What is and was so striking to me—the reason why this memory is so vivid—is that there was a sort of magic in Russell’s necklace. I knew his problems. I knew he was broke and about to be evicted. I knew he drank so much cheap vodka that his hands shook uncontrollably upon waking from a nap. But when he put that necklace on, he became just another reveler. Another consumer of hyperleisure, living the tropical dream, a character in a song, living the tropical lifestyle Jimmy Buffett personifies.
There is a voice in my head that tells me that Jimmy Buffett provides real pleasure for human beings, and that the subculture surrounding him provides a venue for individuals to make real human connections, to feel like they are part of a larger whole. This is not nothing. Then again, you could probably make the same argument about Donald Trump rallies. (It is worth noting that I am making final revisions to this essay on 11/9/2016, the day after Trump’s electoral college victory. But I digress.)
On my last night in Key West, Zoe and I were drinking at a bar called the Green Parrot. The bartender was a casual acquaintance, a guy originally from Illinois named Beaver, who liked the fact that I was from Wisconsin, the state where he had lost his virginity. When I got to the Green Parrot that night, Beaver introduced me to a man who looked to be in his fifties, who was also from Wisconsin.
“Where in Wisconsin?” the fiftyish man asked me after Beaver made our introductions.
“Milwaukee,” I replied.
“Where in Milwaukee?”
“The East Side.”
“Where on the East Side?”
“Shorewood,” I replied.
“Where in Shorewood?”
“Menlo,” I said.
“Where on Menlo?”
“Menlo and Maryland.”
Miraculously, it turned out that we had grown up on the same street. He knew the house I grew up in, even told me the names of the people who had lived in it when he was a child. We talked about the neighborhood, about the the annual Fourth of July parade, about some of the older people who had lived on Menlo long enough to be present for both of our childhoods.
He told me about how his mother used to drive down to Illinois to purchase margarine in bulk and then distribute it to the other women on the block. (Wisconsin, as a direct result of the dairy lobby, had banned the sale of margarine, creating a cottage industry for people willing to illegally import it from neighboring states. My grandmother used to do the same thing.) He then made a joke about how his mother shouldn’t have been surprised, then, when he ended up in Florida driving “fast boats,” i.e., smuggling drugs.
And so, on my last night in Key West, I found myself drinking with a former drug smuggler who happened to have been from the exact place where I was from. He told me a few Key West stories, but mainly he told stories from his childhood. His recollection of names and anecdotes was uncanny. At some point I’m sure I wondered what was true and what was myth. But I had felt like a stranger in Key West for so long, and the improbability of the whole thing was too much, so I gave in and allowed myself to believe. I imagined the end of the road as the beginning—mile 0—and I imagined that road leading me home.