The Footloose American: Following the Hunter S. Thompson Trail Across South America (2 page)

I read the book shortly thereafter. In its day,
Fear and Loathing in Las Vegas
was a bestseller, published a year after it was serialized in the pages of
Rolling Stone
. At the time, Thompson was a literary up-and-comer, known mostly for his reporting on the popular politics and subcultures of the 1960s, and
Fear and Loathing
was a deranged blend of fact and fiction that made his name. The
New York Times
called it “a custom-crafted study of paranoia, a spew from the 1960s and—in all its hysteria, insolence, insult, and rot—a desperate and important book.” I read it cover to
cover one afternoon, stealing pages between mozzarella-stick deliveries during a slow shift at the Applebee’s where I waited tables.

From the get-go, Thompson’s writing style got its hooks in me—his sense of humor, his exaggerated descriptions, the raw confessional tone with which he describes a fragmenting American society. He famously referred to his work as “gonzo journalism,” and I admired his gall for brazenly branding his own technique, like a boxer or an avantgarde painter. His writing was indeed subversive for its day, blending old-fashioned immersion reporting with literary techniques more reliably found in fiction—tools like scene, dialogue, and point of view that had mostly been the domain of novelists and short-story writers. Critics in the early ’70s referred to this style as “the New Journalism,” and Thompson was considered one of the genre’s standouts, alongside now-canonized writers like Joan Didion, Norman Mailer, and Truman Capote.

Not that his prose style is necessarily what Thompson is remembered for. In the popular consciousness, Thompson’s name and his “gonzo” brand are more immediately associated with the flamboyant drug use and crazed antics that eventually came to complement or cloud his literary reputation, depending on whom you ask. From his early fame as a
Rolling Stone
contributor in the 1970s to his suicide in 2005, he built a pop-culture legacy around his unconcealed fondness for Wild Turkey, cocaine, and LSD. He invited camera crews onto his homestead near Aspen to watch him fire automatic weapons and detonate explosives. In 1970, he ran for Aspen’s county sheriff on the Freak Power ticket. In the ’80s, he was a regular patron and honorary manager at San Francisco’s storied O’Farrell Theatre sex club, and in 1990, police raided his home to seize an apothecary of illegal
drugs, along with several sticks of dynamite. When he shot himself at age sixty-seven, he left behind a madman’s legacy and a note that read, “No More Games. No More Bombs. No More Walking. No More Fun.”

But long before any of that, Thompson was just a twentysomething kid with thirty bucks trying to hitch a ride off of Aruba. Which is why
The Proud Highway
made up the bulk of my carry-on. The book is one of the few pieces of Thompsonalia to pre-date the emergence of the author’s loose-cannon public persona. It’s a collection of letters that Thompson sent in the late ’50s and early ’60s, back when he was just an eager and anonymous young freelancer, and included within are eighteen letters he wrote during a single year spent wandering across South America.

Outside the Barranquilla airport, I reached into my bag to feel for the book, patting it with one hand while I waved down a cab with the other. As I arrived in Colombia, clueless and luggageless, those eighteen letters were the closest thing I had to a guide.

“Goddamn,” said the photographer a few hours later, looking at me from across the table of a Barranquilla pub. “This might not be the ugliest city I’ve ever seen, but it is a
hella
strong contender.”

The two of us were seated in a strip-mall sports bar in a bland commercial stretch of the city. I took a sip from my beer and looked out the window, where a column of beige and boxy office towers hemmed us in. The palms along the road seemed to wither in the evening heat, and my sweat-soaked shirt clung like a cobweb to the back of my vinyl chair. I let the cool bottle linger against my lips, a momentary antidote to the swampy humidity. Beer consumption on this trip was going to be high, I thought.

My drinking companion was photographer Sky Gilbar, a California expat living in Panama and an accomplished Associated Press photographer who’d worked extensively in Latin America—though not so extensively he wasn’t still prone to grating Cali-isms like “hella.” In the weeks after buying my impromptu plane ticket, I had surfed the social networks for some travel advice, and Sky and I were introduced online by a friend of a friend. “Colombia is a stunningly beautiful country,” he wrote in an e-mail, “with the warmest people you are likely to find anywhere on Earth. Did I mention the most beautiful women on the planet?” I was going to have a great trip, Sky assured me, although he wasn’t so sure about my proposed itinerary. Barranquilla, for starters, was nothing but a “hot and bland port city.” Of all the sunny, sexy destinations in Colombia, why would I want to go there?

I asked Sky whether he was familiar with Hunter Thompson. Sure, he said,
Fear and Loathing in Las Vegas
, right? In fact, he was a big fan. So I decided to tell him everything I knew about the Hunter S. Thompson Trail across South America.

It’s not a part of Thompson’s biography that gets much attention, but from May of 1962 to May of 1963, the future “gonzo journalist” was a freelance South American correspondent for a since-defunct newspaper called the
National Observer
. At the time, he was twenty-four years old, still a starving unknown looking to make a name for himself as a writer. He’d been churning out short stories since he was in high school and, for a couple years, doing some small-time freelancing, contributing short, newsy features to papers like the
Louisville Courier-Journal
and the
New York Herald Tribune
. In 1960, he’d spent a few months working in Puerto Rico—a decidedly non-glamorous job at
an English-language bowling magazine—and after returning home broke, he’d started work on a novel about licentious American drifters living in San Juan, called
The Rum Diary
. But Thompson was restless, looking for his big break.

A Kentuckian by upbringing, he was living on the California coast when his South America plan materialized. He’d spent most of 1961 shacked up in the pastoral, bohemian enclave of Big Sur, hunting wild boar, working on the novel, and rubbing shoulders with folks like Henry Miller and Joan Baez. From well-traveled local luminaries like Miller, he’d heard tales of the expat life, and he’d done just enough island-hopping the year before to get a taste of it. His travels in the Caribbean had taken him within a few hundred miles of the South American mainland, and in Thompson’s imagination, the continent was “the last frontier,” an unspoiled outback brimming with untold stories, where the field of freelancers was thin and the biggest story of the era—the Cold War—was playing itself out daily in the streets. In South America, Thompson figured, a hungry reporter could make a name for himself. Such a trip, he wrote in a letter, may be “my last chance to do something big and bad, come to grips with the basic wildness.”

Thompson’s plan happened to coalesce with the launch of the
National Observer
, an upstart newspaper founded in February 1962 by the Dow Jones Corporation. The
Observer
was an early experiment with the concept of a national newspaper, a sort of precursor to
USA Today
. It was a weekly paper aimed at an educated readership, with an emphasis on in-depth reporting and analysis that the quick-turnaround dailies couldn’t match. At around 200,000 readers, its initial circulation was smallish (Dow Jones’s flagship paper, the
Wall Street Journal
, reached nearly 800,000 at the time), but the novelty of a weekly national newspaper
attracted a lot of attention in media circles, so the
Observer
was widely read and discussed among influential writers and editors at other publications.

The fledgling paper was actively seeking contributors, and when Thompson wrote about the prospect of submitting a few articles from South America, the
Observer
’s editors encouraged him to send whatever seemed like a good fit. It was all the invitation that Thompson needed.

“I am going to write massive tomes from South America,” he declared in a letter just three days after the
Observer
’s inaugural issue. “I can hardly wait to get my teeth in it.”

All of this I explained over e-mail to Sky, who wrote back that he’d had no idea Thompson was once a foreign correspondent. This, I said, wasn’t surprising. The year that Thompson spent down south is a period in his life that his biographers have all but ignored. In the years since the author’s death, dozens of “lost interviews,” biographies, and remembrances have offered glimpses of Thompson the man, but most tend to focus on his later career and the eccentric character he came to adopt. To some degree, this neglect of Thompson’s South American reportage is understandable. He is, after all, a writer whose name has become synonymous with the oddities and ugliness of US culture. Thompson famously proclaimed his beat to be “the death of the American dream,” and outside of those few early letters, his own writing rarely mentions his young adventures abroad.

But Thompson’s South American pilgrimage shaped, in no small part, the edgy journalist who came to national attention not long after his return to the States. Before setting out for South America, Thompson was a wannabe novelist and photographer, a post-Beat dilettante more concerned with short stories than social movements. He fervently
identified with Lost Generation writers like Hemingway, Fitzgerald, Faulkner, and Dos Passos, and he often looked down his nose at the grind of workaday journalism, dismissing it as a soul-sucking task to be undertaken only for a paycheck.

The Hunter Thompson that America came to know—the freewheeling correspondent, the caustic social chronicler—
that
Hunter Thompson was born in the streets of Rio de Janeiro, the mountains of Peru, and the black-market outposts of Guajira. It was in South America, in fact, that Thompson developed his razor-edged understanding of the dying American Dream.

“After a year of roaming around down here,” he wrote at the end of his journey, “the main thing I’ve learned is that I now understand the United States, and why it will never be what it could have been, or at least tried to be.”

That line had puzzled me since I first read it in
The Proud Highway
nearly a decade before. Just what did Thompson mean by this? It’s a declaration that stands in stark contrast to another that he made about five months before the trip. In January 1962, Thompson wrote to a friend in Europe, scoffing at the idea that travel might meaningfully alter one’s perspective on the United States.

“I doubt that a man has to go to Europe, or anywhere, for that matter, to understand the important things about this country,” he wrote. “Maybe he has to go to Europe to be prodded into articulating them, or before they seem worth talking about, but I think we have enough space and perspective over here so a man can step off into a corner and get a pretty good view.”

But Thompson found something in South America that dramatically reshaped his views on home—that dramatically
reshaped
him
. The Thompson who left for the continent in 1962 was a self-identified seeker and escapist. The one who came back a year later was a narrow-eyed critic of American political culture and social ritual. If
The Proud Highway
became one of my favorite books as a college student, I think it’s because it offered a tantalizing glimpse at the nomad who came in between, and I wanted to better understand that transition. When I first read it, I was twenty years old and still reeling from my own first exposure to international travel, a relatively tame semester in suburban Scotland. I was gripped by the notion that travel could confer the same eagle-eyed clarity that Thompson seemed to enjoy, and I told myself that I would go abroad again as soon as possible.

But I never did, and ten years later, I found myself still wondering about that act of transformation, about how you could leave home one day and come back with a clearer understanding of your own world and your place in it.

So a couple of months before purchasing my Colombia ticket, I dug up all of Thompson’s South American reportage from a dusty microfiche archive of the
National Observer
. In total, there are eighteen stories. A few were reprinted in Thompson’s 1979 collection,
The Great Shark Hunt
, but most have been out of print for more than fifty years. The majority of the articles revolve around the Cold War drama of American foreign policy, the triumphs and travails of a Kennedy-era idealism that sought to remake South America in its own capitalist image. Others offer “slice of life” portraits of societies colored by corruption, violence, and political intrigue. The stories offer glimmers of the “gonzo” style that Thompson would later develop. They’re gritty and shrewd, and most impressively, they’re keyed into a number of social issues that still affect the continent today.

Reading Thompson’s
Observer
stories and letters from
the continent, I got the impression of a bright and driven young writer—a bit of a hell-raiser, sure, but one with a clear voice and an emerging interest in democracy and world affairs. Thompson the vagabond reporter came off as worldly and inquisitive, with a lightning-quick wit and a budding sense of injustice. It was, in many ways, a template for the sort of writer—for the sort of
person
—I wanted to be. Poring over the columns of old newsprint, my face lit up by the glow of the microfiche reader, I found it impossible not to layer my own voice over Thompson’s, not to feel a sense of kinship. Both of us had come out of flyover country and settled in the American West. We shared a love of the outdoors and a nascent interest in politics. And we were, it seemed to me, both at a similar place in our lives. I too felt the now-or-never urgency that the young Thompson had described, that looming sense of a “last chance to do something big and bad, come to grips with the basic wildness.”