Brian Kevin/Photo © Katherine Roberts

When you think of Hunter S. Thompson, you probably picture the bald, bespectacled, cigarette-brandishing, gun-toting outlaw, whose own life was only slightly less over-the-top than the gonzo journalism he popularized. But before all the hyperbole and posturing, there was an earnest, inquisitive young writer eager for a break. At the age of twenty-five, Thompson spent a year traveling in South America and selling stories about the region’s political and social struggles to a newspaper back in the States. Fifty years later, travel writer and Thompson fan Brian Kevin traced the writer’s route, investigating what became of the places Thompson wrote about, and what he discovered on his trip that caused him to declare, at journey’s end, “I now understand the United States, and why it will never be what it could have been, or at least tried to be.” Kevin chronicles that experience in his brand-new book, The Footloose American: Following the Hunter S. Thompson Trail Across South America. Kevin spoke with Biographile about the experience of following in some pretty big footsteps.

BIOGRAPHILE: Which came first, the idea for the trip or the idea for the book?

BRIAN KEVIN: They were sort of one and the same. I had initially read some of Hunter S. Thompson’s letters from South America in The Proud Highway and the intriguing thing is that in any work about Thompson, to the extent they mention his time in South America at all, it’s really footnote-y. He came back from that trip and a little more than a year later he was really embedded in the counterculture. I remember thinking, Man, there has got to be more said about this. I was also in a place where the notion of picking up and going abroad seemed really romantic. I didn’t do it. I was in a relationship that became a marriage and I was in an office job and, in this world, that precluded free-wheeling travel. And close to a decade later I found myself in the exact same spot – only now thirtyish, and so I decided to do it.

BIOG: How much writing did you do on the road?

BK: I did a ton of note taking. I set up some formal interviews, but there wasn’t a lot of writing on the road. My first editor encouraged me to blog, so three times a week I was sitting down and writing a blog that I don’t think anybody read, but it ended up being a good exercise to sit down and have to make meaning out of things every forty-eight hours or so.

BIOG: Was it hard not to be influenced by, and imitate, Thompson’s voice?

BK: It was never my goal to imitate. You emulate writers you admire to one degree or another, and there are definitely parts of this book where I am grabbing techniques of his, but that Thompson voice has been done so badly so many times before, and I think one of the great ironies of him is that he probably engendered just as much bad writing as good writing. People think, Now I can be a hyperbole-spouting crazy nutjob, but there’s so much more to it. He started out doing interesting and good straight journalism; he had a solid background in the old-school techniques of reporting. Then, much later, his style became self-parody, I most certainly did not want to do that. Living the gonzo life and reporting the gonzo way was never on my radar.

BIOG: What other travel books served as models?

BK: I feel like we sometimes shoehorn travel writing into this mold of the personal quest, like, there’s some part of me that’s missing and I’ve got to go find it. But if we turn every time we leave the house into this profound search for meaning, we do so at our peril. I also think women are expected to do that more so than men, which is weird and uncomfortable. I do hope that the finished product maybe feels like a little bit of a throwback to Paul Theroux or Bruce Chatwin, that moment when it was enough to sit down and maneuver your way through a foreign landscape without having to discover something.

BIOG: Hunter S. Thompson said he traveled to South America to understand the failure of the American dream. Did you come to a similar understanding?

BK: I think. Maybe? I came up with my pet theory about what he meant by that. He was traveling during the peak of the Cold War containment era. This notion of modernization theory was motivating American foreign policy, which is this idea that underdeveloped parts of the world will eventually be like us if we tweak them in the right way. So that was the mindset Thompson was coming from, and I think he came to realize that the problems third world nations face are not the kinds of things that evaporate after those places have evolved. I think he looked back to the U.S. and saw that all of those ghosts are with us, too; we haven’t surpassed any of those problems. You see that now in terms of Occupy Wall Street and all these frustrations that are bubbling over.

BIOG: What place seemed the least changed, and where seemed the most?

BK: Thompson writes a lot about mining in Bolivia and how the condition of Bolivian miners is as abject in 1962 as any he’d encountered. He was pretty stunned by that. He talked about the life expectancy of miners being somewhere in the thirties. Sixty years have gone by, and that pretty much still describes resource extraction in Bolivia. The miners are still struck down by silicosis in numbers that are shocking for 2014. In terms of what’s changed the most, in eastern Bolivia, in the plains, Thompson found nothing. There was this giant expanse. He stopped in Santa Cruz, which was basically a frontier town, but they’ve subsequently found natural gas and now it feels like Tomorrowland. He would not recognize Santa Cruz one bit.

BIOG: You write that Thompson’s travel writing gave birth to the gonzo style he is known for, and that at the end of his trip he had stopped taking it all so seriously. Did you have a similar experience?

BK: I don’t think I reached the same “the hell with it” moment that I think Thompson did. I think he gave in to the chaos of it all. Part of it is him saying, I’ve had dysentery for two months, everywhere I go there’s a new uprising that prevents me from reporting, I’m just going to say, what the hell and dive in. People were really generous with their time and knowledge so there was only so much to hell with it I was willing to say. That being said, I had some fun too.

BIOG: How did the trip change you as a writer?

BK: It definitely made me train myself to not treat human beings like they are plot devices simply because they speak another language and live a drastically different life than me. There’s a tension in all travel writing, because you are an absolute rube with regards to your subject, but you’re an insider with regards to your reader. If you lean too far in one direction, then you trivialize the experience of an entire continent of people. The trip made me remember that things happening around me are profoundly more interesting than I am.

BIOG: What do you think Thompson would’ve have thought of your project?

BK: I can’t begin to imagine what Thompson at forty or sixty would’ve said about it. But I think Hunter S. Thompson at twenty-five would’ve been into it. I think if we were having a beer he’d admire what I was doing enough to sit down and lecture me about what I was misunderstanding about the role of the Peace Corps. And I would take that as a compliment. I’m cautiously optimistic that we could sit down and have a good argument.