Hitchhiking on the Proud Highway: Hunter S. Thompson and an American Past-time

By Jack Reid

Photo from hitchhiking journey west in 1960 (also the cover of the edited volume The Proud Highway)

In 1963, a young Hunter S. Thompson published a thoughtful eulogy to a beloved pastime of his titled, “The Extinct Hitchhiker.”  Thompson had taken a keen interest in hitchhiking five years earlier after reading On the Road as a twenty-one-year-old living in New York City. Although Thompson would come to be known for his famed Gonzo approach to writing with the publication of Fear and Loathing in Las Vegas (1971)—at the time he was an unknown writer struggling to pay his mounting bills.  Even so, this reality did little to diminish his spirit.  Indeed, he was desirous of everything and eager to see the world and all it had to offer. 

Over the next several years Thompson certainly did, chasing down stories throughout the United States and even into the Caribbean and South America.  Still, his memories of hitchhiking adventures years earlier stuck with him, prompting him to circle back to the topic while freelancing for an upstart weekly newspaper called The National Observer.  The resulting article framed hitchhiking as a “lost art,” a bygone form of spontaneous transit out of touch within an increasingly regimented America. What Thompson failed to realize at the time, though, was that hitchhiking was instead on the cusp of a renaissance among young people.

Once common during the Great Depression and World War II years when a sense of national crisis forged a more cooperative civic culture in the United States, hitchhiking began to lose popularity in the 1950s as the country’s citizenry became increasingly prosperous and risk-averse.  With more Americans than ever able to afford automobiles, many critics characterized flagging down a stranger for a ride as anachronistic and needlessly dangerous. Yet a series of historical circumstances, including the publication of Jack Kerouac’s On the Road in 1957, helped the practice to gain traction among growing numbers of middle class, white youths. 

Kerouac’s romanticized portrait of the road and the characters who populated it gave restless mobility a hip allure to a generation of young men yearning to cast off the comforts and predictability of post-war suburbia.  By the late-sixties, women too began to see hitchhiking as a vehicle toward a more liberated sense of self.  Some youths hitched across town, while more ambitious individuals took off on extended journeys throughout the country.  Surviving the difficulties of a rucksack existence on the open road and meeting a cross section of Americans they would otherwise likely never meet opened their eyes to a new world.  As Thompson’s writing career took off in the early 1970s, so too did the popularity of hitchhiking, which thrived as a form of alternative transit until the late 1970s.

Born in Louisville, Kentucky, Thompson moved to New York City following a bumpy stint in the Air Force that came to an end in 1958While living in New York, he wrote constantly.  Although finding steady work as a journalist, he ultimately wanted to become a novelist in the vein of his hero Ernest Hemingway.  Thompson was drawn to the literary output of those he described as “men of action,” individuals who in his mind captured the essence of masculine individualism and intellectual vigor.

“At age 22, I set what I insist is an all-time record for distance hitchhiking in Bermuda shorts: 3,700 miles in three weeks.”

This sentiment and the growing popularity of the beat movement led him to read On the Road once he arrived in New York.  Impressed, he wrote to a friend “I’m beginning to see what Kerouac means when he says ‘I want God to show me his face’: it is not the statement, but what the statement implies: ‘I want to believe in something.’” In an earnest but irreverent tone, he observed “the man is more of a ‘spokesman’ than most people think…and he speaks for more than thieves, hopheads, and whores.”[1]  Still, he wasn’t completely sold on Kerouac, complaining to a close friend that most of his other works were vastly inferior to On the Road.  With an early taste of the ruthless wit that would soon become a trademark of his, he noted “The man is an ass, a mystic boob with intellectual myopia.”[2]

Regardless, On the Road left an imprint on Thompson and many other young people at the time. In August of 1958 Thompson embarked on a hitchhiking trip around the country—hoping that an unfiltered dose of the human condition would inspire the great American novel he was aching to write.  He took off once again in the autumn of 1960, hitchhiking with a friend from New York to Seattle, before heading over to San Francisco.  The two were ostensibly looking for work, but the frequent photos of themselves posing on the roadside sporting a beat disposition suggests that they imagined the trip in more romanticized terms as well.[3]

In his 1963 article, Thompson looked back on those hitchhiking days, remarking “Can any bus, plane, or train match the feeling of standing out on a morning road with the sunlight in your face and the smell of new-cut grass all around and no worry in the world except how far the next ride will take you.”  Still, Thompson was too impatient to take in such a moment for too long.  In the same article, he bragged “At age 22, I set what I insist is an all-time record for distance hitchhiking in Bermuda shorts: 3,700 miles in three weeks.”[4] 

Although Thompson believed the practice was on its way to extinction, a number of historical circumstances in the mid-to-late 1960s inspired a growing number of youths to share his enthusiasm for hitchhiking.   While a generation of adults who had survived the Great Depression and World War II wanted comfort and predictability, many of their children looked to escape these staid environments.

In the end, thrifty transit made hitchhiking practical and appealing, but it was the wild stories that came out of these spontaneous experiences that gave the practice hip cache among young people. In the case of Hunter S. Thompson, hitchhiking offered an antidote to his restlessness and a vehicle to vigorously grab life with both hands. Thompson famously wrote “Buy the ticket. Take the ride.”  In this case, the ride was free.  Ultimately, this instinct to live with a boldness and intensity beyond what most could handle would fuel the rest of his writing career and life more broadly.

Jack Reid is a historian of American culture and the author of Roadside Americans: The Rise and Fall of Hitchhiking in a Changing Nation (University of North Carolina Press, 2020).

[1] Hunter S. Thompson The Proud Highway: The Saga of a Desperate Southern Gentleman, ed. Douglas Brinkley (New York: Villard Books, 1997), 110

[2] Thompson, The Proud Highway, 140.

[3] For instance, see Gonzo, ed. Steve Crist and Paul Norton (Los Angeles: Ammo Books, 2007), 19-27.

[4] Crist, Gonzo, 19-27.

Published by annie moye

"The days are gods." — Emerson

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