Airman second class Hunter S. Thompson at his desk in 1957 as sports editor of the Command Courier
Hunter S. Thompson was, it could be easily argued, the most talented, unique, and original journalist of the 20th century. The founder of Gonzo journalism, which is a blend of fiction, autobiography, and subjective reporting, his public persona became larger than life and a caricature of himself as he was fictionalized in films and in the famous Doonesbury cartoons, to the extent that when he was invited for speaking engagements, he didn't know what persona he was expected to deliver. However, he lived his life so unusually that caricature was inevitable.
Born in 1937 in Lousiville, Kentucky, Thompson's father died when he was 14, leaving his librarian mother to care for him alone. He was intelligent and creative as a child, and it is unsurprising, given his mother's profession, that he was inspired by books. Among his defining characteristics was a mistrust for authority, evident by his early and lifelong disregard for the law: He saw little reason to trouble himself with legalities and lived his life on his own terms.
Thompson's high-school senior portrait
In high school he joined the school's Athenaeum Literary Association and wrote for their newsletter, becoming known for his wit and sarcasm. He made friends with the rich kids in town because those of his own lower economic class were less interested in books, but he always thought of himself as an outsider. He would hunt and shoot with one group and analyze literature with another, never really becoming part of either.
His affluent friends and he began vandalizing property and drinking, despite being underage, and even committing robberies. Apprehended by the police after he and two friends stole a wallet, they ended up in jail. His friends' parents were able to get their children out, but Hunter did not have the economic advantage of lawyers and his high school graduation was spent in jail rather than at the convocation. It's an event that solidified his distrust of the legal system and contributed to his anti-authoritarianism. Because of Thompson's record with previous infractions, the judge offered him a choice of a prison sentence or military service, and Thompson joined the Air Force in 1956.
His military service was short, largely because his talents did not include willingly taking orders. He wrote for the newspaper at Eglin Air Force Base in Florida, a post he earned by lying about his experience. In a letter to a friend he wrote: "In short, we both know I'm no more qualified for a post like this than I am for the presidency of a theological seminary; but here is one major fact that makes it possible for me to hold this job: The people who hired me didn't bother to check any too closely on my journalistic background."
He embellished his stories with insubordinate and even slanderous material. Colonel W. S. Evans wrote that Thompson, "has consistently written controversial material and leans so strongly to critical editorializing that it was necessary to require that all his writing be thoroughly edited before release ... Airman Thompson extracted from national media releases and added his flair for the innuendo and exaggeration."
"I hate to advocate drugs, alcohol, violence, or insanity to anyone, but they've always worked for me." (Hunter S. Thompson)
Thompson's slanderous claims in print caused so much trouble that he earned an honorable discharge in 1957, having served only one year. His commanding officer wrote, "In summary, this airman, although talented, will not be guided by policy."
Thompson and Pipe Smoking
It was during this period that Thompson most smoked pipes, though that would later change to his signature long cigarette holders and mostly Dunhill cigarettes, along with cigars. In The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967 (1997), a series of his letters during that time span, Thompson mentions his pipes several times, such as, "Feeling a fit of nostalgia coming on, I hurriedly lit up my charred but tasty pipe." In another instance he wrote:
I got up about ten, fed the dog, took a bath, and had a huge breakfast while I read The New York Times for news of the end of the world. I then took the dog, my pipe, and a bottle of wine and walked about a hundred yards down the hill to the river, where I spent two hours sitting on a huge rock above the rapids, smoking, sipping the wine, and planning a short story.
In another letter he describes a typical morning:
Eat in Old San Juan at six-thirty, out to pick up mail in Rio Piedras at nine. Read your letter on way over here, take off clothes and go naked down to beach with pipe and glass of brandy. Smoke pipe, drink brandy, swim, come back in for shower and to write this letter.
He mentions his pipe in yet another letter: "I keep applying for jobs and people keep running me out of offices because of my hair and my pipe-thing." The subject of pipe smoking arises again when Thompson relates his attendance at an auto show featuring the famous triple-Olympic skier Jean-Claude Killy:
Meanwhile, slumped in a folding chair near the Killy exhibit, smoking a pipe and brooding ... I am suddenly confronted by three young boys wearing Bass Weejuns and Pendleton shirts, junior-high types, and one of them asks me: "Are you Jean-Claude Killy?"
... "Well," I said finally, "I'm just sitting here smoking marijuana." I held up my pipe. "This is what makes me ski so fast."
They stared at me — waiting for a laugh, I think — then backed away. Five minutes later I looked up and found them still watching me, huddled about 20 feet away behind the sky-blue Z-28 Chevy on its slow-moving turn-table. I waved my pipe at them ... but they didn't wave back.
He wasn't actually smoking marijuana at that event, though it wouldn't have been uncharacteristic later. He just liked messing with people. He mentions his pipe again in a letter to someone named Mrs. Boyle: "Thanks for sending the Styron Report; I read it and actually considered, for the first time, that perhaps I might drop the habit. Which really shouldn't be too hard, with a pipe and cigars in reserve. Odd, how language can convince a man, where reason fails entirely."
E. Jean Carroll, in Hunter: The Strange and Savage Life of Hunter S. Thompson (1993), quotes Thompson about his earlier pipe smoking:
We all joined the Sunday school class because we could, ahhhh, we had special activities. At night we had all taken up smoking pipes. We would go to the Walgreen's drugstore across from the library. And we got pipes of tobacco. And sneaked out of the Sunday school and smoked our pipes on the stairs of the church.
Carroll goes on to describe a visit with Thompson:
I went down on spring vacation and visited Hunter in New York after he'd been up to see me at Yale. He was in a very bleak apartment in Greenwich Village, with absolutely no food except a jar of peanut butter.
He smoked a pipe. Wore a long overcoat buttoned up to his neck. And he was thin. I think he was enjoying New York, from an impoverished point of view. He drove this old car and parked it with impunity wherever he wished. And wherever he parked the car he'd get a ticket. And he'd just slide that ticket into the glove compartment. At one point I think he had a hundred and twenty-two tickets. I mean the glove compartment was jammed with parking tickets.
In Outlaw Journalist (2008), by William McKeen, Thompson's pipe is again described as part of his persona: "Gerald Tyrrell was lining up a shot at the pool table of his fraternity house at Yale when he looked up to see Hunter nonchalantly walk into the room, puffing on his pipe."
"If you're going to be crazy, you have to get paid for it or else you're going to be locked up." (Hunter S. Thompson)
McKeen also chronicles Thompson's use of his pipe to impress the opposite sex: "When speaking to women, Hunter could make them feel as if they were the center of his universe. His eyes bore into theirs, and while they spoke, he drew thoughtfully on his pipe, often nodding in agreement with what they said. It was an act, his friends said, and it often worked."
Thompson's pipe was indeed something that he enjoyed in his early years. McKeen records a visit shortly after Thompson lost his newspaper job in the Catskills for vandalizing a candy machine: "The combination bedroom and kitchen made up the other room. The rest of the place was strewn with newspapers, empty beer bottles, and half-downed drinks. He smoked a pipe in those days, so the sweet smell of its tobacco permeated the cabin and drifted out into the fresh air of the Catskill Mountains."
The only reference to a specific brand of pipe found for this article, aside from a Dr. Grabow that Thompson "stuffed with hash," is from When the Going Gets Weird (1993) by Peter O. Witmer: "He wore his normal uniform for that time period — coat and tie, Kaywoodie Briar pipe."
However, as Thompson's life progressed, he seems to have drifted away from his pipe smoking, though never giving it up entirely. He loved tobacco, whether in cigarettes, cigars, or in pipes.
The Writings of Hunter S. Thompson
Self-portrait photo of Thompson c. 1960–1967
Although he was a talented writer even in high school, Thompson struggled to find his own style at first, though becoming a writer seems always to have been his plan. He famously said, "I have no taste for either poverty or honest labor, so writing is the only recourse left for me." He enthusiastically admired F. Scott Fitzgerald and Ernest Hemingway, and to get a feel for their rhythms and styles, he copied The Great Gatsby and A Farewell to Arms over and over on his manual typewriter so that he could experience putting their words and phrasings, sentence structures and imagery on paper. He was determined to achieve his own style but with the skills of great writers.
Perhaps because he was inherently unable to keep a job, Thompson's writing life was spent as a freelancer, at first making approximately $100 per article. He spent a year working in Rio de Janeiro and then returned to the States, marrying his first wife and moving to Aspen, Colorado. While writing about the death of his hero, Ernest Hemingway in 1964, Thompson stole a trophy skull and antlers from Hemingway's home as a souvenir. His assessment of right and wrong was unusual.
His first famous assignment came from the publication, The Nation, to investigate and write about the motorcycle gang, the Hells Angels. Many investigative journalists had declined this assignment because of the danger, but Thompson was perfectly willing and fit in well with the gang's anti-authority philosophy. He spent a year embedded with the Hells Angels until one night when a member started beating his own wife in a bar. His dog bit him during the attack, and he began beating the dog as well. Thompson stood up to the biker, saying, "Only a punk beats his wife and dog." For his intervention, Thompson was himself beaten almost senseless by several gang members, his face swollen and several ribs broken. The beating was probably exacerbated by a rising discontent in the gang concerning Thompson's profiting on the group with his articles. They had demanded half of his proceeds. He decided that he'd had enough of the Hells Angels. "I was finished," he wrote. "There could be no going back now."
Perhaps not coincidentally, Thompson then started collecting and regularly shooting firearms, which seems a rational step when the most violent motorcycle gang in the country hates you. His love for firearms would follow him for the rest of his life. He enjoyed dynamite, too, and would become famous for blowing things up.
The book from that assignment hit the New York Times best-seller list, and Thompson's career flourished. He used his $15,000 advance payment to purchase a ranch in Aspen, which he called Owl Farm. The ranch became the source of explosions and daily gun practice from the time he and his wife moved in and for the rest of his life.
Thompson's 1971 trip to Las Vegas with Oscar Zeta Acosta
On assignment for Scanlon's Monthly, Thompson met illustrator Ralph Steadman, who introduced him to psychedelics, and Thompson's lifelong obsession with drugs began. The two were assigned to cover the 1970 Kentucky Derby and their hallucinogenic experience became Thompson's article, "The Kentucky Derby is Decadent and Depraved." A colleague characterized the article: "That piece was totally gonzo." Thompson thought the article unfit and swore never to do drugs before writing again, but when calls and letters praising it began flooding in he changed his mind and drugs became part of his process. He christened his unique brand of writing, "Gonzo Journalism," essentially an ongoing experiment in which the writer is the central protagonist and active participant in the partially fictional narrative. He later said, "I hate to advocate drugs, alcohol, violence, or insanity to anyone, but they've always worked for me."
"We cannot expect people to have respect for law and order until we teach respect to those we have entrusted to enforce those laws." (Hunter S. Thompson)
His most famous book, Fear and Loathing in Las Vegas, continued his drug-induced composition style and became enormously popular. It started with an assignment to cover a motorcycle race in Las Vegas and became a psychedelic search for the American Dream. The resulting book's popularity seemed to indicate that Thompson's wild lifestyle was necessary for success.
Thompson and Politics
Thompson's dislike for politics and especially for the police was well known. In 1968 he witnessed the beatings of protesters at the Democratic National Convention and wrote that the brutality shown by the police was 10 times worse than anything he witnessed in The Hell's Angels. His contempt for police is perhaps most shockingly demonstrated in his quote, "Grafitti is beautiful, like a brick in the face of a cop."
"Freedom is something that dies unless it's used." (Hunter S. Thompson)
That attitude helped motivate him to run for Sheriff of Pitkin County, Colorado, in 1970. He had written an article about recent elections in Aspen called "The Battle of Aspen," which made him very popular in his hometown. Campaigning on limiting the clearing of trees to make room for tourist vacation homes in Aspen as well as for the legalization of marijuana in Colorado, his campaign poster featured an illustration of a raised fist with two thumbs in a star with a peyote button in its palm, which became known as the Gonzo Fist. He came very close to winning the election, defeated only by one of his opponents dropping out to consolidate the votes against him.
Politics continued as a theme for Thompson in his book, Fear and Loathing on the Campaign Trail '72. He had no desire to become a political journalist and had no fear of burning bridges or insulting politicians and any other witless individuals in the campaigns. He did not have to nurture relationships and protect sources, and his brutal honesty attracted the attention of politicians. He hated Richard Nixon with a fiery passion and said he represented everything that was wrong with the United States.
He considered George McGovern's loss in that election to be another indication of the death of the American Dream. In the next election, he wrote about Jimmy Carter, and it was widely thought that Thompson substantially helped Carter win. Thompson became trusted by people for his no-nonsense assessment of politicians. He broke every rule for political writing and became one of the most memorable political writers in history.
Thompson with George McGovern in San Francisco, June 1972
Thompson in Pop Culture
Thompson was propelled into even wider fame in 1980 with the film, Where the Buffalo Roam, starring Bill Murray and based on Thompson's exploits. He was also the inspiration for the character Uncle Duke in the wildly popular comic strip, Doonesbury, by Garry Trudeau. Famous people like Bob Dylan, Jack Nicholson, and Bill Murray became his friends.
He started attending events in inebriated states, largely because his fame had driven people to expect it. He had become a caricature of himself. "This myth," he said, "is growing and mushrooming and getting more and more warped." His fame drew groupies in multitudes to him and, unable to resist the temptation, he found himself in multiple affairs, destroying his marriage.
Thompson had become such a power as a writer that almost no subject seemed worthy of his talent. Assigned to cover a Mohammed Ali fight, Thompson instead of attending floated naked in his hotel pool, in which he had dumped a pound and a half of marijuana. "What fight?" he said. "Oh, I didn't go to the fight. I stayed in the hotel swimming pool." Even for Thompson, that was inadequate coverage, and he was forced to step away from writing for a while.
Because of his success, he was able to substantially retire. It was in 1997 that filming started for the Johnny Depp film, Fear and Loathing in Las Vegas. Depp wanted to meet and interact with Thompson to better portray him in the film, and the two became friends, with Depp living in Thompson's house for an extended period. He stayed in the basement with a crate of dynamite next to his bed.
"Insanity is a legal term. Crazy is an art form." (Hunter S. Thompson)
They stayed awake many nights to fire guns and blow up dynamite, and they read to each other, with Depp reading Thompson's work and Thompson instructing him on the exact rhythm and emphasis that he preferred. One of the items that Depp read aloud was The Rum Diary, for which Thompson had abandoned publication, but Depp talked him into submitting it and would later star in the film version of that book, released in 2011.
In 2005, Thompson took his own life in the same way as his hero Ernest Hemingway had: by gunshot. He had talked about suicide before and had long planned his own funeral. His wish was for his ashes to be shot out of a fist-shaped cannon, and his friend Johnny Depp made that happen, financing the funeral, which was more of a celebration, with fireworks, music, and partying.
However we view Thompson's life, with approval or disapproval, it cannot be argued that he wasn't an original who lived his life in his own unapologetic way. Troubled and talented, he was among the most successful writers of his time, or of any time. He lived hard right up to the end and finished as he aspired. In Thompson's words, "Life should not be a journey to the grave with the intention of arriving safely in a pretty and well-preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming 'Wow! What a Ride!'"
- "Hunter S. Thompson: From the Florida Panhandle to Infamy," by Sarah O'Bierne.
- "Hunter S. Thompson's Daily Routine Would Kill Most of Us," (2021) by Chris Zappa.
- The Great Shark Hunt, by Hunter S, Thompson (1979)
- The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967(1997), by Hunter S. Thompson
- Hunter: The Strange and Savage Life of Hunter S. Thompson (1993), by E. Jean Carroll
- Outlaw Journalist (2008), by William McKeen
- Fear and Loathing (1993), by Paul Perry
- When the Going Gets Weird (1993) by Peter O. Witmer