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The Beat Generation, Gonzo Journalism, and Crap Writing

A discussion of the impact of the Beat Generation and Gonzo Journalism on poor writing.

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HST & the Music of the Sixties

Hunter S. Thompson painting

(c)Illustration Isaac Bonan

From Beatdom #7.

by David S. Wills

Music has always been a matter of Energy to me, a question of Fuel. Sentimental people will call it Inspiration, but what they really mean is Fuel.

Music is a theme that crops up throughout the entirety of Hunter S. Thompson’s bibliography. It was an incredibly important aspect of his life, and he always took the time to listen to what he wanted. Those who know about Thompson know that Bob Dylan was one of his heroes, and it is often claimed his favourite song of all time was “Mr. Tambourine Man.” But, of course, there was more. Thompson’s interests were diverse. As a teenager he loved Bing Crosby, whose “Galway Bay” was once his favourite song. He tended to gravitate towards music that reflected the world around him – from Kentucky bluegrass to San Francisco rock ‘n’ roll.

Thompson’s times were wild ones. He lived through the 1960s and 70s, fully immersed in the counterculture of the era. He lived in the Haight-Ashbury during the Summer of Love and watched the musicians of his generation artfully reflect their environment, like he was doing with his writing.

Indeed, Thompson respected their work as much as that of any contemporary writer. He once said, “I’ve been arguing for years now that music is the New Literature, that Dylan is the 1960s’ answer to Hemingway.”

Music was fuel for him, too. Not only did he respect these artists as fellow documenters of the world, but they meant something to him. Good music drove him onwards. It helped him write. And he loved those bands and did what he could to push their careers forward.

As Douglas Brinkley puts it,

He would do anything for the music he liked – people like Warren Zevon, Willie Nelson, Bob Dylan, Lyle Lovett, Townes Van Zandt, Jerry Jeff Walker; old Kentucky bluegrass masters like the Stanley Brothers, Bill Monroe, Earl Scruggs, and Lester Flatt; and some blues people like Howlin’ Wolf and Willie Dizon. Those were gods to him, and a lot of them were friends. He would do anything to promote their CDs, to go to their concerts, to talk them up. But his interest in rock music was not as deep as people think. Because he wrote for Rolling Stone, people sometimes think he was a big music guy. Hunter was not up on current music and didn’t really care to be. He knew what he liked: some Bruce Springsteen; Van Morrison could really get him writing. He knew Leonard Cohen songs by heart. But it was Dylan first and foremost. Any of the Dylan live bootlegs he thought was the greatest thing of all time.”

The above note is telling, but far from complete. Thompson’s favourites spanned decades and genres. He loved folk and bluegrass, but also the various forms of rock music. He was discerning, too. In Jann Wenner and Corey Seymour’s Gonzo: The Life of Hunter S. Thompson, Brinkley also talks about Thompson refusing to sell quotes from his writing to bands that he didn’t like. In his later years musicians would approach him and what mattered was whether or not he liked their style – not how much they were willing to pay. That is telling for a man whose life was spent chasing paycheques and fighting expenses.

In 1970, Thompson took the time to compose a list of his favourite music of the 1960s (which he posed as “Raoul Duke’s” favourite music) in a letter to his editors at Rolling Stone. The list might be surprising for readers of his work. (It should also be noted that two of these albums weren’t even released during the 1960s!)

1)      Herbie Mann’s 1969 Memphis Underground

2)      Bob Dylan’s 1965 Bringing It All Back Home (especially noted as “Mr. Tambourine Man” in his letter)

3)      Dylan’s 1965 Highway 61 Revisited

4)      The Grateful Dead’s 1970 Workingman’s Dead

5)      The Rolling Stones’ 1969 Let it Bleed

6)      Buffalo Springfield’s 1967 Buffalo Springfield

7)      Jefferson Airplane’s 1967 Surrealistic Pillow

8)      Roland Kirk’s “various albums”

9)      Miles Davis’s 1959 Sketches of Spain

10)  Sandy Bull’s 1965 Inventions

With that list in mind, it should prove useful to explore a few names in depth – to look closely at the relationship between Hunter S. Thompson and the music he loved.

Bob Dylan

Dylan is a goddamn phenomenon, pure gold, and as mean as a snake.

That quote says it all, really. One could open nearly any Hunter S. Thompson book and find a glowing reference to Dylan. Dylan was there throughout much of Thompson’s life, singing about the changing times and documenting the turmoil of an unjust world. Thompson loved Dylan’s work, and viewed Dylan as one of his personal heroes. In interviews with Playboy and SPIN magazine he has even gone as far as to compare himself favourably with Dylan. He viewed both of them as artists against the world; leaders of the underground.

He told Harold Conrad that Dylan was one of the three most important men alive (alongside Muhammad Ali and Fidel Castro) and went on to say,

Bobby Dylan is the purest, most intelligent voice of our time. Nobody else has a body of work over twenty years as clear and intelligent. He always speaks for the time.

Let’s see. I just got the new Bob Dylan box set from the Rolling Thunder tour from 1975. It’s kind of a big package with a book and several CDs in there. It’s maybe the best rock and roll album I’ve ever heard.


In spite of the above list, one could argue pretty vigorously that Thompson’s favourite song of all time was “Mr. Tambourine Man.” Numerous sources testify to the fact that he would listen to this song before writing, and that it was a constant force throughout much of his life. He first heard it whilst living in San Francisco – surrounded by the musical forces of his day – and would play it over his custom-made 100 watt speakers from his home in the Rocky Mountains. When his most famous book, Fear and Loathing in Las Vegas, was published, Thompson dedicated it “to Bob Dylan, for Mister Tambourine Man.” Then, after his death – as decided decades earlier – it was the song that played as his ashes were fired from a giant Gonzo Fist at Owl Farm.

The story of an artist chasing his muse, it spoke to Thompson like no other song.

As a struggling journalist Thompson constantly wrote to his friends and family, and frequently advised them to listen to Dylan. He kept promising to send Paul Semonin – a friend in Africa – some Bob Dylan records, but of course, he kept running into financial issues. It is clear, however, that he felt Dylan’s work was important enough to spread around. When he first met the Hell’s Angels, in a story that is well known to Gonzo fans, Thompson brought the biker gang back to his apartment, while his wife and child cowered in another room. The group partied all night, with The Freewheelin’ Bob Dylan providing the soundtrack to this important meeting.

In 1968, Thompson wrote a long piece about hippy music in 1967, that appears at the very start of Fear and Loathing in America. In it, Thompson first describes Bob Dylan and “Mr. Tambourine Man.” He portrays Dylan as “the original hippy,” and his song as “both an epitaph and a swan-song for the… ‘hippy phenomenon.’”

Later in his career, Thompson found himself drawn to presidential candidate Jimmy Carter. This was largely due to Carter’s famous Law Day Address, from May 4 1974. For Thompson, justice meant the world. He was obsessed with right and wrong, and about the corruption and greed that he saw controlling his country. Carter’s speech meant a lot to him, and did so partly because Carter referred to Thompson’s favourite artist:

The other source of my understanding about what’s right and wrong in this society is from a friend of mine, a poet named Bob Dylan. After listening to his records about “The Ballad of Hattie Carol” and “Like a Rolling Stone” and “The Times, They Are a-Changing,” I’ve learned to appreciate the dynamism of change in a modern society.


Thompson recorded this speech and would play it back for friends, comparing it to General MacArthur’s “old soldiers never die” address.

This is perhaps a key to why Dylan meant so much to Thompson – a man whose work is characterised by an unrelenting attack on hypocrisy and injustice. Thompson saw in both Carter and Dylan an awareness of what was truly right. Dylan was a magnificent poet, but his work – like Thompson’s – sought to frame the guilty for their crimes, to expose the rank side of modern life and explore the possibility of change.

Jefferson Airplane


Although Jefferson Airplane only arrives at number six on Thompson’s list of his favourite albums of the sixties, a reading of his writing from and about that particular decade would suggest that he thought about the band, and in particular their singer, Grace Slick, a whole lot more than anyone except Bob Dylan.

His sixties-era writing is packed with references to his time in San Francisco, living in the Haight-Ashbury, and frequenting the Matrix. One night he witnessed the debut of a band called the Jefferson Airplane, and immediately began telling people about them. He seems to labour this point in his letters… He sent numerous notes to people to let them know that he “discovered” the Jefferson Airplane, and that he played some role in their rise to success.

He supposedly phoned Ralph Gleason and told him about the new band. Gleason became known for championing the Jefferson Airplane and helping them reach a greater audience.

The Matrix played a large part in Thompson’s life for a short period of time. Whilst writing Hell’s Angels, he used to ride through North Beach on his motorcycle, seemingly, just to watch Grace Slick in action. He said that she “made even the worst Matrix nights worth sitting through.”

After writing the book, whilst on his gruelling publicity tour, Surrealistic Pillow was released. Thompson demanded time out from his schedule, just to listen to the record. He could barely contain his excitement.

Upon hearing the first note I smiled. This was the triumph of the San Francisco people. We were all making it, riding a magical wave which we didn’t think would break.

His favourite Airplane song was, of course, “White Rabbit,” which he listened to for years after he left San Francisco. He claimed that its sound not only captured a vibe or a feeling, but a whole generation. It was the song of the sixties, in his eyes. When asked what he was trying to convey in his own work, Thompson once played Surrealistic Pillow for his publicist and said that was it. He said, “I could’ve written these lyrics myself. Today is my time.”

In his opus magnum, Fear and Loathing in Las Vegas, the Matrix appears in a brief flashback scene to what came before the fall of the sixties. It is viewed as an example of that wave that Thompson mentioned above, as well as in a more famous segment of his book. The song “White Rabbit” also appears in the novel. In one of the book’s more memorable moments, Dr. Gonzo demands that Raoul Duke (Thompson’s alter ego) play “White Rabbit” for him:

“Let it roll!” he screamed. “Just as high as the fucker can go! and when it comes to that fantastic bit where the rabbit bites its own head off, I want you to throw that fuckin radio into the tub with me.”


When Thompson left San Francisco and moved to Woody Creek, he found himself a home away from the madness. It was a place he could come to escape the world, and to give him some sense of security.

He needed his music, though. Away from the action, he had a custom-made 100watt amp that he used to blast inspiring music out over the mountains. These songs were fuel for his writing.

He once said,

I like to load up on mescaline and turn my amplifier up to 110 decibels for a taste of ‘White Rabbit’ while the sun comes up on the snow-peaks along the Continental Divide.


The Grateful Dead

Thompson’s love for the Grateful Dead is well known. He frequently makes reference to owning at least one Grateful Dead t-shirt, and the band’s name pops up throughout his body of work. Thompson even shared the same literary agent as the band.

As mentioned his list of favourite albums of the sixties, Thompson had a particular fondness for Workingman’s Dead. He said, in a letter found in his Fear and Loathing in America collection: “I think Workingman’s Dead is the heaviest thing since Highway 61 or ‘Mr. Tambourine Man.’”

His favourite song from this album – which it should be mentioned once again was released in 1970 and is thus not really a sixties album… – was “New Speedway Boogie.” This song was written in 1969 about the death of Meredith Hunter at Altamont, by a gang of Hell’s Angels who were hired as security. It was written by Dead lyricist Robert Hunter.

Thompson once said: “…at the moment my writing room is full of ‘New Speedway Boogie’ by the Grateful Dead. It says more than anything I’ve read in five years.”

Aside from the three “Hunter’s” involved, and the familiarity of the violence of the Hell’s Angels, Thompson was probably drawn to this song as an epitaph of sorts for the sixties. Thompson’s most famous work – and the most famous passage in that work – concerns the death of the idealism of the 1960s: “the high-water mark – that place where the wave finally broke and rolled back.”

After the advent of Gonzo Journalism, Thompson was taken by a burst of inspiration. He had – with Ralph Steadman – taken on the Kentucky Derby in his masterful short, “The Kentucky Derby is Decadent and Depraved.” He began tossing about the idea of taking Gonzo to all of America’s grand institutions. One such idea involved the America’s Cup. Thompson wrote numerous letters that announced his plan to commandeer a sort of Freak Press yacht and sail into the midst of the race with the Grateful Dead playing on deck.

Later, during George McGovern’s run for presidency in 1972 – which Thompson documented in his classic Fear and Loathing on the Campaign Trail ’72 – the author tried to bring the Grateful Dead on board the democratic nominee’s campaign. In the end, Warren Beatty successfully organised a fundraising concert that included the Dead, while Thompson merely suggested that McGovern go out in public while wearing “my Grateful Dead T-shirt.”

Come Join Uncle Sam’s Band

by James D. Irwin

It’s about ten past four on a Sunday afternoon. I feel like I’ve been beaten up; there is pain… bruises… cuts… none of them I can explain with any certainty. I think I have whiplash. I feel dead and decaying on the inside and all I’ve eaten is an apples, washed down with a few cups of coffee— the diet Christian Bale undertook for his role in The Machinist.

I could be doing this in better, more appropriate conditions. At least the sun is shining through the narrow window of my bare, white-walled room that’s covered in dirty laundry— all my clothes— and patches of mould slowly fading back from where it rained a few nights ago. And so I’m in a hovel of a room feeling like death could come at any moment, and would be quite welcome. But today is the deadline. So I better turn my thoughts to the subject I promised I’d write something on…

More build up first: a few months ago I got into a discussion with a few American friends about the notion of the ‘Great American Rock Band.’ We kind of concluded that there was no such thing. No band could compare to the cultural importance and impact of The Beatles or The Rolling Stones or Led Zeppelin. America has produced a great many rock bands, but none have the same cache… the same monolithic significance as the British bands that became big in the Sixties and peaked in the mid-Seventies. We talked about how Creedence Clearwater Revival were called ‘The American Beatles,’ but their success doesn’t translate. KISS has the success, but theirs is a success comparable to McDonald’s— the vast sales of products aren’t a signifier of quality.

But then perhaps comparing American groups to British groups doesn’t stand up. Maybe our cultures are just too different. It’s certainly true when it comes to literature. We have different standards… expectations. For example the ‘Great American Novel’ exists, and doesn’t need to compare itself to the British literary canon; it is instead focused more on the truest expression of America. This would draw The Ramones into the mix, but then they’d have to be thrown out. For as much as they embody a lot of the ‘American Spirit’ their music, whilst great, is tied forever to the narrow confines of punk culture, whether it should be or not.

I think perhaps the best we could do is compare the ‘Great American Novel’ to the ‘Great American Band.’ I have a friend who refuses to read American literature, something which I find incredibly narrow minded and downright stupid. There is a perception among some, like my friend, that because ours is the older country, with longer literary tradition ours is just better. And that’s what I was doing with bands earlier on. Maybe CCR are on par with The Beatles.

American literature is slightly different to British literature. Even now ours tends to be in the stuffy, uptight mould of Dickens and the Victorians. It’s modernised, of course, but our literary tradition remains very traditional. That goes for our journalism too. We never had ‘New Journalism’ or ‘Gonzo Journalism’… some of the best writing in the Twentieth Century… Meanwhile I’m getting marked down on my Non-Fictions assignments for not writing ‘properly.’ My tutor writes for The London Times.

I referenced Hunter S. Thompson in an accompanying essay, which didn’t go down well. British writers stuck in the notion of prestigious papers don’t like writers like Thompson. Only poetry professors have any time for Kerouac and the Beats; meanwhile guys like Norman Mailer and George Plimpton don’t get a mention. Neither does Tom Wolfe. So you transformed journalism in the 1960s? Well, not in Britain you didn’t. We like our journalism dry and fact based, keep your opinions to yourself…

Thompson’s Fear and Loathing on the Campaign Trail ’72 introduced me to the band that would eventually become my All Time Favourite Band: the Grateful Dead. They are also the band I think come closest to being ‘The Great American Band’, at least by my measure of comparing them to the ‘Great American Novel.’ Of course for this to stand up I should lay my cards on the table and state what I consider to be the ‘Great American Novel.’ We can safely assume it’s not Spider-Man #1, otherwise I’d still be talking about KISS.

There are strong arguments for a couple of books. It’s not The Catcher in the Rye though— miserable, whiny and a contributing factor to the murder of John Lennon. Huckleberry Finn is basically the sequel to a children’s book— a very good book, but not the greatest. Not the Muhammad Ali of American literature. The Great Gatsby lacks scope and scale… For me it’s not just a case of the Great American Novel, but the greatest novel I have ever read: The Grapes of Wrath by John Steinbeck.

Why? Because it has everything; it is epic in the scale of location, of human emotion… it has humour, sadness, is a timeless slice of history and, perhaps most importantly, has the Joad family chasing the same mythical American Dream Thompson failed to find in Fear and Loathing in Las Vegas.

It’s not my favourite Steinbeck novel either. That would be Cannery Row, in which Steinbeck revisited the Depression with a more romantic, nostalgic eye. One band wrote a song inspired by a rundown building that features in Cannery Row. Unless you’re mentally retarded, or just plain stupid, you can probably guess it was the Grateful Dead— the song being ‘Brokedown Palace’ from 1970’s American Beauty.

Both Steinbeck and the Dead are uniquely American. Britain doesn’t have any writers or bands than can really compare in terms of cultural relevance and significance. And wasn’t that what we were looking for earlier? Both the writer and the band have always been more popular in their own country than they have been in Britain. However, both have also been outsiders in their own time and place too.

The Grapes of Wrath was banned for a long time in a lot of schools and libraries on publication. Similarly the Dead were always an underground, counter-culture band that only the liberals dug and enjoyed. And it’s not like the Dead have always been cool. Through the mid-70s and most of the ‘80s they weren’t counter-culture, but simply obscure and faded. They had a resurgence though, and in 1987 finally scored a number one with ‘Touch of Grey.’

It took a long time, but both Grapes and the Dead finally got the recognition they deserved. Steinbeck’s novel is now widely regarded as one of the best ever, whilst the band from San Francisco finally got a bit of mainstream attention and recognition.

Maybe it’s a bit of a flimsy comparison… It’s not, I don’t think, meant as direct as a comparison as perhaps I’ve been attempting. I don’t know, but as far as I’m concerned the Grateful Dead are as close to a ‘Great American Band’ as there is.

They played at the President’s inaugural ball: Great American Band or not, they are Uncles Sam’s Band…

Hunter S. Thompson & The Lizards

Hunter S. Thompson and movie lizards.

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Flying Dog Beer

An interview with the makers of world’s most literary brews.

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Movie News: Hunter S. Thompson & Jack Kerouac Hit the Big Screen in 2010

News about Jack Kerouac and Hunter S. Thompson in the movies.

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Hunter S. Thompson & the Beats

Hunter S. Thompson was no Beatnik. For one thing, he was too late. By the time he was knocking out Gonzo journalism, Kerouac had died, the hippies had come to power, and Ginsberg had moved from Beat guru to counterculture superhero.

But Thompson frequently finds himself a place in the hearts of Beat readers, for he embodied a similar, although in some ways wildly different, ethos. Thompson was a rebel hero for a generation. His books shocked readers, appalled critics, and inspired millions. He didn’t seek to change the world in any grand way, but like the Beats, Thompson sought to point out its flaws, while working to create his own little place, a place where he could be free.

Thompson wasn’t a particularly great reader of Beat literature, either. He admired Kerouac’s discovery of Neal Cassady as a literary device, but disliked his style of writing. In Wenner & Seymour’s Gonzo: The Life of Hunter S. Thompson, Paul Semonin, a childhood friend of Thompson’s, claimed Thompson became interested in ‘beat culture’ in Puerto Rico, during the period Thompson later ficitonalised in The Rum Diary.

A letter to Jim Silberman (his editor at Random House) gives evidence of Thompson’s awareness of Beat literature, and some connection to it in his own work, as he talks about the Beats setting down a path that he could follow. It seems that he is suggesting that Kerouac and Ginsberg allowed him to write the way he did. In a 1965 letter to Carey McWilliams of The Nation, Thompson talks about his times around Columbia in ’58 to ’59, and says ‘I believe we were called “bums,” although “beatnik” quickly became popular.’ So at one stage Thompson did honestly consider himself a ‘beatnik’.

Yet, though one must look closely for these links, there are a few stories and connections that are less subtle. Thompson was a literary man, after all, and he had an opinion on his predecessors. He also got to meet many of them, albeit briefly, at various stages in his life.


The most obvious link Thompson had with the Beat generation was his connection to Allen Ginsberg. Although the two were hardly kindred spirits, they had a respect for one another, and came to half-befriend one another over many years. In a letter to William J. Kennedy, in 1968, Thompson described Ginsberg as “One of the few honest people I’ve ever met, for good or ill.”

In his The Book Report interview, Thompson said:

Yeah. Allen was a particular friend, one of my heroes, really. I knew him almost as long as I’ve been writing… I was once arrested with Ginsberg. He was a big help to me. He was one of the few people who read unknown writer’s work. Maybe he was just hustling me. He liked to flirt, Allen. They called him a monster but he was only falling in love.

In Douglas Brinkley’s The Art of Journalism: An Interview with Hunter S. Thompson, Thompson tells of his first encounter with Ginsberg. They met in San Fransisco, through a mutual weed dealer. Over several months, Ginsberg helped Thompson to edit a book he was working on at the time, Hell’s Angels.

Later, during Ken Kesey’s legendary party for the unification of the Merry Pranksters and the Hell’s Angels, Thompson met Ginsberg and Neal Cassady. This is the night of Thompson’s ‘arrest’ with Ginsberg, as the two drove to buy booze for the party, and were stopped by the police. Apparently, all Ginsberg could say to the police was, “I’m a poet… I’m a poet!”

In a 1965 letter to Murray Fisher at Playboy, Thompson explains that:

My tail-light lenses were cracked, so they cited me, and would have taken me and Allen Ginsberg to jail, I think, if I hadn’t been sporting a tape recorder. Ginsberg was so enraged by the harassment that he might want to write an ode about it. If it interests you, I’ll ask him. Anyway, neither my woody gard nor Ginsberg’s foot-long beard made the right sort of impression…

In a 1966 letter to Ginsberg, Thompson asks permission to use the whole of the poem, ‘To the Angels’ in Hell’s Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gangs. Thompson explains to Ginsberg how much he loves the poem, and how much it means to his book, and then promises that although he has no money, to give Ginsberg a percentage of the royalties of the book.

However, according to Michael Soheim, in Gonzo, Thompson and Ginsberg seemed to have fallen out sometime around 1970. He tells the story of when Thompson was drinking in the famous Jerome Bar in Aspen, and deliberately avoided meeting Ginsberg. Apparently Thompson owed Ginsberg “some time together.”

Corey Seymour tells a story that perhaps elaborates upon this. In 1994, at a Beat Generation Conference in New York, Thompson told Seymour several stories about Ginsberg, and finished by saying that he needed to get in touch, as they hadn’t seen one another in a long time. Hours later, Seymour met Ginsberg and told him how to contact Thompson. Thompson then briefly explained to Seymour that Ginsberg had been too embarrassed to speak to him since a “lost weekend” in the late sixties. “It’s a little-known fact, Corey, that Ginsberg was a horrible drunkard.” Thompson and Ginsberg met later that day.

Johnny Depp tells the story of Ginsberg’s memorial service in Los Angeles. Thompson was unable to attend, but agreed to write something if Depp would read it at the service. However, Thompson delayed and cancelled, until a minute before Depp was about to leave, expecting to go onstage with nothing to say, and Thompson faxed him a eulogy that described Ginsberg as “a dangerous bull-fruit with the brain of an open sore and the conscience of a virus… crazy, queer, and small…” and that he was looking forward to meeting the Grim Reaper “because he knew he could get into his pants.”


To Susan Haselden, Thompson wrote:

Certainly I’ve read The Subterranean: all his crap for that matter. The man is an ass, a mystic boob with intellectual myopia. The Dharma thing was not quite as bad as The Subterraneans and they’re both withered appendages to On the Road – which isn’t even a novel in the first place.

Doug Brinkley, the editor of Thompsons letters and his literary executor, knew better than anyone what Thompson thought of Jack Kerouac’s On the Road.

Hunter never really liked Jack Kerouac’s On the Road – he thought the writing was kind of sloppy and romantic and oversentimental – but he told me he thought Kerouac was a genius for two things: discovering Neal Cassady, whom Hunter thought was flat-out amazing, and using the literary construct of ‘looking for the lost dad I never had.’ Neal was never properly raised by a father. He didn’t even know whether his dad was alive or dead, and the notion of a young son who never had a dad, looking for his biological father, appealed to Hunter a great deal.

In Outlaw Journalist: The Life and Times of Hunter S. Thompson, William McKeen says that Thompson admired Kerouac’s On the Road, but only in the political sense. He disliked Kerouac’s other books, and wasn’t enthusiastic about the Beats as a movement. In a 1962 letter to Paul Semonin, Thompson wrote ‘I have tonight begun reading a shitty, shitty book by Kerouac called Big Sur.’ But there are many references to his having read, and been influenced to some small degree, by On the Road. Granted, millions of people Thompson’s age at the time were influenced by the book, but nonetheless it seems to creep up when people talk about the young Hunter S. Thompson. Thompson took a cross-country roadtrip that was allegedly inspired by Kerouac, and arrived in San Francisco to visit the areas made famous by the Beats. Semonin eluded to an influence Kerouac held over Thompson whilst in Puerto Rico, as the two young men read Beat literature and came to adopt Beat ‘personas.’

As much as anything, it seems Thompson was drawn to the same kind of thing as Kerouac. Thompson was intrigued by the bright lights and temptations of the city, but he was also drawn to wilderness. Both loved to get away from people. At different times, they ended up in Big Sur, a rugged wilderness that drew many Beat and counterculture artists to its magnificent crashing shoreline. When living in Big Sur and struggling badly for money, he submitted writing to Sterling Lord, Kerouac’s agent, and was rejected. This prompted one of Thompson’s many nasty letters in reply.

If we look at the authors’ two most famous works, we can see similarities. Both claim their works as both truth and fiction; both wrote travelling buddy stories; both detailed outrageous fun and drug use and youthful exuberance. In Thompson and Kerouac, the words just fly off the page at speed, as natural as thought. Their most famous novels were popular and critical successes, particularly long after the fact.

Kerouac and Thompson sought critical success as serious writers, but lamented the fact that their fame largely extended to frat boys and wild youngsters with a rebellious streak. Both died feeling that they lacked recognition for their work and that their lives had spiraled into decline with the burden of fame.

In 1995, Thompson was on the panel at the Jack Kerouac Conference in New York


We know that Thompson read William Burroughs and respected him, but not much else is clear. He certainly wished to be uttered in the same breath as Burroughs, and not because they both wrote explicitly about drugs or that they loved guns.

In 1997, after Burroughs’ death, Thompson wrote an obituary that was essentially the story of when the two writers met and fired guns together. At this time, Burroughs was an old and frail man, but he managed to make a huge impression upon Thompson by firing a powerful handgun with some accuracy. Twice during the article, he manages to make a joke about Burroughs killing Joan Vollmer.

William had a fine taste for handguns, and later in life he became very good with them. I remember shooting with him one afternoon at his range on the outskirts of Lawerence. He had five or six well oiled old revolvers laid out on a wooden table, covered with a white linen cloth, and he used whichever one he was in the mood for at the moment. The S&W .45 was his favorite. “This is my finisher” he said lovingly and then he went into a crouch and then put five out of six shots through the chest of a human-silhouette target about 25 yards away.

Later, in Hey Rube, Thompson refers to Burroughs as his friend, and says that the author was ‘robbed and badly beaten, many years ago, by a gang of paramilitary dope addicts who had never even heard of him’ in New York.

Neal Cassady

Early in his life, Thompson was apparently fascinated by Neal Cassady. According to Dou Brinkley, he thought the star of On the Road ‘was flat-out amazing.’

In 1966, Thompson decided he wanted to write a story about Cassady and Ken Kesey after the Merry Pranksters were arrested for marijuana possession. Thompson had become friends with Allen Ginsberg and was riding with the Hell’s Angels when the meeting between the Pranksters and the Angels occurred. There was a famous party that was written about by both Thompson and Tom Wolfe, and Neal Cassady was there. Sandy Thompson recalled that the party was wild, with everyone just ‘being high and silly.’

Gregory Corso

The connection between Corso and Thompson is neither obvious, nor easy to find. I only added it here because it stuck strangely in my mind and I spent a great deal of time, calling in many favours, to get the right reference.

In Paul Perry’s Fear and Loathing: The Strange and Terrible Saga of Hunter S. Thompson, there is a short story about when Thompson and Gene McGarr went to the Living Theatre on San Fransisco’s 14th Street to watch Kerouac read from Satori in Paris. Kerouac was naturally drunk and slurred through the performance. When Gregory Corso stepped on stage to read his poetry, Thompson and McGarr were enraged by his shortness and femininity, and proceeded to kick beer bottles, ending the performance and getting themselves thrown out.

Jack Kerouac & Hunter S. Thompson

by David S. Wills

Hunter never really liked Jack Kerouac’s On the Road — he thought the writing was kind of sloppy and romantic and oversentimental but he told me he thought Kerouac was a genius for two things: discovering Neal Cassady, whom Hunter thought was flat-out amazing, and using the literary construct of “looking for the lost dad I never had.” Neal was never properly raised by a father. He didn’t even know whether his dad was alive or dead, and the notion of a young son who never had a dad, looking for his biological father, appealed to Hunter a great deal. – Doug Brinkley in Jann Wenner’s Gonzo.

There are a great many similarities between the two legendary outlaw writers. For a start, both approached writing with firm literary influences, yet managed to create entirely unique styles of their own, almost unrecognisable from those authors they first wished to emulate. Hunter typed out whole novels by Hemingway and Fitzgerald, and ended up tearing pages from his notebooks and submitting them as professional journalism to internationally renowned publications. Jack was driven by the desire to be a proper novelist with proper respect and to be the darling of the literary world, yet wrote the novel that sent millions on the road, inspired drink and drug culture for decades to come, and died with the respect only of those whose respect he didn’t want.

They both wrote wild tales of excess and burned out American Dreams, celebrating that which the establishment would condemn as the dark side of life, and not giving a fuck. Well, not quite. Hunter often said he felt forced to live up to the image of himself that he’d created in his books, which blended reality and fiction so chaotically that it’s hard to tell what happened and what didn’t. Nonetheless, most of his fans tended to be young and reckless and seeing nothing more in their idol than a crazed dope fiend. Jack, too, was plagued by the brutal life wrought by celebrity. He had written most of his novels by the time he had published On the Road, and simply sat and slipped slowly towards death as he tried drunkenly to cope with the torment of unwanted attention. His books were largely condemned by the critics until after his death from alcoholism at the age of forty-seven.

In style, we can see sharp differences between them. Jack was of the Beat philosophy that avoided political solutions, and instead focussed on carving out one’s own little space in the world. Consequently, Jack celebrated in grand romantic sentiment the things in life he thought were worth living for. Hunter, on the other hand, was an angry and energetic force of nature, who tried to fight anything he didn’t like. If he saw a system of power, he’d destroy it. His writing was characterised by vitriol, taking whatever it was that he loathed and saying everything he could think of to persuade the reader of his point of view. In the end, both writers embraced a spirit and a feeling and stated it better than any of their contemporaries, but lacked any hard truth or adherence to a traditional literary style.

Hunter thought of his Fear and Loathing in Las Vegas as essentially a road novel, comparing it to On the Road. He felt that his book was like Kerouac’s in politics: In the pessimistic certainty of the death of the American Dream. Both books has protagonists against the prevailing ideology of their times, immersed in destructive lifestyles and ruing an oppressive world.