Trailblazer, nonconformist, rebel and rogue, the man who created Gonzo journalism and whose writing helped define a generation was determined to live by his own rules. It was a decision that took its toll – on himself and others. Ian Harrison goes in search of one of his heroes…
James Squire

17 Jul 2014 - 2:44 PM  UPDATED 24 Jul 2014 - 2:50 PM

I must create a system or be enslaved by another man’s. – William Blake, “Jerusalem”

Every hero becomes a bore at last. – Ralph Waldo Emerson

I think of a hero as someone who understands the degree of responsibility that comes with his freedom. – Bob Dylan

It was probably the 1977 Carter press conference. That was the fork in the road.

Members of the White House press corps aren’t supposed to outdraw the President. But there was Hunter Stockton Thompson, Rolling Stone correspondent, surrounded by ostensibly, the finest representatives of the Fifth Estate and being hounded for autographs while Jimmy Carter, Leader of the Free World, looked on in bemusement.

By this time, Thompson was a fixture – albeit a sporadic one – in the pages of Rolling Stone, and a thorn in publisher Jann Wenner’s side. It was a turbulent relationship that grew more strained as Thompson lost his anonymity and became part of every story he wrote for the magazine, whether about election year politics or Vietnam.

It’s a testament to Wenner’s patience and Thompson’s considerable charm and talent as a writer that he didn’t burn that bridge entirely when he failed to file a word on the Rumble in the Jungle in 1974. While his Louisville pal, Muhammad Ali – of whom Thompson once wrote: Muhammad Ali, one of my very few heroes, once took the time to explain to me that ‘there are no jokes. The truth is the funniest joke of all.’ – tussled with George Foreman in the ring, Thompson floated in his Kinshasa hotel pool in a drunken stupor. That trip to Zaire was a write-off for Rolling Stone.

There were others. Missed deadlines, broken promises, opportunities lost. But Rolling Stone was the least of it. If Jann Wenner suffered Thompson’s mood swings and vices, only the writer’s first wife, Sandra Dawn Conklin, knew just how diabolical and incurable they were.

Heroes don’t always age well, but Hunter S. Thompson was more than just a stock cautionary tale of to hell in a handbasket excess. He, like Blake’s character, raged against the system and desperately sought to impose his own order. But he did so at his own peril and, tragically, used his Me v. The Establishment crusade as a crutch to excuse some terrible, abusive behaviour – all of it self-inflicted and, often, directed at his own family.

That Thompson was a genius is not in dispute. Fear and Loathing in Las Vegas and Fear and Loathing on the Campaign Trail will forever live on as seminal counterculture romans à clef. His essays – the early ones especially – evince the brilliance and prescience of critical thought that led Tom Wolfe to call him one of the best American writers of the 20th century.

But Thompson implicated himself so thoroughly into his reportages – embedded himself, well before the term was de rigueur – that his legacy faces a different kind of retrospective scrutiny than, say, that of a conventional journalist or writer.

Thompson was a shameless self-promoter who, in defiance of Dylan, never did come to terms with the responsibility that came with his freedom. He wrote prolifically and well for a short burst of time – a crucial time in American history -– and was the messianic distillation, for many, of a movement’s barbed indignation. But the perils of hero worship bit back for Thompson’s most ardent acolytes and, indeed, for the man himself (that same hero worship was, in a sense, a symptom of the man’s narcissism).

And he could be a monster. He was a philanderer with an explosive temper and a collection of guns who scared the shit out of his wife and son (Conklin uses the words ‘vicious’ and ‘cruel’ to describe her husband in the 2008 documentary Gonzo: The Life and Work of Dr. Hunter S. Thompson). His love of firearms, booze and drugs is part of his mystique and legend, of course, but try to live with that for the better part of fifteen years, as his family did.

When Thompson became a caricature of his former self – appearing incoherent on Late Night with David Letterman in the 1980s and, in 1997, same time slot, same network, drunk and machine gun happy with Conan O’Brien – and consorted more intimately with his inner torments, it was like a personal manifestation of his poetic remark about the watershed 1968 Democratic National Convention, writ large: ‘The wave broke, and rolled back.’

Hunter S. Thompson was self-aware. For a man constantly daring fate to tempt him with an excuse to blow his brains out, the gradual ebb into inevitable oblivion must have had a sobering effect. When Garry Trudeau started satirising Thompson in Doonesbury via the character Uncle Duke – a patent lampoon, in name and appearance, of the writer’s Raoul Duke persona from Fear and Loathing in Las Vegas – Thompson commented that ‘some people grow up and want to be firemen, and some want to be president; nobody wants to grow up and be a cartoon character’.

He knew. This ‘proud freak’ knew he was impotent, knew he was a slave to the bottle, to the seductive lure of money and fame. As a boy, The Great Gatsby had taught him that the fix was in. F. Scott Fitzgerald was a scornful voyeur of the rich but his unlikely literary apprentice was more wont to smash the windows in and burn down the gates. But revolutionary desires are difficult to pull off with a pen and a sober mind, let alone one under the spell of alcohol and drugs.

Radical zeal rarely takes root in inexhaustible supply and is all the more difficult to sustain in those who wrestle with so many personal demons and, who, to crib the words of novelist Hari Kunzru, often make themselves ugly to expose the ugliness around them.