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10 Bizarre Exploits Of Hunter S. Thompson

by Aaron Short
fact checked by Jamie Frater

A list of the bizarre activities undertaken by legendary writer Hunter S. Thompson could probably stretch into the hundreds of thousands. So for this article we’ve selected ones that stand out as strange even by his standards. And since we’re talking about the man who wrote Fear and Loathing in Las Vegas and invented gonzo journalism, they are very, very weird indeed. So, enjoy, but remember—buy the ticket, you take the ride.

10He Shot Up His Neighbor’s House


Photo credit: MDCarchives

In 1985, a multi-millionaire called Floyd Watkins moved to Woody Creek, in Aspen, Colorado. He bought Beaver Run Ranch, just a few miles from Owl Creek—which just happened to be the ranch of one Hunter S. Thompson. It wasn’t long before the two men were at each other’s throats. Watkins, who’d made millions running a debt-collecting firm, immediately began surrounding his property with concrete walls and chain link fences, pouring tonnes of concrete, redirecting streams to create artificial trout farms (to the annoyance of his neighbors downstream), and demanding that the county’s dirt roads be paved with concrete just so that dust wouldn’t find its way into his home. When his requests for the roads to be paved were denied, he boasted that he was rich and powerful enough to have every member of the county board fired and replaced if they didn’t do what he said. As if to prove just how powerful he was, Watkins even imported Bengal tigers to deter trespassers.

Watkins’ supervillain-esque levels of control freakery didn’t endear him to the residents of Woody Creek. He was almost immediately bombarded with threatening phone-calls, vandalism, and unflattering graffiti (ranging from foul language to a sign declaring his house “Fat Loyd’s Trout Farm”). How much of this was the work of Thompson we’ll never know, but Watkins did blame Hunter for at least one of the incidents—the mysterious poisoning of his expensive trout.

Things came to a head when Watkins chased down a resident of Woody Creek, warning them that he intended to hire professional gunmen to patrol his property and that if anyone messed with him he could get rid of them without ever being implicated. Thompson must have heard about this and taken exception, because that night, as a heavily armed Watkins camped out in his car, his gaudy mansion was lit up by gunfire. Someone fired scores of bullets from a shotgun, automatic rifle, and finally a pistol in the direction of Beaver Run Ranch, pausing only to reload or switch weapons.

According to Wilson, he chased the perpetrator in his car at high speed and when they pulled over it was Thompson, completely unapologetic about the shooting—it had been a warning against further ecologically destructive development. Later, Thompson’s excuse for the shooting was that he had been attacked by a rabid porcupine and had fired at it (with pistol, shotgun, and automatic rifle) in self-defense. When Thompson was ordered to present his automatic rifle to the police it had been destroyed in such a way as to make ballistic tests useless. No charges were brought.

9He Went Looking For Pygmies Instead Of Watching The Ali Fight


In 1974, Thompson and his illustrator, Ralph Steadman, were dispatched to Zaire to cover the Rumble in the Jungle between Muhammad Ali and George Foreman. It was one of the weirdest events in sporting history—hosted by an eccentric African dictator, covered by the world’s top journalists, and pretty much impossible to get tickets for. Of course, Hunter and Steadman had their tickets provided by Rolling Stone—as well as their travel, expenses, and accommodation. But instead of attending the fight, Hunter gave away his tickets (or, according to Steadman, sold them for weed) and set off into the jungle to search for the wanted Nazi war criminal Martin Bormann and to find pygmies, in order to ask if it was possible for them to eaten by cobras. Whether he met pygmies is unclear, but he did meet some locals who he bought ivory from. He also told them he was George Foreman’s doctor…Dr. Bormann.

After the fight was over, the famous writers George Plimpton and Norman Mailer arrived back at their hotel to find Thompson floating naked in the hotel pool, high as a kite and drunk on Wild Turkey. He didn’t even know who’d won. And this wasn’t even the end of the debacle. When Thompson and Steadman arrived back in the US, Hunter’s ivory was confiscated by customs. Rather than simply paying the fees (he had no idea they were only around $60) Hunter charged past airport security, jumped over a desk, grabbed the tusks and ran for it, with airport security hot on his heels.

8He Set The America’s Cup On Fire


Another of the bizarre situations Thompson involved Ralph Steadman in involved a regatta, a million dollar yacht, some anti-papal graffiti, a flare gun, and a terrible fire. In a precursor to the same sort of gonzo journalism that created Fear and Loathing in Las Vegas, Thompson decided to cover the America’s Cup (a prestigious boat race), dragging Steadman along to illustrate the adventure. After hiring a sloop so they could get in on the action and better cover the race, Steadman noticed that Thompson was guzzling pills—which he claimed were for seasickness. Inexplicably not knowing any better, Steadman took one of the pills himself, before realizing they were actually hallucinogenic psilocybin. Pretty soon Steadman, who was now seeing invisible red-eyed dogs, suggested that it would be funny to spray-paint “F*** THE POPE” on the side of one of the yachts.

Pretty soon the two of them were on a dinghy, trying their best to spray graffiti onto an expensive yacht. When a security guard turned up and asked them what the heck they were doing, Thompson panicked and the two made a clumsy getaway, retreating to the sloop. At this point Steadman was starting to freak out as the psilocybin wore off and he realized what he’d almost done. Things soon got worse as Hunter produced a flare gun and fired two shots—the second of which hit a wooden yacht,
setting it on fire. The whole docks burst into panic as people rushed about battling the spreading flames and searching for the people who’d set off the flares. Hunter and Steadman ended up being rescued by a fishing boat and spent the morning in a cafe listening to people rave about the maniacs setting boats on fire.

7He Almost Drowned Bill Murray


In the early ’80s, Thompson was spending a lot of time with Bill Murray, who had met Hunter after agreeing to play him in Where The Buffalo Roam. One night, when Murray and Thompson were getting drunk and challenging each other to a game of Houdini-esque escapes (because how else would that combination of people entertain themselves?), Murray was fairly confident that he’d be able pull of a daring, underwater rope escape. So Thompson tied him to a chair and kicked him into a swimming pool. It soon became apparent that Murray couldn’t escape, and was, in fact, drowning—which may have had something to do with the fact they’d used duct tape instead of rope. Luckily, Thompson was able to rescue Murray from the swimming pool just before he drowned.

This wouldn’t be the last time Thompson almost killed the person playing him in a movie, either. Twenty years later, Johnny Depp also spent a lot of time with Hunter in order to get into character for Fear and Loathing in Las Vegas. While he was staying at Owl Creek, Thompson made up a room for him the the basement. Depp was about to light one of his trademark cigarettes when he realized that the box that his ashtray was sitting on was actually a box of dynamite. Quickly stubbing out his cigarette, he realized the entire basement was full of dynamite. Hunter later explained that the dynamite was for making bombs. He further clarified that statement, saying: “If you’re making cake, you’re gonna need some flour.”

6His Bizarre Interview With Keith Richards

Hunter S Thompson interviews Keith Richards from the Rolling Stones

What happens when an unstoppable force meets an immovable object? Well, if the unstoppable force is Keith Richards and the immovable object is Hunter S. Thompson, we may have an answer to that. In 1993, ABC’s “In Concert” series was promised an interview with Richards at his most insane, drug-fueled stage of rock star excess. Unfortunately when it came time to conduct the interview, Richards decided that he wanted more money, locking his door and refusing to open it. Desperately searching for a solution, ABC decided to fight crazy with crazy, by asking Thompson to conduct the interview. Hunter agreed, but there was still the issue of the locked door, which he solved by hooking up a recording of a pig being slaughtered to a megaphone and blasted it at the locked door until a bewildered—and armed—Richards opened up. You can see the full interview above—pay attention to Thompson’s first line “Hi. My name is Hunter S. Thompson and I haven’t been paid yet.”

5His Birthday Gift To Jack Nicholson: Elk Hearts, Blinding Light, And Gunfire


Another of Thompson’s celebrity friends was Jack Nicholson. For some reason, the pair had got into the habit of giving each other weird gifts. So on Nicholson’s birthday, Thompson decided to give him a…unique birthday greeting. Arriving at Nicholson’s house after dark, Thompson announced his arrival by climbing up onto a ridge overlooking the building and setting off a 40-million-candlepower parachute flare—this lit up 40 miles of darkness and produced an effect something like “the first flash of a nuclear explosion.” Then, in quick succession, he aimed a million-watt spotlight at the house, played the amplified sounds of his ever-popular dying pigs tape through a loudspeaker, and began firing his automatic pistol into the air.

Jack Nicholson did not come outside.

What Hunter didn’t know was that Nicholson’s nerves were already frayed, since he was being stalked by a deranged fan at the time. When Thompson got no reaction from the gunfire, blinding light, explosions in the sky, and terrifying noises, he deposited a fresh elk heart on Nicholson’s doorstep and left feeling as if he’d been snubbed.

4He Made Friends With Richard Nixon


If Hunter S. Thompson had a nemesis it would surely be his old enemy Richard Nixon. Thompson had tried every tactic available to smear, enrage, or destroy Nixon in his early career. He even once threatened to leave the US forever if Nixon was re-elected (he was and Thompson didn’t). It was clear that he had a blinding hatred for the man. However, while writing Fear And Loathing on the Campaign Trail something very bizarre happened. Somehow Hunter managed to wrangle an interview with Nixon himself. He didn’t have long, just a short car ride to the airport with the President, but it had the potential to go down in history, like the Frost/Nixon interview eventually did.

What would happen? Would Thompson cement his position as one of the greatest political writers of the 20th century by deconstructing the man he blamed for the dire state of his country? Well, no. Instead he found himself having a polite conversation about football with his old enemy. Whether Nixon even knew who Thompson was is unclear, but Hunter described the weird chat as like talking to an old buddy.

Still, this is Thompson we’re talking about, so there was one event that freaked out Nixon’s security. When the car stopped at a gas station to refuel, Thompson got out, lit up a cigarette, and almost blew them all to smithereens. Despite the apparent bonding that went on during that weird car ride, Thompson still described Nixon as having an “ugly, Nazi spirit” in his obituary.

3Getting Beaten Up By Hell’s Angels

Hunter S. Thompson meets a Hell’s Angel, 1967 | CBC

In 1966, Thompson’s first book was published: Hell’s Angels: The Strange And Terrible Saga Of The Outlaw Motorcycle Gang. To research the piece, Thompson spent two years living with, observing, writing about, and being terrified by actual Hell’s Angels. At first the arrangement was amicable, Thompson was accepted by the Angels and gave the world an unprecedented glimpse into their way of life, while seeming almost immune to the terrifying violence he witnessed the Angels dishing out to others. Then one day Thompson saw an Angel called “Junkie George” administering a particularly brutal beating to his girlfriend.

During the assault, George’s dog ran in and began biting him, causing the biker to start beating the dog as well. Thompson, disgusted, tried to intervene, telling George that “only a punk beats his wife and dog.” This earned him a tremendous beating from Junkie George and the rest of the Angels in attendance. They threw him to the floor and reigned down kicks and punches, with one trying to smash a rock over his head—luckily it missed. Thompson was left hospitalized, and the incident brought his association with the Angels to an ugly, definitive end. The event left a mark on Thompson, evident in the above clip, where Hunter is surprised by the appearance of one of the Angels who’d given him the beating on a 1967 chat show.

2He Helped Free A Wrongly Convicted Woman


Photo credit: Steve Anderson

In 1998, Lisl Auman was sentenced to life in prison for shooting a policeman—despite the fact that there was no way she could have committed the crime, since she was handcuffed in the back of a police car at the time. The official version of events went like this: Auman was catching a ride with a friend of a friend when they were pulled over by the cops and she was handcuffed and put in the back of the police vehicle. While this was happening, the driver pulled out a shotgun and shot the arresting officer, followed by himself. Under the felony murder law, Auman was held accountable for the crime and sentenced to life without parole, even though she hadn’t personally done anything.

It looked like she would spend the rest of her life in jail—until Thompson became involved. After receiving a letter from Auman, he became so incensed that he kickstarted a nationwide campaign to draw attention to the case. He used his connections to get celebrities involved (Benicio Del Toro, Johnny Depp, Jack Nicholson, and many more) and campaigned tirelessly on the issue. Eventually, after seven years in jail, Auman was acquitted and released. Unfortunately Hunter didn’t live to see it, having died earlier that year. Auman remains a free woman, and her story will soon be adapted into a Hollywood movie.

1He Ran For Sheriff

Hunter S. Thompson for Sheriff Campaign

In 1970, Thompson launched one of the most bizarre campaigns in political history, when he stood for Sheriff of Pitkin County, Colorado. Thompson had the support of the “Freak Power” ticket—meaning he was supported by members of the late ’60s counter-culture who felt they weren’t adequately represented by the incumbent, Carol Whitmire. If Thompson was elected he promised to legalize drugs for recreational use (but use corporal punishment on bad drug dealers); he would also tear up the roads and carpet the streets with grass (actual grass, not marijuana). Further to this, he would ban any building high enough to obscure the view of the landscape and rename Aspen “Fat City” to deter “land rapers” who would develop the area to the detriment of the local ecology..

Thompson immediately butted heads with the sitting sheriff, who employed dirty tricks like threatening to arrest anyone who looked like they might vote for Thompson. There was also an ugly incident where over 200 sticks of dynamite were stolen from a local ski company. The thieves left behind a sinister note threatening to blow up half of the county if Thompson was elected. Thompson’s reply was to shave his head so that he could refer to his conservative, crew-cut rival as “my long haired opponent” during debates. Eventually, to Thompson’s horror (he had never expected things to get this serious), it began to look like he might actually win. To make sure that didn’t happen, Whitmire, a Republican, banded together with the Democratic candidate to consolidate their votes. Hunter ended up losing by just four percentage points. Still, fif not for a few votes, Aspen might be called Fat City today.

Aaron is some kind of high powered mutant never even considered for mass production. Half Welsh, half Jamaican and all insane. Hurry up and join him on Twitter.

fact checked by Jamie Frater