True Stories

15 Particularly Insane Hunter S. Thompson Stories 

Coy Jandreau
Updated February 12, 2020 539.2k views 15 items

Hunter S. Thompson lived a pretty crazy life and there are plenty of true stories to prove it. This should come as no surprise, since just a few of his credos were: "Buy the ticket, take the ride," "I hate to advocate drugs, alcohol, violence, or insanity to anyone, but they've always worked for me," and "'Crazy' is a term of art; 'Insane' is a term of law. Remember that, and you will save yourself a lot of trouble." When these are the credos you live by, you find yourself in some crazy situations. 

Hunter S. Thompson was a man who played by his own rules to such an extent that he invented new ones, got other people to follow them, published his findings and called it all "Gonzo." His exploits are the stuff of legend. Who else could make a year-long stint on the campaign trail seem interesting to the masses? Or make going to the Kentucky Derby seem like the most insane trip of one's life? Who else could set the bar on the insane depravity that is Vegas? 

Hunter S. Thompson lived an amazing life, and he lived it his way right up until he was done with it. These are the craziest Hunter S. Thompson stories, may they inspire you to have some of your own. Buy the ticket. Take the ride.
That Time He Helped Free a Wrongly Convicted Woman
That Time He Helped Free... is listed (or ranked) 1 on the list 15 Particularly Insane Hunter S. Thompson Stories
Photo: Metaweb/GNU Free Documentation License

In 1998, Lisl Auman was convicted for shooting a policeman and sentenced to life in prison. An absolutely terrible crime, but there was absolutely no way she could have done it. None. Considering she was was handcuffed in the back of a police car at the time.

Auman was catching a ride with a friend of a friend when they were pulled over by the cops. She was then handcuffed and put in the back of the police vehicle. Meanwhile the driver pulled out a shotgun and shot the arresting officer, then 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 a thing wrong.  

She would've almost certainly spent the rest of her life in jail, if Thompson hadn't became involved. Auman wrote him personally and he became so upset by the case that he initiated a nationwide campaign to draw attention to the case. Calling on his celebrity friends (Benicio Del Toro, Johnny Depp, Jack Nicholson, and many more) and campaigning tirelessly on the issue.  

After seven years in jail, Auman was finally acquitted and released, thanks to Thompson. Unfortunately he never got to see it, having died earlier that year.

Auman remains a free woman, and the story has been optioned as a feature film. 

Sources: Listverse, The Guardian

That Time He Set A Yacht On Fire
That Time He Set A Yacht... is listed (or ranked) 2 on the list 15 Particularly Insane Hunter S. Thompson Stories
Photo: flickr/CC0

Before the full-fledged dive into the gonzo journalism that created Fear and Loathing in Las Vegas, Thompson covered the America’s Cup (a very prestigious boat race), and he brought illustrator/gonzo collaborator Ralph Steadman along with him.  

Steadman quickly noticed that Thompson was constantly downing pills, (that he claimed were for seasickness.) As this was well before the Fear and Loathing era, Steadman didn't know any better and took one of the pills himself. Of course they had nothing to do with seasickness - far from it. They were actually psilocybin, the hallucinogen found in mushrooms.  

It wasn't long until Steadman was seeing invisible red-eyed dogs and concocting plans to spray paint "F*** THE POPE" on the side of a yacht. Soon enough they were on a dinghy clinging to the side of a yacht trying to do just that. (They were caught by a security guard and made a frantic, haphazard, getaway.)

As the psilocybin began to wear off, the severity of what he'd almost done put Steadman into a blind panic. Thompson decided that firing off a flare gun would aid in their escape, and fired off two shots. The second of which landed on a nearby wooden yacht, instantly setting it aflame. The fire soon spread throughout the marina as people darted around in fear. A rescue boat eventually picked up the pair and they spent the rest of their trip listening to people tell them wild tales of the madmen who set the America's Cup on fire.

Source: Listverse

That Time He Stopped a Hell's Angel from Beating His Wife and Dog
Ranker Video
Video: YouTube

Hunter S. Thompson’s first book, Hell’s Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gang, took Hunter into the depths of an organization few men would dare infiltrate. In order to research the Novel he spent two years eating, drinking, riding, and living with the incredibly dangerous biker gang.

Things went well enough at first, he was accepted and allowed unprecedented access into their world without much trouble. He seemed able to not only separate his life from theirs, but also able to distance himself from the horrors and violence he saw them dole out on others.

That is until Thompson saw an Angel called “Junkie George” brutally beating his girlfriend. 

During the beating Junkie George's dog also tried to intervene and as he did George began beating the dog as well. This was too much for Thompson and he attempted to break up the fight telling George that "only a punk beats his wife and dog." The Angels wouldn't stand for that kind of disrespect and it earned Thompson such a brutal beating he wound up in the hospital.

This was the end of the unlikely truce between Thompson and the Hell's Angel's. Check out the above video for more of the story.

Source: Listverse
That Time He Ran for (and Almost Won) Sheriff of Aspen
That Time He Ran for (an... is listed (or ranked) 4 on the list 15 Particularly Insane Hunter S. Thompson Stories
Photo: flickr/CC0

Back in 1970 Hunter S. Thompson campaigned on the "Freak Power" ticket in Pitkin County, CO. Meaning, he was supported by members of the late-’60s counter-culture who felt they weren’t properly represented by the incumbent, Carol Whitmire.  

Thompson's platform was based around the promise to legalize drugs for recreational use (while dishing out corporal punishment on bad drug dealers). He also vowed to tear up the roads and carpet the streets with grass. He also planned to ban any building high enough to obscure the view of the landscape and rename Aspen “Fat City” in order to put an end to the “land rapers” who would develop the area further.

Naturally, Thompson quickly conflicted with the current Sheriff, who went as far as to threaten to arrest anyone who looked like they might vote for Thompson. There was also an incident where over 200 sticks of dynamite were stolen from a local ski company - they left behind a note threatening to blow up half of the county if Thompson was elected. Thompson’s reply was... well it was very Hunter S. Thompson: he shaved his head so that he could refer to his conservative, crew-cut rival as “my long haired opponent.” 

Eventually, (and shockingly) it began to look like Thompson might actually win. To make sure that wouldn't happen, Whitmire, a Republican, made a rare deal with the Democratic candidate to consolidate their votes. Thompson lost by a mere four votes.

Source: Listverse