Fear and loathing in Aspen: Inside Hunter S. Thompson’s unlikely run for sheriff
Trailblazing ‘gonzo’ journalist Hunter S. Thompson ran for sheriff of Aspen in 1970. A Kennedy is telling that tale. Sheila Flynn writes
The latest headlines from our reporters across the US sent straight to your inbox each weekday
Your briefing on the latest headlines from across the US
Almost everything even tangentially related to Hunter S Thompson features elements of the absurd, unexpected or downright wild.
So it’s only fitting that a new feature film about the late writer’s out-of-left-field, whirlwind run for sheriff of Pitkin County, Colorado in 1970 came about through the efforts of a cast of characters so diverse that it would’ve made the Fear and Loathing in Las Vegas author proud.
The director is a scion of the Kennedy clan.
A former CIA officer – who also happens to be that Kennedy’s wife – is one of the stars and a producer.
So is his stepmother, actress Cheryl Hines, whose husband (Robert Kennedy, Jr) is one of the most infamous proponents of the anti-covid vaccine movement.
Oh – and then there are the hurdles of film financing, title changes, logistics ... and Covid.
No big deal.
Bobby Kennedy III’s feature directorial debut, then titled Freak Power, was slated to premiere at the South by Southwest festival in Austin in March 2020. But the event – a traditional staging area for innovation in tech, film and music – was cancelled days beforehand in a signal of the widespread covid lockdowns to come.
Since then, Mr Kennedy, 37, and the team behind the film have changed the name of the production and secured distribution rights; now titled Fear and Loathing in Aspen, it can be viewed on demand and streaming on various platforms.
Even the origin story for the new Thompson film lives up to the writer’s reputation.
“I was living as a ski bum in Aspen,” Mr Kennedy tells The Independent. “I was living out of a bus ... and I guess, because I was new, I was getting a lot of the old stories out of the old lads who I’d run into – and then I kind of noticed this ‘Hunter Thompson for Sheriff’ poster in my favourite bar and was like, ‘Huh – I wonder what that’s about.’”
The fledgling filmmaker then went to the local historical society and browed old newspapers to research the tale behind the gonzo journalist’s political foray.
He decided, “Well, this is a highly pertinent story for right now, because it’s just like somebody trying to run a wedge between the two political parties who have both sort of gone stagnant,” he tells The Independent. “I think that’s definitely a message for today in America.”
Mr Kennedy, 37, is the son of Robert Kennedy, JFK’s younger brother who was assassinated five years after the president while following in his political footsteps.
Robert Kennedy, Jr, the 67-year-old late senator’s son, is the director’s father. RFK Jr has been widely blamed for disseminating anti-vaxx information online, and he is married to actress Cheryl Hines, famed for her role opposite Larry David in Curb Your Enthusiasm.
The director has been married to Amaryllis Fox, a former CIA officer whose life is currently being turned into a show, since 2018. The pair have a toddler and a baby who is less than two months old.
A lot was happening in Mr Kennedy’s personal and professional life as the film gathered steam, but he was committed to bringing an oft-forgotten story to life.
“I’ve loved him since I first read him in college,” says the director, who currently lives in California. “And it’s something that I’d never heard about - and it was possibly the most significant event of [Thompson’s] life. I mean, that just screams a good story.”
He believes that, “certainly, the average public, and I would say even the average Hunter Thompson fan,” doesn’t know about the gonzo writer’s law-enforcement bid.
“For the most part, this was a little lost episode of history,” Mr Kennedy tells The Independent. “It was nice to get to bring it back.”
It’s a cult story that has been circulating for decades among hardcore Hunter S. Thompson fans - but the new telling will bring the strange saga to a wider online streaming audience.
Mr Thompson bought a property in Colorado in 1967 and subscribed to far-left ideologies that would legalise drugs, prioritise nature and generally disrupt the status quo during the already-tumultuous America of the 1960s. Just a few years later, he would attempt further disruption with his run for sheriff and a platform rooted in those beliefs.
He wrote a seven-age article for Rolling Stone about the 1969 mayoral race of “Freak Power” candidate Joe Edwards titled The Battle of Aspen - teased as Freak Power in the Rockies - and soon decided to run himself on on “a six-point platform that included changing the name of Aspen to ‘Fat City,’ installing a ‘bastinado platform’ and set of stocks on the courthouse lawn in order to discourage ‘dishonest dope dealers,’ and disarming the sheriff and his deputies,” according to the Aspen Daily News.
It would be great to “challenge the establishment with a candidate they’ve never heard of,” Mr Thompson wrote in Rolling Stone. “Who has never been primed or prepped or greased for public office? And whose lifestyle is already so weird that the idea of ‘conversion’ would never occur to him? In other words, why not run an honest freak and turn him loose, on their turf, to show up all the normal candidates for the worthless losers they are and always have been?”
Thompson was running against local sheriff Carroll Whitmire, a traditional old-school Western official, and the writer’s assembled team for the campaign was as haphazard as anyone could expect. He lost, unsurprisingly - but perhaps more shockingly by only a few hundred votes.
The Kennedy project finished more than half a lifetime later was equally ramshackle, the director tells The Independent, laughing about the “trials and tribulations of independent film.”
Major studios had wanted the project, he says, but with much better-known names attached who didn’t necessarily fit the parts in his mind. Instead, he and his team opted to maintain creative control and most of the funding came from independent donors.
“Luckily, Hunter’s got a lot of fans,” Mr Kennedy says, of the author, who took his own life in 2005 at the age of 67 on the same land in Colorado. Johnny Depp- who famously portrayed the writer in the film adaptaton of Fear and Loathing in Las Vegas, financed the majority of his funeral arrangements - which included his ashes being shot from a cannon.
The similarly fantastic story of Mr Thompson’s sheriff race has been told in various guises previously, but Mr Kennedy says he believes “it was good timing” for this new feature as America’s polarisation intensified.
But in fitting Thompson form, more drama ensued after filming began in Colorado.
“One day the Hell’s Angels came down on us and tried to take away our costumes,” Mr Kennedy laughs. “Another time, one of our set designers ran a truck into the .... [set] and knocked the power out there for about three weeks, which completely screwed us.
“There were just various, crazy episodes as a result of pulling in a lot of favours - and getting people to work for free,” Mr Kennedy says of the filming, which took place in Silverton, Colorado. “All of our extras were just people who showed up to party, and a lot of them showed up with their own party supplies. So they weren’t the most reliable group, most of the time ... it was a gonzo-style affair.”
He continues: “In a funny way, the actual kind of story of what happened [was] just like Hunter. He kind of moved into this small town and tried to take it over. Our production kind of moved into this small town and increasingly increased its population size ... I think like a third of the town loved us, a third of the town were skeptical, and a third of the town wanted us to get the f**k out.”
He says: “You could certainly write a movie about the making of this movie.”
Unlike many of his family members, Mr Kennedy seems determined to remain in entertainment and has not yet ventured into politics - though he’s not exactly shy about sharing views.
“Hunter made some extremely strong arguments for the need for a third party in America ... I think he also made some extremely strong arguments for police reform,” Mr Kennedy says. “Those two themes are kind of where I think that his sort of wisdom is just relevant today.
He adds: “I think a third party, at least here in America, definitely seems to me to be the only way forward at this point. Just these two Republican and Democrats banging their heads together and not talking .... it doesn’t seem to be solving much.”
He says he hopes people take away inspiration from political debate and a bonafide renegade in Thompson - but in the meantime, he and his wife are working on future film and TV projects, whether about their lives, social justice or other topics.
“It’s nice to have some irons in the fire,” he says. “It’s a fun job.”
Subscribe to Independent Premium to bookmark this article
Want to bookmark your favourite articles and stories to read or reference later? Start your Independent Premium subscription today.
Join our commenting forum
Join thought-provoking conversations, follow other Independent readers and see their replies