Freedomroo – The Great Art Behind Hunter S. Thompson’s Run for Sheriff

The Great Art Behind Hunter S. Thompson’s Run for Sheriff

If you’re going to curate an exhibition of vintage artwork related to the unorthodox and self-described gonzo journalist Hunter S. Thompson, prepare for the process itself to become a bit, well, gonzo.

Daniel Joseph Watkins learned this lesson the hard way. He had to figure out how to move “Freak Power,” an exhibition featuring the visually striking campaign posters designed for Thompson’s 1970 run for county sheriff in Colorado, from his Aspen-based gallery to Poster House in Manhattan, where it’s open through Aug. 15.

The posters, designed and silk-screened by the artist Thomas W. Benton, a close friend of Thompson’s and a fellow Californian turned Aspen activist, fused gut-punch electioneering (“Sell Aspen or Save It”) with visceral imagery (a clenched fist set against a sheriff’s badge). Surviving samples in pristine condition now sell for upward of $25,000. But that price tag pales in comparison to owners’ intense emotional attachment. “It would have been much easier to borrow a Warhol or a Rothko from some of these people,” laughed Watkins.

“Unfortunately, later in his life, Benton became consumed with a drug habit and had been trading and selling his artwork to several drug dealers,” he continued. One of those figures was willing to loan out several key Benton pieces. But he made it clear that if anything happened to them, filing an insurance claim would be the least of Watkins’s problems.

A suitably warned Watkins felt there was ultimately one person he could entrust to ship the posters east: himself. So last month he loaded up a U-Haul with the contents of the exhibition and personally drove it the 30 hours and nearly 2,000 miles to Poster House’s front doors.

“At night, I slept in the back of the truck with the artwork. I had a little bed there with a heated electric blanket. And I had a club,” he recalled matter-of-factly. “I had a friend following me in another car in case anything went wrong, and we would pull over to sleep in various Walmart parking lots.”

Poster House, the first museum in the United States devoted to the art of posters, opened in Chelsea in 2019, and the exhibition, co-curated with the artist Yuri Zupancic, is one of three on view in its gallery spaces. In addition to three dozen Benton posters, this show includes kinetic ink-splattered drawings by Ralph Steadman, whose illustrations accompanied many of Thompson’s articles; campaign trail photographs by the Aspen photojournalists David Hiser and Bob Krueger; and issues of The Aspen Wall Poster, a broadsheet newspaper designed by Benton and written by Thompson.

For Angelina Lippert, Poster House’s chief curator, the exhibition’s range of material offers a fascinating dichotomy. “Hunter S. Thompson is a chaotic figure,” she said. “We’ve all seen ‘Fear and Loathing in Las Vegas,’” the 1998 film with Johnny Depp portraying an unhinged Thompson. Steadman’s frenetic drawings echo that pinwheeling personality. Yet, “all of Benton’s posters are so reserved, quiet and direct in comparison,” Lippert went on. “It makes an incredible contrast to see these two guys expressing the same ideas in such powerfully different ways.”

To be fair, Thompson as a candidate couldn’t have been more different from Depp’s onscreen caricature. Instead, as seen in candid footage from Watkins’s own “Freak Power” documentary (2020), running daily as part of the Poster House show, Thompson was thoughtful and articulate — though his attitude toward politicking could be playfully wry. (Prepping for a public debate with the incumbent sheriff, Thompson secretly shaved his head so he could walk out onstage and — in the conservative parlance of the era — snidely refer to “my longhaired opponent.”) Most importantly, he was uninterested in mere symbolism, dismissing Norman Mailer’s 1969 New York City mayoral bid as “more a form of vengeance than electoral politics.” Thompson was running to win.

His “Freak Power” ticket signaled a pivot point for many Aspenites’ self-identity — catalyzing a movement to preserve the local environment with strict limits on real estate development; overhaul a police department, seen as wildly out of control; and legalize marijuana use. Once derided as merely “freak” concerns, they’ve since been embraced by local law enforcement or moved to the statute books.

“Anybody who thinks I’m kidding is a fool,” one of his local newspaper ads declared. “739 new registrations since the September primary is no joke in a county with a total vote of less than 3,000. So the time has come, it seems, to dispense with evil humor and come to grips with the strange possibility that the next sheriff of this county might very well be a foul-mouthed outlaw journalist with some very rude notions about lifestyles, law enforcement and political reality in America.”

In the end, Thompson fell short, as outlying areas of the county came out strongly against him, causing him to lose the election by nearly 7 percentage points. “We ran an honest campaign, and that was the problem,” he quipped to The Associated Press.

Nonetheless, Watkins insists you can lose a battle and still win the war: Thompson-aligned candidates, relying on his voter base and a fresh series of Benton posters, took majority control of the county commission in 1972 and the sheriff’s office in 1976. By 1986, the sheriff was a former Thompson campaign worker. Implementing Thompson’s ideas brought its own fallout, though.

“There were unintended consequences of some of the limiting of development, in that it limited the supply so much that demand went off the charts,” Watkins said of a resulting housing crunch. “It led to the transition of Aspen being more of a wealthy place. People come to Aspen now and ask, ‘Where did all the hippies go?’ There’s definitely some bitterness and disappointment about that.”

If nothing else, Watkins hopes “Freak Power” rescues Thompson’s legacy from the cartoonlike mythology that has built up around him. “When I bring up his name, sometimes people say, ‘You mean Hunter Thompson, the guy with the drugs and the guns and the craziness?’ No, I mean Hunter Thompson, the prescient political thinker who transformed a community with a radical campaign.”


Freak Power

Through Aug. 15, Poster House, 119 W. 23rd Street. 917-722-2439; posterhouse.org; timed tickets required.

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