Freak Power: Aspen is getting weird again

By Jay Gentile, CNN

Aspen, Colorado (CNN) — Come for the five-star hotels, high-end boutiques and world-class skiing that have helped make Aspen one of the world’s most desirable luxury destinations.

Stay for the artists, eccentrics, ski bums and freaks hiding in plain sight.

It’s been more than half a century since famed American author and former Aspen-area resident Hunter S. Thompson’s Freak Power movement helped define this Colorado ski town as an unlikely countercultural outpost for intellectuals, artists and unconventional thinkers.

This onetime silver mining hub first began attracting creative types in the 1940s, when influential art enthusiasts Walter and Elizabeth Paepcke pioneered the Aspen Institute and were involved in the founding of the Aspen Skiing Company.

Yet despite Aspen’s modern-day reputation for glitz and glamour, the Thompson-esque freaks are still here.

And DJ Watkins is one of them.

“Freaks are people that don’t want to live in the traditional, cookie-cutter lifestyle of suburban America,” says Watkins, a local author, curator and gallerist who has made something of a life’s mission of keeping Aspen’s countercultural flame alive. “And Aspen has always attracted people like that.”

From his Aspen Collective gallery behind the historic 19th-century Wheeler Opera House, Watkins showcases work tied to Aspen’s countercultural past alongside contemporary artists from across Western Colorado’s Roaring Fork Valley. He also runs Fat City Gallery — named for Thompson’s proposed moniker for Aspen when he ran for sheriff in 1970 — and has worked to connect Aspen’s galleries through the Aspen Art Walk.

Watkins readily acknowledges the “conspicuous consumption” and “materialism” associated with modern Aspen. But he says that’s not the full story.

“There’s a resurgence of local culture happening right now,” he says.

Watkins also points to a constellation of venues carrying Aspen’s creative tradition forward today. Buckhorn Public Arts has transformed a former commercial space into artist studios alongside Eddy’s, a locals-friendly restaurant and market. The city-run Red Brick Center for the Arts offers community classes and studio space, while the Paul JAS Center and Wheeler Opera House bring world-class performances to town at affordable pricing. Watkins also notes community events like the Aspen Design Conference as evidence of a new generation putting its own stamp on Aspen.

A town built for characters

Despite its modern-day reputation as a “billionaires’ playground,” Aspen has a long history of not taking itself too seriously.

Consider, for example, the fine art of “mall bowling.”

When the bricks of Aspen’s downtown pedestrian mall were being laid in the 1970s, members of the entirely fictitious Aspen State Teachers College (founded on a joke about how Aspen resembled a college campus) decided the unfinished stretch looked an awful lot like a bowling alley, according to Aspen Historical Society archivist Anna Lookabill.

So naturally, they went bowling… with a beer keg as the ball and the “students” as human bowling pins, even staging a 7-10 split for the camera.

The same irreverence made its way onto the mountains, where loosely organized ski gangs developed their own names and rituals. One group, the Dogs, was known for barking at people in the lift line. And the tradition isn’t merely historical: A younger Aspen ski gang today has adopted perhaps the most fitting name of all — the Freaks.

Yet that enduring playfulness has coincided with a more serious cultural shift.

During the 1960s and ’70s, college-educated newcomers, artists and others looking for lives outside the conventional American mold arrived in Aspen. Thompson became the most famous face of the Freak Power political movement, but Lookabill describes a broader “changing of the guard” as politically engaged newcomers pushed for environmental protections, zoning restrictions and greater influence over Aspen’s future.

The $75-a-month Aspen

Tim Mooney arrived in time to see it all.

He moved to Aspen in 1970 and rented a downtown log cabin for $75 a month. More than half a century later, he still lives there.

Mooney went on to teach skiing on Aspen Mountain for 25 years, worked as a tour manager on the road with singer-songwriters Jimmy Buffett and John Denver and eventually became a real estate broker at Christie’s International who today jokes that the Aspen Mountain gondola is his office.

But back in the ‘70s, he served drinks at J-Bar, the historic watering hole inside the Hotel Jerome, a luxury Aspen landmark dating to 1889 that has long drawn an eclectic mix of locals, celebrities and larger-than-life characters, including Hollywood stars such as John Wayne and Gary Cooper.

“I was kind of like Hunter’s bartender for a long time,” he says, remembering Thompson arriving around noon with his mail and sometimes remaining through dinner. Jack Nicholson would stop in to hang out with Thompson, Mooney recalls, as would celebrities including Michael Douglas and Clint Eastwood.

The characters drawn to Aspen weren’t limited to writers and movie stars. Mooney remembers serious cyclists, “incredible dedicated fly-tying maniacs” and rock climbers he describes simply as “monsters in the mountains.”

And despite Aspen’s current median single-family home value sitting north of $13 million and average winter hotel rates that can top $1,000 a night, he still sees younger versions of that same type arriving today.

“There are people who are coming here, like I did out of college, willing to do odd jobs, willing to live with roommates,” Mooney says, if it means being able “to be the first one in the gondola line on a powder day.”

They sacrifice other parts of life, he says, for the mountains and the “spiritual vibe of being in this magic valley.”

“You can live between the lines,” he says. “You can live on the fringes.”

The more Aspen changes

Wealth and culture have long coexisted here. But Lookabill traces a significant shift toward Aspen’s modern luxury identity to the 1980s, when larger companies increasingly began investing in the town.

Celebrity culture changed, too. Lookabill says famous visitors once came to Aspen looking to fit in with the locals and “not necessarily wanting to be seen,” while later decades brought more ostentatious versions of celebrities and influencers who wanted “to be seen, to be photographed.”

The old ski-bum existence wasn’t always as carefree as its mythology suggests, either.

“People worked their butts off to try to make ends meet, even back then,” says Lookabill, who recalls working multiple jobs herself after moving to Aspen 26 years ago.

Today, fewer businesses are locally owned, she says, while many workers live farther down the Roaring Fork Valley and commute into town. But Lookabill rejects the idea that the local community has vanished in the face of Gucci, Chanel and Kemo Sabe. After all, Aspen also has its own volunteer-run Aspen Thrift Shop, where discounted items are readily available.

What one sees in the media is “the peak season,” she says. “And you’re seeing the visitors. You’re not seeing the year-round local community. We’re doing our own thing on a regular basis.”

Hiding in plain sight

Some of that “own thing” is hiding in plain sight.

In Aspen’s residential neighborhoods, you’re just as likely to see the “pickle car” — the eccentric Volkswagen Beetle that once served as a delivery vehicle for now-defunct local sandwich shop Johnny McGuire’s — as you are a Ferrari.

Near Buttermilk Mountain sits the Magic Mushroom House, the famously unconventional home Andre Ulrych began building in 1973, inspired in part by psychedelic mushrooms and LSD. The nearly 6,000-square-foot house took six years to complete, with curving walls, mismatched windows and virtually no corners.

On Main Street, the laid-back Grateful Deli wraps a neighborhood sandwich shop in tie-dyed Grateful Dead iconography, while no-frills hangouts like BUCK and the Woody Creek Tavern (where Thompson was once a regular) offer an alternative to Aspen’s more polished après-ski scene.

For Watkins, none of this exists in opposition to Aspen’s luxury side. In fact, he argues that culture has always coincided with wealth as part of what made the town desirable in the first place — adding a “layer of depth” that other resort towns simply can’t replicate.

That idea traces back to the 1940s, when the Paepckes envisioned the postwar town as a gathering place for artists and intellectuals, organized around a “mind, body and spirit” philosophy that became known as the Aspen Idea.

What made Aspen a sought-after place to live for “the more privileged class” is the fact that the town has “an embarrassment of riches of culture,” Watkins says, noting the town’s high concentration of music, art, dance and performances.

The mountains also remain an essential element of the attraction, drawing what Watkins calls “this adventurous crowd that cares about nature and skiing and hiking,” as well as creative people who come here “to think bigger.”

The next generation

During a recent afternoon at Aspen Collective, a young artist was preparing work for an upcoming exhibition when Watkins spotted him and turned with an important question.

Was he, by chance, a freak?

The artist didn’t hesitate.

“Yeah, no doubt.”

Watkins smiles, noting that “all the freaks are going to be out” at the following night’s opening featuring young local artist Fat Chance.

“I kind of dedicated my life to trying to keep the history alive,” Watkins says, but then also “forge a future that’s fun and kind of embraces this radical countercultural existence that’s always been here.”

That future is unlikely to look exactly like Thompson’s Aspen. The economics are different. The characters are different. Even the freaks are different.

But maybe that’s just what makes Aspen Aspen.

“The more important, meaningful, exciting things in life are still happening here,” he says. “You just have to look a little harder.”

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