Hollywood in Aspen: Why a small Colorado mountain town plays host to the silver screen’s elite

When someone who’s never been to Aspen hears the town’s name, they often associate it with glamour, money and celebrities. Whether this is an accurate perception or not, it’s one that our small mountain town has garnered.

Spend a busy weekend here over the holidays and it’s easy to see how we got that reputation. The streets are filled with gorgeous people in lush furs and big sunglasses. Behind the shades may be singer Mariah Carey, here to enjoy Christmas with a significant other. Or it’s Paris Hilton, waiting patiently for her boyfriend Chris Zylka to whip out a 20-carat ring at the top of Aspen Mountain and ask for her hand in marriage. It could be Will Smith, enjoying time with his family or buffing up for his latest role in a new hit movie. Maybe it’s even Charlie Sheen, posting bond after spending a brief stint in Pitkin County Jail. Or, perhaps it’s Elton John, Sting, Leonardo DiCaprio or Kanye West and Kim Kardashian. The list of possibilities is endless.

Along with the A-list celebs who drop in briefly for a special occasion, there are also those who choose to make their first or second (or third or fourth) home in Aspen. From John Denver and John Oates to Jack Nicholson and Hunter S. Thompson, many stars have planted roots here. Like any full- or part-time local, there was something about this quaint town of 6,000 people that pulled them in and never let them go.

How it all started

Hollywood and skiing have always had a rather symbiotic relationship. After the 1936 Olympics, in which alpine skiing was included for the first time, the downhill sport became the new trendy activity, particularly among the stars. Businessmen and investors starting ski resorts realized how important star power would be in getting regular folk to the slopes, according to a history column in the Aspen Times Weekly from 2015. In Sun Valley, Union Pacific Railroad Chairman Averrell Harriman invited celebrities like Gary Cooper, Claudette Colbert and Norma Shearer to ski the resort. Walt Disney also brought stars to his investment, Sugar Bowl in California. The investors building up Aspen used this strategy, as well. They invited film star Jack Oakie and his wife out for a weeklong vacation in 1941, shortly after the Aspen Ski Club hosted the national alpine ski championships. Apparently, the trip went very well. Oakie loved Aspen and promised to return with more Hollywood friends in the months to come. During World War II, much of the focus moved away from ski resorts, but after the war there was even more interest.

Gary Cooper is often considered Aspen’s original celebrity because he was one of the first to stay here for an extended period of time. He was introduced to the town by friend Friedl Pfeifer. They originally went to Sun Valley, but Pfeifer experienced Aspen during training with the 10th Mountain Division at Camp Hale. He was hooked and spent much of his time there after that. When he showed the place to Gary Cooper and his wife, they too swooned and decided to build a house.

The town and ski resort in Aspen began hosting more events that drew in Hollywood types. These included the Goethe Bicentennial in 1949, FIS in 1950 and even the Winterskol Parade in 1953, which actors Lana Turner and Lex Barker were formerly invited to. From there, the flood gates between Hollywood and Aspen opened, and they haven’t shut since.

Aspen Film’s Hollywood connection

Perhaps one of the truest signs that Hollywood’s connection to Aspen is still alive and well is through the success of the nonprofit Aspen Film. Founded in 1979, the organization puts on several film festivals and other movie events throughout the year and also has an education program.

A very popular event that Aspen Film hosts at the end of each year is the Academy Screenings, in which some of the best and most notable films of the year are screened over a week-and-a-half period. This film festival started in 1992 as a way for industry folk who were voting members of the Academy of Motion Picture Arts and Sciences, and several other applicable guilds, to see and vote on the films up for awards while vacationing in Aspen. All guild members have always been able to go to the films for free. The public has access to the screenings but have to pay for admittance. At the start, Aspen Film screened only three or four movies. Last year’s festival brought in 29 feature films.

Aspen Film has gone through some changes in the past year. One was hiring Susan Wrubel as its new executive director. Wrubel has a storied career in the industry. She said the nonprofit’s relationship with Hollywood is strong because those involved in the organization have many ties to it. Not only does she have connections but board chairman Ryan Brooks and his wife, Jessica Latham, are active producers in the industry, along with three other board members.

“Aspen Film’s connection with Hollywood these days is deeper than it has been for a while,” Wrubel said. “Our collective relationships offer us access to amazing people, material and films, often offering us unique opportunities to present early glimpses at films and filmmakers in advance of theatrical release.”

More than those on the silver screen

The people on screen and onstage aren’t the only ones in the biz that enjoy the Aspen lifestyle. Over the years, producers, directors, writers and other industry leaders have also found a connection with the mountain town.

Peter Gruber, the chairman and CEO of Mandalay Entertainment who owns a large ranch in the valley, was quoted in a Vanity Fair article saying, “Hike through this place and it’s like God has created candy for your eyes.” He said the town is great because there’s so much going on, from dining to entertainment, but the best part about it is being left alone.

That privacy, that calm serenity that Aspen emanates, is one of the qualities that originally enticed Michael Davis, a Los Angeles-based producer and the founder of N3 Media, an entertainment and sports focused digital agency based in L.A. and New York.

Davis first came to Aspen nearly two decades ago when he started climbing. He typically gets to the area three to four times per year, in the spring, summer and fall, and stays with good friends. With the direct flights during the high season, he said it’s seamless to get to the mountain town. Davis likes many different aspects of an Aspen trip (including the fact that it’s almost always sunny), but one of his daily priorities is being outside and getting active.

“You wake up everyday and you do something physical,” he said. “Then you go have a nice lunch, a nice dinner, a nice bottle of wine, and wake up and do it all over again.”

The industry veteran said when he’s in Aspen it’s common to run into friends from the industry who visit from L.A., New York City and Miami. However, he finds it’s not just industry-specific. Successful people, in general, seem drawn to Aspen, probably because it can be quite expensive to travel and stay here.

The beat goes on

As long as Aspen has had skiing, it’s had celebrities. Some may think it’s gotten glitzier over the years, so much so that it can be unappealing. But the connection between Hollywood and our beloved mountain town is older than the first single-seat chairlift that went up Aspen Mountain.

Love it or hate it, Hollywood will most likely always have a place in the town where the beer flows like wine.