09/08/2025
What a fantastic story on Dianna Olson and The Cowboys Bar & Museum. Thank you Di for all you do for MCA and for your support of Real Country Montana!
Dianna Olson, Cowboy’s Bar
Looking back on her childhood in Black Eagle, Montana, Dianna Olson remembers the small town as the “coolest place ever” to be a kid. “We didn’t have much money but our dad, who was a machinist, made sure we had fun—building us go karts and sleds,” she says. “My mom was a ‘stay-at-home’ mom who baked and sewed all our clothes, and the school we went to, Collins School, was small with only 100 or so students total and one class per grade. We knew everybody.”
It was a bit of a shock when she advanced to C.M. Russell High School in Great Falls, just a few miles away from Black Eagle. “It seemed gigantic,” Dianna says. “I became a bookworm, withdrawn and quiet. Being around all those people kind of freaked me out!”
In high school, her first job was as a carhop at the A&W. It taught her a valuable lesson in how to overcome shyness. “It changed me a lot. I found that the best way to become more outgoing is to get out there and interact with people.”
As a bartender at the Black Eagle County Club and the adjoining Wally’s World bar for 30 years, Dianna had ample time to expand those people skills. For the past 13 years, she has been the manager of the legendary Cowboys Bar and Museum in Great Falls.
“I fell in love with this place—the history of it and the people who come in here are just amazing,” said Dianna, “It’s sort of like Cheers, where everybody knows your name.”
Owned by the Montana Cowboys Association, the authentic log cabin has more than 500 displays of artifacts that reflect the historical importance of Montana’s Western heritage. Relics of that vibrant past include a gun collection and authentic tools used by cowboys and cowgirls, stockmen and pioneers.
Dianna, who still resides in Black Eagle, is especially fond of one of the museum’s displays.
“Using wood lathe and metal work, my dad created a replica of a covered wagon and when he died, it was donated to the museum. Looking at it reminds me of what a great childhood I had.”