ABOUT US
THE BAND: Kris Bergman (Bass), Dan Flesher (Mandolin/Vocals), Kevin Jackson (Drums/Vocals), Cowboy Bob (Songwriter/Guitar/Vocals), and Wally Benjamin (Harmonica/Vocals)
Hello!
Cowboy Bob and Gypsy Dust are now booking spring, summer, and fall 2026 performances. We offer everything from a full five-piece band, to a trio or a duet — what ever best suits your venue.
Recognized as one of Montana’s premier Western Swing bands, Cowboy Bob and Gypsy Dust deliver a high-energy mix of original Western Swing alongside classic favorites from the 1930s, 40s, and 50s. The band is known for crowd-pleasing shows, strong musicianship, and authentic Western sound.
Highlights
Critically acclaimed throughout Montana
Performed live on KGLT Radio (Bozeman) to their worldwide audience
Multiple live albums available on Spotify, Apple Music, YouTube Music, Pandora, and all major streaming platforms
Featured Videos & Music of Cowboy Bob’s Original Music
“Buffalo Range” performed at the Hangar Sessions Studio in Helena , Montana
Live KGLT (Bozeman, MT) performance of “One Toe in the Stirrup” and Sweet as a Peach
Live at the Top Hat Lounge (Missoula) performance of “Wild About You”
Notable Montana Venues
The Top Hat (Missoula), Rialto Theater (Bozeman), Old Saloon (Emigrant), Covellite Theatre (Butte), The Westerner (Gallatin Gateway), The Celtic Cowboy (Great Falls), The Murray Bar (Livingston), The Original Montana Club (Helena), KGLT Radio, and many more — including appearances at the National Western Music Festival.
Learn More
We would love to bring this exciting Western Swing experience to your venue.
Please reach out to discuss availability, pricing, and production needs.
Best regards,
Cowboy Bob and Gypsy Dust
Booking & Performance Inquiries: CowboyBob251@gmail.com