ABOUT US
THE BAND: Kevin Jackson (Drums/Vocals), Wally Benjamin (Harmonica/Vocals), Cowboy Bob (Songwriter/Guitar/Vocals), Kris Bergman (Bass), and Dan Flesher (Mandolin/Vocals).
Cowboy Bob and Gypsy Dust Are Now Booking
Fall AND Winter 2026/2027 Performances
Seasoned in countless western honky-tonks, the band Cowboy Bob and Gypsy Dust personifies the genuine western cultural and musical experience by bringing the honky-tonk into the concert hall.
Cowboy Bob is a real cowboy who grew up riding horses and driving cattle on a genuine working cattle ranch. He and his band members, veterans of thousands of honky-tonks, have been playing western swing music for years.
You cannot find a band more authentic than this one! This is “The Real McCoy.” If you want a genuine western cultural experience, hire this band to bring the honky-tonk into your concert hall, or to bring the concert hall into your honky-tonk.
Recognized as one of Montana’s premier western swing bands, Cowboy Bob and Gypsy Dust deliver a high-energy mix of original western swing music 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 to a worldwide audience on KGLT Radio (Bozeman)
Appearances at the International Western Music Festival
Four albums available on Spotify, Apple Music, YouTube Music, Pandora, and all major streaming platforms.
FEATURED VIDEOS OF COWBOY BOB’S ORIGINAL MUSIC
“Buffalo Range” performed at the Hangar Sessions Studio in Helena, Montana
Live KGLT Radio (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 Lounge (Missoula)
Rialto Bozeman Theater (Bozeman)
Old Saloon (Emigrant)
Covellite Theatre (Butte)
The Westerner (Gallatin Gateway)
The Big Sky Room of the Montana Heritage Center (Helena)
The Celtic Cowboy (Great Falls)The Murray Bar (Livingston)
The Original Montana Club (Helena)KGLT Radio, and many more — including appearances at the Interational Western Music Festival.
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 Benda
EMAIL: cowboybob251@gmail.com
PH: 406-465-2162