Winold Reiss was arguably the best (and the best-known) artist historically associated with Montana railroading. Reiss first visited Montana in 1920 and immediately fell in love with the place, while simultaneously becoming fascinated with the Blackfeet Nation and its culture. Before long, that infatuation translated into a business arrangement with the Great Northern, which frequently used Blackfeet themes in its advertising. For a quarter century, Reiss painted handsome, modernistic portraits of the Blackfeet for the GN, which the railroad used on its calendars, dining-car menus, and other promotional materials. Today, the Reiss material is rare and highly collectable ... and just as appealing as ever.
Reiss spent a fair amount of time on the Blackfeet reservation and in Glacier, especially during his earlier years ... and during the mid-1930s he actually operated an art school in the former St. Mary Chalet buildings, hiring local Blackfeet to serve as models for his students. Nationally, his best-known commission was for an amazing series of murals that hung in Cincinnati's railway station. Today, a few of those murals are at the Cincinnati airport, looking woefully out of place.
Here's one of the last paintings Reiss did for the Great Northern ... a portrait of Floyd Middle Rider, completed in 1948. That's Chief Mountain in the background.