Cowboy from Brooklyn (1938)

Brooklyn crooner Elly Jordan and his bandmates end up broke at a Wyoming dude ranch run by Jane Hardy. Singing for his supper there, Elly is heard by Broadway booker Roy Chadwick, who mistakes him for a genuine cowboy and decides to make him a star. The fact that Elly is terrified of animals (including horses) and doesn't know the first thing about the West makes his big break tough to pull off.