A jazz singer, Jeffries was known for his 1940 recording of “Flamingo” with Duke Ellington — which sold millions of copies. It “was, and is, a jazz classic,” says music critic Don Heckman. “Jeffries’ rich-toned ballad style resonated in the work of such male jazz singers as Johnny Hartman, Joe Williams and even Sammy Davis Jr. for decades.” He sang with the Duke Ellington Orchestra for several years, but is better known for getting funding to produce a western film starring a singing black cowboy — himself. Born Umberto Alexander Valentino, there was some confusion over his racial identity, which he used to his advantage. “Look at my blue eyes, look at my brown hair, look at my color. What color do you see? My mother was 100 percent white, my father is Portuguese, Spanish, American Indian, and Negro. How in the hell can I identify myself as one race or another?”
When singing with Duke Ellington, Jeffries used makeup to make himself blacker, to fit in better with the band. When he married actress and burlesque legend Tempest Storm, he identified himself as white. “For all these years I’ve been wavering about the color question on [forms],” he said in 1959, when he married Storm, who was white. “Suddenly I decided to fill in the blank the way I look and feel.” Of course, he identified as black when he made the film, 1937’s Harlem on the Prairie, billed as the first “all-colored” western musical. That made Jeffries the first (and, still, only) starring “singing black cowboy” in Hollywood Western history. It was successful enough to spawn several more movies, including Two-Gun Man from Harlem (1938), Harlem Rides the Range (1939), and The Bronze Buckaroo (1939). He loved providing a role model for kids. “Little children of dark skin — not just Negroes, but Puerto Ricans, Mexicans, everybody of color — had no heroes in the movies,” he said in 1998. “I was so glad to give them something to identify with.” After the movies ended, he opened a night club in Paris, and returned to the U.S. in the 60s. Jeffries died May 25, from heart failure. He was 100.