Jeffries, a deep baritone, sang with Duke Ellington in the 1940s. His most famous song, "Flamingo", sold over 50 million copies.
Through a series of low-budget westerns, in which he played a singing cowboy, he soon became known as the "Bronze Buckaroo" by fans who flocked to his films. In a time of American racial segregation these films played only in theaters catering to African Americans audiences, though Jeffries was/is not African-American. The films can be found on video and are titled, "The Bronze Buckaroo", "Harlem Rides the Range", "Two Gun Man from Harlem", and "Harlem on the Prairie".