Born William Thomas Dupree, 4 July 1910, New Orleans, (Dupree's birth date is the matter of some conjecture and is sometimes listed as 23 July 1909). Orphaned in infancy, Dupree was raised in the Colored Waifs Home for Boys until the age of 14. After leaving, he led a marginal existence, singing for tips, and learning piano from musicians such as Willie Drive-'em-down Hall. Dupree also became a professional boxer, and blended fighting with hoboing throughout the 30s, before retiring from the ring in 1940, and heading for New York. Initially, he traveled only as far as Indianapolis, where he joined with musicians who had been associates of Leroy Carr. Dupree rapidly became a star of the local black entertainment scene, as a comedian and dancer as well as a musician. He acquired a residency at the local Cotton Club, and partnered comedienne Ophelia Hoy.
In 1940, Dupree made his recording debut, with music that blended the forceful, barrelhouse playing and rich, Creole- accented singing of New Orleans with the more suave style of Leroy Carr. Not surprisingly, a number of titles were piano/guitar duets, although on some, Jesse Ellery's use of amplification pointed the way forward. A few songs covered unusual topics, such as the distribution of grapefruit juice by relief agencies, or the effects of drugs.
Dupree's musical career was interrupted when he was drafted into the US Navy as a cook; even so he managed to become one of the first blues singers to record for the folk revival market while on leave in New York in 1943. Dupree's first wife died while he was in the navy, and he took his discharge in New York, where he worked as a club pianist, and formed a close musical association with Sonny Terry and Brownie McGhee.