Bill Bailey's father was a preacher in a "Holy Roller Church" and started dancing there. Bailey was older brother to actress and singer Pearl Bailey and second cousin to Bob (William) Bailey, son to Joseph James and Ella Mae Bailey. Bill sang and danced professionally, sometimes dancing with Blanche Calloway (Cab Calloway's sister). Was said to be a Bill "Bojangles" Robinson and King Rastus Brown student who could really move his feet and Bojangles forbid him from doing any of his routines.

Danced in the kitchen scene in 'Cabin in the Sky film'. Made some other Films and can be seen Tap Dancing in the 1955 tribute to Bojangles 'Harlem Variety Revue' an interesting side note to this while it was done many years before, is he finishes his act with a 'Moon Walk' off the Stage. Bailey was in temporary reitrement in 1965