He began playing the piano in school and by the early 1930s worked with Lucky Millinder, Tiny Bradshaw and later the Mills Blue Rhythm Band.
He appeared and recorded with many swing era orchestras including Duke Ellington, Fletcher Henderson, and Mills Blue Rhythm Band, before returning to Baltimore in the 1942 and beginning a career as a lion tamer.
The 1930s saw him playing with Bobby Neal (1931) and the Mills Blue Rhythm Band; he was both a performer and an arranger for the Blue Rhythm Band from 1932 to 1936, when Lucky Millinder replaced him.
It started life as the Coconut Grove Orchestra, changing to Mills Blue Rhythm Band when Irving Mills became its manager in 1931.
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Irving Mills revived the Mills Blue Rhythm Band name for two recording sessions in 1947 under the guidance of Van Alexander.
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In 1934 and 1935, Bailey was playing with the Mills Blue Rhythm Band and in 1937 he was a session player for Midge Williams and Her Jazz Jesters.