In 1924, Armstrong left King Oliver's Jazz Band to join Fletcher Henderson's Orchestra in New York.

[2] Within a month, Armstrong extended an invitation for Buster Bailey to join him as a member of Henderson's band.

[3] In New York during the late 1920s, Buster Bailey became a highly respected sideman with Perry Bradford and others, and appeared on numerous recordings playing both the clarinet and the soprano saxophone.

After his return, Bailey performed with several other jazz musicians, including Edgar Hayes and Dave Nelson.

In 1934, Bailey briefly returned to Fletcher Henderson, but by the end of the year he had settled down as a member of the John Kirby Band.

[2] 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.