In 1920, after having served in the Navy for 18 months, he joined a jazz formation named the Carolina Five, and remained a member for the next three years, playing small clubs and boat rides all around New York City.

After leaving the band at the age of 19, Miley briefly toured the Southern States with a show titled The Sunny South, and then joined Mamie Smith's Jazz Hounds, replacing trumpeter Johnny Dunn.

With fellow band member, trombonist Joe "Tricky Sam" Nanton, Miley developed the "wah-wah" sound that characterized Ellington's early "jungle music" style.

In interviews, former co-musicians such as Ellington, Nanton, Hardwick, and Harry Carney spoke fondly of Bubber Miley's carefree character and joie de vivre, exemplified in numerous anecdotes.

[1] After returning to New York, he recorded with groups led by King Oliver, Jelly Roll Morton, Hoagy Carmichael, Zutty Singleton and with Leo Reisman's society dance band.