He also played clarinet and oboe for the Boston Civic Symphony Orchestra in 1926.
Holmes began playing also saxophone at age 16 and emulated the style of his childhood friend, Johnny Hodges.
After moving to New York City he worked for a variety of groups, including Luis Russell in 1928.
He would work with Russell again a few times and in 1932 joined the Mills Blue Rhythm Band.
He was in the John Kirby's Sextet, Cootie Williams' Orchestra, and Louis Armstrong's band for much of the next two decades.