Born in Swindon, England, in 1934, Bailey learned to play drums as a child, studying formally from age seven.
[1] In Sydney, he played with Bryce Rohde and the Australian Jazz Quartet, backing musicians such as Dizzy Gillespie and Sarah Vaughan.
This trio played with Jimmy Witherspoon, Ben Webster, and Gene Ammons for the Jazz Workshop in San Francisco.
In 1963, he moved to Los Angeles to play with the Victor Feldman Trio, returning to San Francisco the following year to record Jazz Impressions of A Boy Named Charlie Brown with Guaraldi.
His later work includes time with Richie Cole, Jimmy Rowles, Red Mitchell, Stefan Scaggiari, Joe Pass again, Ron Affif, Weslia Whitfield, and John Pisano.