Bailey was born in Portsmouth, Virginia. He studied drumming at the Music Center Conservatory in New York City after he served in the Air Force during World War II. From 1951 to 1953, he played with Herbie Jones, then with Johnny Hodges and Curtis Fuller. He also played with Billy Taylor, Lou Donaldson and Curtis Fuller. He played on many sessions with Gerry Mulligan between 1954 and 1968. In the 1960s, he also played alongside Clark Terry, Grant Green and Roger Kellaway. He retired from music in 1969 and became a flight instructor. He worked in New York music education from 1973 to 1973. He was also involved with The Jazzmobile. Wikipedia
