Cirillo studied at the New York Conservatory of Modern Music (1948–50) and the Manhattan School of Music, and played with Chubby Jackson and Bill Harris in the early 1950s. In 1954 he began working with John LaPorta, Teo Macero and Charles Mingus as part of the New York Jazz Composers Workshop. The following year, he led a session with Mingus, Macero, and Kenny Clarke, which was later reissued under Mingus's name as Jazz Composers Workshop. The piece "Transeason" on this album, composed by Cirillo, makes use of serialism, one of the earliest manifestations of this compositional technique in jazz. He also recorded with LaPorta and with Johnny Mathis in the 1950s.