Michael Cain first started playing the piano at the age of four and was quickly improvising and composing. The following year he began studying classical music, although by the age of ten it was jazz that became predominant, as well as an interest in integrating several kinds of popular music.
Michael moved to New York in 1990 and began performing with many members of M-Base, a Brooklyn-based collective of musicians, initially with Greg Osby and later with Robin Eubanks and Lonnie Plaxico among others. That same year he recorded his first CD as a leader, Strange Omen, for the Candid label, a trio recording that features Glen Velez on hand percussion and Bruce Saunders on guitar. Later that year Michael started playing with Jack DeJohnette and joined his group Special Edition.