Considered a child prodigy, he began playing drums when he was three, piano at five and joined the Musicians Union when he was nine. Miles played drums professionally from the age of ten, including sitting in with the Woody Herman Orchestra. At the age of 12, he recorded his first album as a leader on drums, leading a sextet that included pianist Duke Jordan.

As a teenager, he studied classical piano and soon switched instruments. Originally a bop-oriented player, Miles leaned towards fusion by the late 1960s, often playing electric piano and synthesizer. He led Silverlight for several years (his sidemen at various times included Woody Shaw, John Abercrombie and Al Di Meola), worked as Roberta Flack's musical director in the early 1980s and became a studio musician in New York. Although he periodically appears on records, Miles has not yet lived up to his great potential as a major jazz improviser.