Born as George Miles in 1945, he started out as a teenage prodigy. At the age of twelve, he began playing drums in his father’s jazz combo, The Bebop’s, in Omaha, Nebraska. In those early days, his career included stints with such luminaries as the Ink Spots (who are credited with inspiring the “doo-wop” vocal genre of the 1950s), The Delfonics, Ruby & The Romantics, Otis Redding and, last but not least, Wilson Pickett in 1966. In 1967, young blues-guitarist Mike Bloomfield (Paul Butterfield’s Blues Band, Al Kooper, Bob Dylan) attended a Wilson Pickett show at the RKO Theatre in Brooklyn, New York, and was impressed by Miles inimitable bottom-heavy drumming style.
Afterwards, Bloomfield successfully recruited Miles for his own brand-new psychedelic blues-rock band, the Electric Flag. Bloomfield's subsequent departure left the drummer in control. In the wake of a disappointing second album, Miles retained its horn section for his next venture, the Buddy Miles Express. During these days, he had also become friends with Jimi Hendrix. Both of them had played the Monterey Pop Festival in 1967. Later on, it was Miles who laid down a solid backbeat for "Rainy Day" and "Still Raining" on Jimi’s Electric Ladyland. Hendrix, in return, produced and wrote some sleeve-notes for Expressway To Your Skull, the first hard driving, electric soul album by the Buddy Miles Express. In 1969, the Jimi Hendrix Experience broke up, and Miles replaced the former Experience drummer Mitch Mitchell. Arguably the first true "black rock band" - long before Living Colour - Jimi Hendrix's Band Of Gypsys debuted at Bill Graham's Fillmore East on New Year's Eve 1970.