Miles was born in Indiana but moved to California at a very young age, where he started his career as a singer in Richmond, San Francisco.
He perfected his singing technique at the School of Natural Voice at Los Angeles tutored by Patricia Warner, and contemporarily completed his formal studies in musical theory.
Miles subsequently worked as both an individual artist and vocalist supporting musicians such as Edwin Starr, José Feliciano, Big Joe Turner, Johnny Otis, Eddie Vinson and Jimmy "Bo" Horne.
Following a gig at the Scimmie Jazz Club in Milan, he was invited by Renzo Arbore to participate in his popular TV show Quelli della notte on Rai 2.
Zucchero's most successful hits like "Senza una donna" ("Without a Woman"), "Hey Man", "Baila", "Ahum" include Miles' participation.