Hebb was born in Nashville, Tennessee. His parents, William and Ovalla Hebb, were both blind musicians. Hebb and older brother, Harold Hebb, performed as a song-and-dance team in Nashville beginning when Bobby was three and Harold was nine. Hebb performed on a TV show hosted by country music record producer Owen Bradley, which earned him a place with Grand Ole Opry star Roy Acuff. Hebb played spoons and other instruments in Acuff's band. Harold later became a member of Johnny Bragg and the Marigolds. Bobby Hebb sang backup on Bo Diddley's "Diddley Daddy". Hebb played "West-coast-style" trumpet in a United States Navy jazz band, and replaced Mickey Baker in Mickey and Sylvia.[2