The Osbornes were born in Roark, Kentucky, on Jack's Creek, but they moved to Hyden after their house burned down. They then moved near Dayton, Ohio, where they grew up and performed as entertainers in southwestern Ohio. In 1952, during the Korean War, Bobby was drafted and served in the United States Marine Corps. Sonny went to work with the "Father of Bluegrass Music" Bill Monroe. Following Bobby's discharge, the Osbornes teamed up with Jimmy Martin, performing at radio stations WROL in Knoxville, Tennessee and WJR in Detroit, Michigan. At their only session together, on November 16, 1954, the Osbornes and Martin recorded six songs for RCA Victor. In late 1955, the Osbornes left Martin and moved to Wheeling, West Virginia, where they performed on WWVA Jamboree until Christmas, together with Charlie Bailey. They returned to Dayton in early 1956 playing the local clubs with guitarist Enos Johnson. When Johnson left, the Osbornes added guitarist Red Allen and fiddler Art Stamper to form a new group.