 Amsberry was born in 1928 in the small town of Boring, Oregon, the third child of Ernest and Cassie Amsberry.Amsberry graduated from Franklin High School in Portland, where he was a friend and classmate of Johnnie Ray.Amsberry was musically inclined from a young age, and in 1954, began an entertainment radio program in Portland titled "Uncle Bob's Squirrel Cage" on the KEX radio station.