Born in Leslie County, Kentucky, Osborne is known primarily for his collaborations with his brother Sonny Osborne in their band, the Osborne Brothers. Osborne grew up helping his dad stock his granddad’s general store and absorbing the songs on the Grand Ole Opry, eventually dropping out of high school to form a band with his brother, Sonny. He was a pioneer in conceiving the now-popular “high lead” vocal trio concept. He has released many recordings since the 1950s. The Osborne Brothers recordings of “Rocky Top”, and “Kentucky” were named official state songs of Tennessee and Kentucky, respectively. Osborne was drafted into the U.S. Marine Corps in 1951 and served in the Korean War. He was wounded in action and received the Purple Heart.
“Bobby knew nothing about bluegrass music and had never heard of Bill Monroe and the Bluegrass Boys. He was listening to the Grand Ole Opry one night on WSM radio. He liked the sound of that banjo, and found out later on it was Earl Scruggs playing a tune called “Cumberland Gap.” From then on, he became interested in that music. He appeared on many shows with his musical hero, Ernest Tubb, playing guitar and singing. Ernest Tubb suggested that Bobby play the mandolin to compliment his high tenor voice. He began to play the mandolin and It remained one of his main instruments for the rest of his career