Bobby Osborne was a pioneering bluegrass musician, renowned for his work as part of the Osborne Brothers, alongside his younger brother Sonny. Born on December 7, 1931, in Roark, Kentucky, Bobby and his family moved to Hyden after their house burned down, and later settled near Dayton, Ohio. Bobby served in the United States Marine Corps during the Korean War, after which he joined forces with his brother Sonny and Jimmy Martin to perform at various radio stations.

The Osborne Brothers became known for their innovative approach to bluegrass music, incorporating unorthodox instrumentation and vocal harmonies. Their first major success came with the single "Ruby Are You Mad" in 1956, which marked the first use of twin banjos in a bluegrass recording. They achieved further fame with their 1967 hit "Rocky Top," a song that became a bluegrass standard.

Bobby Osborne's distinct mandolin playing and high lead vocals were central to the group's sound. The Osborne Brothers were active from 1953 until Sonny's retirement in 2005. Bobby continued to perform and record, celebrating milestones such as the 50th anniversary of "Rocky Top" and receiving his first solo Grammy nomination later in his career.

Bobby Osborne passed away on June 27, 2023, at the age of 91, leaving behind a legacy as one of the most influential figures in bluegrass music.