Oldest Opry Solo Member & Bluegrass Great Bobby Osborne Dies

It is a mournful week in country and bluegrass as we’ve lost two mandolin playing legends, two influential titans of the bluegrass discipline, and two of the oldest members of the Grand Ole Opry in a span of five days. On June 23rd, Jesse McReynolds passed away at the age of 94, making Bobby Osborne the Opry’s oldest solo member. Now Bobby Osborne has also died, passing at the age of 91. Buck White, who is part of Grand Ole Opry member group The Whites, is still alive at 92.

Both Jesse McReynolds and Bobby Osborne were known for playing in groups with their brothers, and bringing blood harmonies to bluegrass music. Bobby Osborne’s younger brother Sonny passed away in October of 2021 at the age of 84, but Bobby continued to perform almost up to his death with his band the Rocky Top X-Press, named after the song “Rocky Top,” written by Felice and Boudleaux Bryant, but made famous by the Osborne Brothers.

Bobby Van Osborne was born December 7, 1931 in Thousandsticks, Kentucky. From an early age the two brothers were performing music together. Bobby was drafted into the Marine Corps to serve in the Korean War, which put the brother duo on pause. But after Bobby’s return from the war with a Purple Heart, the two brothers went to work for the “King of Bluegrass” Jimmy Martin, and later moved to Wheeling, West Virginia to become mainstays on the Wheeling Jamboree, which after the Grand Ole Opry was the oldest country music radio show.

After the Osborne Brothers recorded some music successfully for Gateway Records, the Osborne Brothers were later signed to MGM Records, and by the late 50’s, they were considered one of the premier acts in all of bluegrass, known for their spellbinding musicianship, and Bobby’s Osborne’s tenor. By 1964, they had received an invitation to become members of the Grand Ole Opry—something that wasn’t easy to win in that era since as a bluegrass act you needed the blessing of Bill Monroe.

The sheer musicianship of the Osborne Brothers won them many fans well beyond the country and bluegrass realm. They helped make bluegrass cool, especially after they released “Rocky Top” on Christmas Day in 1967, and the song enjoyed ubiquitous popularity that is still around today. Of course like all bluegrass songs in country, “Rocky Top” struggled to become a “hit” on radio, only reaching #33. But among the populous in Tennessee and beyond, “Rocky Top” became synonymous with bluegrass and Tennessee. It is one of the most widely-known and beloved banjo songs in history, performed on the banjo by the late Sonny Osborne, and eventually became a Tennessee State song.

The Osborne Brothers were known for other songs as well, including “Up This Hill & Down,” “Ruby Are You Mad,” “Tennessee Hound Dog,” and “Midnight Flyer” written by Paul Craft, which was later recorded by The Eagles on their On The Border album, speaking to the Osborne Brothers influence across popular music. Their song “Kentucky” also became a state song of Kentucky. Sonny and Bobby Osborne were inducted into the International Bluegrass Music Hall of Fame in 1994.

As time went on the Osborne Brothers helped bluegrass evolve. Unlike other bluegrass groups, they would play with instrumental amplification as opposed to just into microphones, or would include outright electric instruments, and sometimes drums. This sparked a little controversy in the bluegrass realm, but opened up the music to new audiences. Nearly a decade before Earl Scruggs would make headlines playing an anti-War protest in 1969, the Osborne Brothers played Antioch College in 1960, bringing bluegrass to a younger and different generation.

Bobby’s brother Sonny was forced to retire in 2005 after rotator cuff surgery rendered him unable to play the banjo at peak performance, but Bobby was a regular performer on the road and at the Grand Ole Opry. Along with being the oldest Opry member, Bobby Osborne was also one of the oldest legends in country music.

It’s truly the end of an era with the passing of Bobby Osborne and Jesse McReynolds. Some of the oldest living links to country music’s past are now gone. But their music and its influence will endure.

Editor’s Note: This story was updated to reflect that Buck White of The Whites is also one of the Opry’s oldest members at 92.