In June 1949, Bobby made
his first radio broadcast appearance at WPFB in Middletown, Ohio. At his
father's insistance, Bobby sang "Ruby" for the first time, and 50 telegrams
were received by the station asking them to have Bobby sing it again. They did,
he did, and as they say, "The rest is history!" That song became a signature
for The Osborne Brothers throughout their career. The first recording by The
Osborne Brothers was "Ruby". They sang "Ruby" when they became members of the
Grand Ole Opry. They performed it for President Nixon in the East Room of the
White House. Nearly 50 years later, it is still one of their most requested
In 1949, 17 year Bobby, along with Larry Richardson, joined the very first
Lonesome Pine Fiddlers band that featured bluegrass music, following the band's
stint playing western swing. This band consisted of Bobby on guitar, Larry
Richardson on banjo, Ezra Cline on bass, and Ray Morgan on fiddle. They
recorded four sides for Cozy Records, owned by John Bava. "Pain in My Heart",
"Lonesome Sad and Blue", "Will I Meet Mother in Heaven", and "Don't Forget Me".
In 1950, Bobby and Jimmy Martin started a band that went by the name of Jimmy
Martin, Bob Osborne and the Sunny Mountain Boys. They worked at the famous WCYB
radio station in Bristol, where others such as Mac Wiseman, Lester Flatt &
Earl Scruggs, Jim and Jesse, and The Stanley Brothers also performed. Members
of this band were Bobby, Jimmy, Curly Ray Cline, Charlie Cline, and Little
Robert (Robert A. Van Winkle).
In his early performing years, Bobby played with such bands as The Miami Valley
Playboys, The Silver Saddle Boys, and Rex & Eleanor Parker.
Bobby also worked a few weeks for the Stanley Brothers, just prior to being
drafted into the Marine Corp.
1951-Bobby was drafted into the U.S. Marine Corps, and was stationed in Korea
during most of the fierce fighting. He was wounded in action and received the
Purple Heart medal.
Bobby's interests include:
Caring for his home and yard
Putting out a garden every year
Works on the tractor on his farm
Old Western movies
Keeping up with world news
SEC Basketball - Kentucky Wildcats fan
Big 10 Basketball
NBA Basketball - Chicago Bulls, Utah Jazz, Boston Celtics