Although the Osbornes were born in Roark, Kentucky, on Jack's Creek, they moved to Hyden, Ky., after their house burned down. Then, they grew up near Dayton, Ohio and had their first experiences as entertainers in southwestern Ohio. In 1952, Bobby was drafted into the military, and Sonny went to work with the "Father of Bluegrass Music" Bill Monroe. Upon Bobby's return from service in 1953, the Osbornes teamed up with Jimmy Martin, performing at radio stations WROL inKnoxville, Tennessee and WJR in Detroit, Michigan. At their only session together, on November 16, 1954 the Osbornes and Martin recorded six songs for RCA Victor. In late 1955, the Osbornes left Martin and moved to Wheeling, West Virginia, where they performed on WWVA Jamboree until Christmas, together with Charlie Bailey. They returned to Dayton in early 1956 playing the local clubs with guitarist Enos Johnson. When Johnson left, the Osbornes added guitarist Red Allen and fiddler Art Stamper to form a new group.
The Osborne Brothers and Red Allen (under the pseudonym Stanley Alpine) recorded for Gateway Records in February or March 1956 cutting eight instrumentals. In the spring of 1956, Tommy Sutton, a local disc jockey, helped the Osborne Brothers get a recording contract with MGM Records. The new group, with the Osbornes on banjo and mandolin, Allen on guitar, Ernie Newton on bass, Tommy Jackson and Art Stamper on fiddles, made their MGM recording debut on July 1, 1956. Their first released 45 RPM single for MGM containing "Ruby Are You Mad" became a huge success and led to the Osbornes being signed on as regular members of the WWVA Jamboree in October 1956. The "Jamboree version" of the group comprised Ricky Russell on dobro, Johnny Dacus on fiddle and Ray Anderson on bass. "Ruby Are You Mad" marks the first time twin banjos were used on a bluegrass recording. On October 17, 1957, at their third session for MGM, the Osbornes, always experimenting with their sound, added a dobro and drums, also for the first time on a bluegrass recording. In April 1958, Red Allen, who was the last musician to receive billing next to the Osborne Brothers, left the group.
Upon their breakout into the bluegrass scene, the Osborne Brothers quickly became noted for their virtuosic instrumentation and tight, melodic vocal harmonies. Their first country chart appearance in 1958 was "Once More", as a trio with Red Allen. The song featured a then-novel inverted stacked harmony: Bobby singing the lead line highest, then Sonny singing baritone, and finally the third singer (in this case Red Allen) singing the tenor as the lowest part. This placed Bobby's distinctive voice as the lead, and made the third voice a somewhat interchangeable part. As a result, the brothers could hire a series of guitarist/singers without changing their overall sound. This "high lead" vocal trio became their signature sound, used to great effect in the country market, with songs like "Blame Me", "Sweethearts Again", and a remake of the Carter Family's "Fair and Tender Ladies".
During the 1960s the brothers caused some controversy among Bluegrass music purists for their incorporation of electronic and percussion instruments in their live acts and studio works. In 1960 they became the first bluegrass group to perform on a college campus, at Antioch College. In 1963 they signed withDecca Records. On August 8, 1964 the Osborne Brothers were inducted as members of the Grand Ole Opry.
The Osborne Brothers recorded their tremendous hit "Rocky Top" in November 1967. Released on December 25, 1967, it sold 85,000 copies within two weeks. In 1973 the Osborne Brothers became the first bluegrass group to perform at the White House.
The Osborne Brothers have the distinction of having recorded two songs that would go on to be officially voted as "state songs." The first, "Rocky Top," was named a Tennessee state song in 1982. The other, "Kentucky," was named a state song for the brothers' home state of Kentucky.
Their song "Ruby Are You Mad" came in 1956 after signing with MGM Records (1956) and began a string of hits through 1986. Among them were "Once More" (1958), "Up This Hill & Down" (1965), "Making Plans" (1965), "Rocky Top" (1967), "Tennessee Hound Dog" (1969), and "Midnight Flyer" (1972). The Osborne Brothers' final chart appearance came in late 1986 with a new version of "Rocky Top".
Sonny retired in 2005, but Bobby continues to perform with his band Rocky Top X-press, which includes two of his three sons. They performed May 31, 2013 at the rededication marking new ownership of The Gatlinburg Inn, where Boudleaux and Felice Bryant wrote "Rocky Top," and the couple's sons, Dane and Del Bryant, were on hand.