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.