He never played Bluegrass, and was well-known for his Western-style music. Fans describe his voice as extremely similar to that of Tex Ritter, the 1930s and 1940s singing cowboy. According to a 1990 interview with Osborne, Ritter came to WCYB radio station, the station both the Stanley Brothers and George Osborne played on, in the mid-1950s, and was so impressed by George's rendition of his song, "Ballad of the Boll Weevil" that he visited George's house and ate dinner with him and his mother.
With the 1966 death of Carter Stanley, George broke out on his own, performing locally in the hills of Southwest Virginia and Northeast Tennessee. In 1984, he began playing with his half-brothers, Uncle Charlie Osborne and Emmett Osborne, continuing to do so on a semi-regular basis until Emmett's 1990 death and Charlie's 1992 death. George mostly retired in 1992 to a quiet life in Bristol with his wife, Eula, although he occasionally gave performances locally and later at the Birthplace of Country Music Museum in Bristol, Virginia.
George relished his position as a Dean of the Mountain Music society in the Blue Ridge Mountains, having mostly changed his style after Tex Ritter's 1974 death.
George owned 40 acres (162,000 m²) of riverfront property in rural Mendota, Virginia, which is still owned by his wife.
In August 1998, George was to make a phone call to a family member. When he didn't call, family became worried, calling the police to his home. He was found dead of natural causes in his small home in Bristol, Tennessee.