Kelly started his career in his native Kentucky working for promoter Willie Davis. Also wrestled a bit in Indiana. In the early 60s he went to the North Bay territory and was mainly used as a referee. He became close friends with Terry & Ronnie Garvin who helped him get booked in the Gulf Coast territory in 1965. Within two years he went from referee to top babyface to booker (Mobile-Mississippi side). He stayed with the promotion until September of 1975 when he moved back to Kentucky. He worked for Bruiser & Gulas for about 7 months, the returned to the Gulf Coast until his retirement in December of 1976.
He was first given the name "Irish" Bob Kelly at the beginning of his career, but became "Cowboy" when he came to the GC. He had actually been a rodeo rider in the early 60s just after he was honorably discharged from the USMC.
His biggest name opponents were an assortment of Daltons & Fargos. His feud with Jack Dalton/Don Fargo lasted for ten years. He never faced any nationally known names when they came into the area. As booker, he always booked them against others in the area that he felt they would draw better with.