Jimmy Randolph started to become known, singing in night clubs throughout the city. His strong voice did not go unnoticed. On January 1956 he signed with Mercury Records. Jimmy Randolph also did appearances in the famous Cotton Club in the late 50s. At that time, he also sang for the Duke Ellington and his orchestra along with Barbara McNair at the Copa City in Miami Beach. Then he continued to do appearances in various clubs and hotels as well as to releasing 45". In 1966 he did first appearance on TV (Porgy in Wien). He played along with Robert Guillaume. He made a five-month tour throughout France in the late 60s. He tried to promote his songs through this trip in France. In 1971 he received one of the highest honors to noncitizens by Liberian Government, because he composed a special song, titled "Liberian". He continued to sing in various clubs and hotels such as "Riviera" in Las Vegas 1972 and "Stardust" with Lionel Hampton in 1974. He also did appearances in a few TV series. In 1976 is the big moment of Jimmy Randolph's career, using the name James Randolph. He participated at the Broadway Theatre in a Broadway revival of "Guys and Dolls" with an all black-cast as Sky Masterson along with Robert Guillaume as Nathan Detroit, Norma Donaldson as Miss Adelaide, Ernestine Jackson as Sarah Brown."Guys and Dolls" is a musical and was directed and choreographed by Billy Wilson. The show closed on February 13, 1977 after 239 performances and 12 previews.