Before age eight, he had already gained a reputation in local show business circles by performing as a "boy magician" in Baltimore area churches.
As he grew into his teen years, he started to gain employment in local concert halls as a magician before breaking into the vaudeville circuit, where he made nine dollars a week.
Early in his vaudeville career, Green began to branch out from magic and work in burlesque acts.
His first major role was in the Broadway production of Hot Chocolates, a black musical review where he performed with the likes of James Baskett and Louis "Satchmo" Armstrong.
[5] However, Green did not gain his highest acclaim until he began to work with Amos 'n' Andy and Duffy's Tavern, the latter of which also became a hit movie.