Radin was the son of Broadway promoter Al Radin, who owned a speakeasy and promoted Broadway shows in the 1920s and 1930s. Roy Radin was a high-school dropout who joined the Clyde Beatty Circus at the age of 16 doing publicity work. A year later, Radin signed George Jessel and J. Fred Muggs as part of his first traveling show. Radin continued to put together vaudeville shows and became a millionaire before the age of 20. Shows were packaged with Roy Radin's name getting first billing (e.g., The Roy Radin Vaudeville Revue, The Roy Radin Variety Show, Roy Radin's Vaudeville '77). The shows featured comedy acts including George Gobel, Frank Gorshin, Jack Carter, Jackie Vernon, Milton Berle, Jessel, and The Roy Radin Orchestra. Berle and Jessel were among the regular masters of ceremonies. Comedians had a love-hate relationship with the tours, with Radin routinely becoming the butt of jokes. Reflecting on one tour, George Gobel told Johnny Carson on The Tonight Show, "Roy Radin knows as much about show Business as a pig knows about church on Sunday."