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."
Radin expanded his shows to concentrate not only on comedy revues but also musical acts largely consisting of fading 1950s and 1960s performers. The performances were often in poorly equipped high school auditoriums and gymnasiums requiring lengthy bus rides. Musical performers included The Drifters, Eddie Fisher, The Serendipity Singers, The Shirelles, and Danny and the Juniors.
Throughout the 1970s, Radin's company Roy Radin Enterprises had multiple shows running at the same time. The tours were creatively financed, always showing as sold out but sometimes sparsely attended. Tickets were often sold as benefits for handicapped children, police officers, fire fighters or local causes. Advertisements by local communities were purchased in the souvenir magazine distributed at the venue. The financing was investigated by New York state Attorney General Louis Lefkowitz in 1975 after he found that only 27% of the funds were going to one of the attributed charities.
In April 1980, Actress Melonie Haller claimed that she had been beaten and raped during a party hosted by Radin at his Southampton, New York home, and that the events had been filmed. Radin countered that Haller had willingly taken part in sadomasochistic sex games. He was charged with menacing Haller, Criminal possession of LSD and cocaine, and illegal possession of a handgun. Radin pleaded guilty to the weapon possession and the other charges were dropped. He was fined $1,000 and given three years probation on the weapons charge. Businessman Robert McKeage IV, also in attendance at the party, plead guilty to assaulting Haller and was sentenced to 30 days in jail.
As The Cotton Club film financing was being arranged, the 33-year-old Radin was murdered. He vanished en route to a scheduled Beverly Hills conference on May 13, 1983, and was reported missing days later by his personal assistant. His remains were found a few weeks later by a forest ranger near Gorman, California, about 65 miles (104km) north of Los Angeles.