Ray’s career began a definite decline in the early 1950’s. Increasingly, as he faced problems controlling his on-stage behavior due to alcohol, the venues open for Ray to work in became more limited. He began performing in smaller towns and in tourist clubs in cities like Miami that presented female impersonators to an exclusively heterosexual audience.
Ray recorded a series of LP’s on his UTC (“Under the Counter”) label during this period, providing the most comprehensive glimpse at his work. In ten albums of studio recordings, Ray would tackle songs and extended routines in the longer running times allowed by the then-new LP record technology. Some were gay-themed pieces, such as “The Wedding”, which concerned a police raid on a 1920’s Gay wedding in a Chicago church. Others poked fun at straight married life; in a series of routines called “The Family”, Ray plays a harried wife trying to keep her spouse and kids on the straight and narrow, so to speak, on a Sunday drive or a trip to a cafeteria. Available through mail order, “discriminating” record dealers, and Ray’s live shows, the albums proved popular and were still in print well into the 1970s.
Perhaps the most well known of the UTC records was Take a Look at My Operation, a collection of drag and gender-bending routines that promoted Ray’s apparent sex change procedure. The first successful gender reassignment surgery to gain widespread public attention had been performed on Christine Jorgensen a few months earlier. Ray told the New York Journal American and Variety in May 1956 that he had undergone the operation in Mexico and that it was “performed by Dr. Emrick Szekely, former Hungarian specialist now residing in Juarez”. He told the papers that “Dr. Szekely” had even found ovarian tissues during the procedure.
Researchers have assumed that the so-called “sex change” operation was likely a hoax on Ray’s part, but there may be some grain of truth to the story. An interview with Ray by FBI agents during an early 1960s espionage investigation noted that, “Bourbon laughingly stated his reason for having the operation was different than was Christine’s, in that he had wanted to save his own life.” Ray told the agents that he had the operation due to cancer, but, again, this may have been an instance of Ray re-writing his own history.
After the operation, Ray consistently billed himself as “Rae Bourbon” for his nightclub appearances, a stage name he had used on and off since the 1920s. Some people who knew Ray during and after this period recalled that, at least anatomically, he was still a functioning male. This more serious operation for cancer, combined with publicity for Christine Jorgensen, may have been the inspiration for Ray’s claim of a sex change and the subsequent integration of an operation into his comedy material. Ray told friends and other performers at various points that the reason for the sex change operation was to skirt local laws banning cross-dressing, making it easier for him to appear on stage. Interestingly, Ray quips during a rare 1954 live recording produced a few months before the sex change story that he plans to go to Denmark to “have more put on”.
The sex change hoax and Ray’s efforts to capitalize on the story did not help his career. Promoters had difficulty figuring out how to bill his act – when he opened at Jack Gordon’s Melody Room in West Hollywood in 1956, the club ran advertisements billing him as “Miss Rae Bourbon” and, in bold letters, a disclaimer that read, “NOT A FEMALE IMPERSONATOR”. Ray played to a sold-out audience that included three deputy sheriffs. Ray was hauled to jail in an evening dress and tiara, charged with impersonating a female. (The cover for Ray’s Hollywood Expose album included photographs of the arrest and booking.) While waiting for a jury trial, Ray returned to the Melody Room appearing in men’s clothing. However, representatives from the Los Angeles County Welfare Commission objected to the content of Ray’s “obscene and profane” routines. Eventually, after much press about the story and threats of withdrawal of the Melody Room’s license, the Commission banned Ray from Los Angeles nightclubs.
Thumbing his nose at the Commission, Ray opened his own revue, She Lost It in Juarez (?), at the Ivar Theatre in Hollywood. Since the show was staged at a legitimate theatre, the Commission had no jurisdiction. However, in November, the jury found Ray guilty of cross-dressing during his engagement at the Melody Room and Ray skipped town, rather than face a thirty-day jail sentence. By the end of the decade, Ray, still promoting himself as a female, ran into more trouble with the law for lewd behavior and female impersonation in Seattle, El Paso, and New Orleans. In 1958, he was even arrested in Miami for impersonating a man.