Ray’s friends relate that his entry into show business occurred when he sent a photograph of himself dressed as “Rae Bourbon” to a Photoplay magazine contest. (In a 1931 newspaper interview, Ray mentioned the publication was Motion Picture Magazine, which did run annual contests to find new film personalities.). When he arrived in Hollywood to claim the top prize — a contract with Paramount — studio executives were, of course, surprised to learn that Ray was actually a man and somewhat perplexed about what to do with him.
Someone noticed a resemblance between Ray and Esthelle Taylor, a Paramount contract actress and one-time beau of prizefighter Jack Dempsey. So, Ray was hired as a stuntman and stand-in for her films. This “cross gender” casting was quite common in silent films; contract players would help out with small walk-on parts and stunt work as directors improvised on the set of these early movies in the days before unions. We have also found material in Scenario magazine from the early 1920s, showing that Ray was writing film screenplays under the name “Ramon Icarez”, and other trade publications showing him using that name for his work acting in films during this period. He even performed, under the name Ramon Icarez, a “fire dance” that was a hit at the opening ceremonies of the Los Angeles Coliseum.
Ray became part of a small circle of professional friends on the Paramount lot that included William Boyd (later famous as Hopalong Cassidy) and Rudolph Valentino. Ray has been spotted in a few silent films in bit parts and walks-ons. After a bullfight, he dies in the arms of Valentino in Blood and Sand (1922) in the opening scenes of the movie and appears in later reels as a bodyguard. In his memoirs and trial testimony, Ray notes that he appeared in Manslaughter (1922), a Cecil B. DeMille drama with Thomas Mims; The Volga Boatman (1926) starring William Boyd; Beyond the Rocks (1922) with Gloria Swanson; and Pola Negri’s first picture, Bella Donna (1923). Near the end of his life, Ray would quip that he was in Demille’s original production of The Ten Commandments – “Not with the original Moses although I may look that old.”
Ray apparently stayed active in his contacts with the Hollywood filmmaking community after the silent era. In his memoirs, Ray tells of his accompanist, Duke Kewish, recognizing him in a bit part in Golddiggers of 1937; indeed, Ray can be seen in a medium shot dancing with an attractive woman in a scene at the pool party about half-way through the movie in a non-speaking role on a train in the opening scene of the film. Ray told friends that he also appeared in a series of comedy shorts, calling them some of the “worst ever made”, but it appears they do not survive.
After his stint in silent films, Ray branched out into vaudeville, touring just as the rise of sound films were starting to erode the popularity of stage performers in many venues. Ray and fellow vaudevillian Bert Sherry formed a team and found steady work between 1922 and 1924 in vaudeville and burlesque houses in the U.S. and England. Sherry played the straight man to the more outrageous Ray, who would often work in drag. Although Ray doesn’t discuss his work or friendship with Sherry in his incomplete memoirs, Ray is known to have kept in touch with Sherry until at least the early 1960’s. (Sherry himself operated gay nightclubs in Baltimore for thirty years.). Ray continued touring on the vaudeville circuit, represented by the William Morris Agency, through the end of the 1920’s.