He later performed in comedy shows and theatrical productions in Seattle, Washington before relocating to Detroit, Michigan. In Detroit, Ray regularly performed at the Flame Showbar, an African-American nightclub, where he developed a local following. While performing at the Flame, Ray attracted the attention of Bernie Lang, a song plugger, who saw him perform with local DJ Robin Seymour of WKMH. Lang went to New York to sell the singer to Danny Kessler of the Okeh Records label. Kessler came over from New York, and he, Lang, and Seymour went to the Flame. According to Seymour, Kessler's reaction was, "Well, I don't know. This kid looks well on the stand, but he will never go on records."