In 1938, he opened "Billy Rose's Diamond Horseshoe" nightclub in New York City in the basement of the Paramount Hotel off Times Square. It initially opened with a version of his Fort Worth show.

At the 1939 New York World's Fair, Billy Rose's Aquacade starred Olympian Eleanor Holm in what the fair program called "a brilliant girl show of spectacular size and content." He married Holm shortly thereafter, divorcing his first wife, comedian Fanny Brice. Future MGM star Esther Williams and future Tarzan Johnny Weissmuller were both Aquacade stars.

Following the Fair, Rose asked John Murray Anderson, who had staged the Aquacade, to recommend a choreographer for a new show at the Horseshoe. Anderson recommended Gene Kelly, then performing in William Saroyan's One for the Money. Rose objected that he wanted someone who could choreograph "tits and asses", not "soft-soap from a crazy Armenian." (Yudkoff, 2001).

But after seeing Kelly's performance, he gave Kelly the job, an important step in Kelly's career.

The Diamond Horseshoe operated under that name until 1951.