Like many popular nightspots of the day, Leon and Eddie's began as a speakeasy. In its case it started in 1928, in the basement of a converted house at 18 West 52nd (for a $700 investment) and could take as many as 30 customers at a time.
They later moved across the street to 33 W. 52nd after the end of Prohibition in 1933. Their new quarters had a retractable roof, rising stage and room for 475 customers. This retractable roof allowed air flow in a time before air conditioning was common. Like many places that became sweltering hot in the summer, they advertised a "Summer Garden" with open air flow from the roof that made dancing a possibility without everyone fainting from heat exhaustion. It was this Summer Garden that offered a pre-tiki atmosphere complete with (fake) swaying coconut palms. Advertising materials also featured dancing girls made up like hula dancers -- offering the exotic veneer to their otherwise normal bump and grind burlesque.
One of the most famous burlesque performers to perform there was Sherry Britton, who performed regularly for at least 7 years.
Leon & Eddie's was one of the more reputable spots on this block known for hot jazz, strippers and mob-run clip joints. Unlike its fabled neighbor '21', Leon and Eddies did not cultivate celebrities and socialites through a policy of exclusivity. This was a rowdy joint patronized by local businessmen and out-of-towners who enjoyed the bawdy humor, singalongs, vaudeville-like revue and strippers the club featured. It was very well-known, being frequently mentioned in the press or in magazines.
The sign out front of the club said "Leon and Eddie" without the apostrophe s. Another sign at the door was a takeoff on the famous Earl Carroll slogan and read "Through these portals, the most beautiful girls in the world pass out!" A sign posted over the swinging kitchen doors stated “Through these portals pass the most beautiful waiters in the world!" The walls were covered with tongue-in-cheek murals. On either end of the back wall, Leon Enkin and Eddie Davis thumbed their noses at each other in caricature. The gravel-voiced Davis was the face of the place and frequently performed his repertoire of risque songs.
The club did not last long into the postwar period. Leon and Eddie dissolved their partnership in 1947. Charlie Davis kept it going until his retirement in 1953 when Toots Shor, who had been day manager, and some say part-time bouncer, at Leon and Eddie's in its early years, opened a restaurant at the site.