48th Street
In the shadowy world of Prohibition-era New York, Owney “The Killer” Madden reigned as a kingpin of nightlife, his fingers in more clubs than anyone could count. Fresh out of Sing Sing in 1923, Madden carved out a niche far above the city’s lower criminal circles, distancing himself from the likes of the Whittemore gang. Yet, his influence was undeniable. His friend and occasional partner, Bill Duff, who also had a storied past, ran the Silver Slipper, a speakeasy on Forty-Eighth Street that quickly became a hotspot—until it was padlocked just ten days after opening. Rumor had it that Duffy’s downfall wasn’t just the illegal liquor but that he’d stepped on the toes of local bootleggers by sourcing his hootch from out-of-towners. But in true Prohibition spirit, peace was brokered, and the Silver Slipper reopened, this time with the tacit blessing of the city’s underworld. The Three Sawdust Bums, including the iconic Jimmy Durante, found themselves back on its stage, entertaining a crowd that was as glittering as it was dangerous, in a city where the lines between law and crime were as blurred as the gin in the cocktails.