A Virtual Tour of New York's Real Speakeasies of the 1920s and '30s

The Cotton Club — 644 Lenox Avenue

Despite being home to the greatest black entertainers of the era, including Lena Horne, Count Basie, Ella Fitzgerald, Louis Armstrong, and Duke Ellington (who was the house band during Prohibition), Harlem’s Cotton Club was strictly whites-only — and also strictly upheld a standard of extreme racism. Its owner, bootlegging gangster Owney Madden, ran the club from Sing Sing as a place to unload his bootleg beer, attracting celebs and locals who wanted in on the best jazz performances in New York.