Gangster Owney Madden bought the Cotton Club in 1923 from heavyweight boxer Jack Johnson, who had called the club Club De Lux. With money from Al Capone and other gangster friends Madden opened a place where the moonshine whiskey that they made could be served.

The club was decorated and designed to recreate the atmosphere of a stylish plantation. Almost without exception, the clientele were white and the entertainers were black. This "white only" policy enhanced the club's reputation at that time, and it became the place to be. Getting into the club wasn't easy, and only those with money, reputation, celebrity, or influence made it in the doors. Inside gangsters, celebrities, and the wealthy mingled while being entertained by some of the best. Many early black entertainers got their start in the Cotton Club, including Lena Horne, The Nicholas Brothers, Cab Calloway, Ethel Walters, and Duke Ellington. Among the celebrities that frequented the club were Bing Crosby, Doris Duke, Cole Porter, Dorothy Kilgallen, Irving Berlin and Jimmy Durante.

A specialty at the Club was the Cotton Club Revue. The first Cotton Club revue was in 1923. There were two new fast paced revues produced a year for at least 16 years. The earliest shows were staged by Lew Leslie, famous for his "Blackbird" series. The Duke Ellington Orchestra was the "house" orchestra for a number of years followed by Cab Calloway. The revues featured glamorous dancing girls, acclaimed tap dancers, vaudeville performers, and comics. All the white world came to Harlem to see the show.