Herman Roberts founded the Roberts Show Lounge in 1954 and this venue in a former garage became a hub for Black entertainment in Chicago as well as a central part of this Oklahoma native’s entrepreneurial empire. This room—which had been a garage for Roberts’ taxicab company—brought to the neighborhood such popular stars as Louis Jordan and Count Basie as well as former Chicagoans Dinah Washington and Sam Cooke. The club also presented elaborate stage performances, including cross-dressing act, the Jewel Box Revue. While the city remained segregated, Roberts staged white performers like Tony Bennett as well as white audiences to the South Side. Roberts also operated six nearby motels, one of which on nearby 301 E. 63rd Street, included a small entertainment spot, the 500 Room. The Show Lounge closed its doors in 1961 and Roberts retired from business in 1992. He died in 2021 at the age of 97.

– A.C. 

Caption: Former location of Roberts Show Lounge.