In the late fifties and early sixties Herman Roberts provided entertainment on the Southside of Chicago when top entertainers were not available in all white establishments. He opened a small lounge called the lucky spot on 71stand South Park (King Drive) in 1953 but always knew he would build something bigger. After another year he moved further north to 66th, where he housed Robert’s taxicabs the first to have two-way radios installed. He later renovated that building into what became Roberts Show Club.
Roberts Show Club was not just a venue for Blacks only; he invited white performers and also had many of Chicago’s white social world come to his all-inclusive establishment. Hugh Hefner was a frequent visitor, along with Irv Kupcinet of the Chicago Sun-Times. It was at Roberts show Club that Hugh Hefner saw Dick Gregory and brought him into his Playboy Club circuit. Entertainers such as Sammy Davis, Dinah Washington, Billy Eckstine, Count Basie, and George Kirby could be seen nightly on the marquee that graced the multi granite building at 6630 on what was then South Park.
Roberts Show Club was making changes, but not in where his performers could stay; thus came his idea for building Roberts Motel at 6625 South Park (King Drive); right across the street from Roberts Show Club. After having overwhelming success with that motel he built two more at 38th and Michigan, a fourth at 79th and Vincennes and another at 65th and South Park (King Drive). His pride and joy, The “500 Room” a motel that housed 250 guest rooms, three penthouse party suites, the 300 room bar and lounge, travel agency, restaurant and beauty shop, was opened in 1970. It remained “The” place for his Black community to have events that they still were being denied to have in some white establishments downtown. The chandeliered ballroom and winding staircase gave many opportunities for pride filled parties and many events. Mayors Daley, Bilandic, Washington and Sawyer, Governors Walker, and Ogilvie were just some of the political figures who walked those stairs along with other political dignitaries.
His energy was later given to other ventures and he closed his show club and through the persuasion of several friends who bowled, he renovated that taxicab, show club building again. Roberts Bowl opened and provided recreational family activity until 1990. Still wanting to keep a community-based business he changed Roberts Bowl into Route 66 Roller Rink; using the road name that he and his family traveled on their way to Chicago. Along with his Chicago interests, he opened a motel in Gary, Indiana and Oklahoma. He was an African American honored by many organizations as a man with vision, but the one he cherished greatly was recently when a portion of King Drive was named “Herman Roberts Way.”
The man from Oklahoma who made Chicago his home and the place he wanted to make his dream happen died in Las Vegas surrounded by his wife Sonja and children on Sunday, January 31, 2021. Herman was 97 and loved the neighborhood in Chicago that surrounded his beginnings.
Because of the pandemic, his interment will be in Las Vegas, but he will be honored with another celebration in Chicago at a later date.