Walk into Herman Roberts’s south-side home, built for his mother in 1965, and the first thing you see are the photographs lining the walls of his living room. He has dozens if not hundreds, including pictures of musicians James Brown, Sarah Vaughan, Jackie Wilson, Dinah Washington, Bill Doggett, and Billy Eckstine; athletes Joe Louis and Muhammad Ali; political and civil-rights leaders Martin Luther King Jr., Harold Washington, and Jimmy Carter; comedians Dick Gregory, Slappy White, Nipsey Russell, and Stepin Fetchit; and author James Baldwin. They’re souvenirs of the years he spent running some of the best-known nightclubs on the south side of Chicago.

Born in Beggs, Oklahoma, in 1924, Herman Roberts migrated with his family to Chicago when he was 12. “Left my dog and my horses,” he says. He remembers going barefoot in yards speckled with chicken shit. “Getting ready to go to bed at night, you take your feet and rub it in the sand and dirt. We didn’t have any water to wash our feet off with.” In Chicago he had a better chance of finding paying jobs. “Selling papers, shining shoes, cleaning up kitchens, doing a little work putting coal in furnaces,” he says. “You probably don’t remember that. Now you’ve got gas and electric heat all the time. Ain’t no furnaces with stokers no more.”

Between 1957 and ’61, Roberts booked the likes of Nat “King” Cole, Sammy Davis Jr., Count Basie, and Lionel Hampton, plus lots of R&B acts he felt had adult appeal: the Treniers, Brook Benton, Sam Cooke, Jackie Wilson. Roberts has a special affection for Wilson: “Sheeit, he could put Sam Cooke to shame! Don’t bring Jackie Wilson on first and then bring out Sam Cooke behind him! It ain’t gonna work!”

Perhaps the biggest milestone for Roberts’s businesses was the passage of the Civil Rights Act of 1964, which forbid discrimination based on race, color, sex, or religion. Though this law gave blacks the legal right (if not necessarily the actual freedom) to go wherever they pleased, Roberts admits, “It hurt me.”

“Green what?”

“They wouldn’t cross the street for $500 now. Take, like, Prince. He can get a million dollars any night he wants to work. Millions! Right now, if Prince comes to town, somebody will be paying $200, $300 dollars to go see him. I might not want to pay it, but somebody’s gonna pay it.” That’s not to say he wouldn’t find the money to see Beyonce: “Shit, man, she’s got the finest body on her that anybody’s ever seen! I’d give $1,000 just to rub her butt! Ooh wee!”