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.

Many of the folks in those photos performed at Roberts Show Lounge, which he founded in 1954 and closed in '61, or at the 500 Room, a hall in the sixth and largest of his Roberts Motels (in ads he called it "the Big One"), opened in 1969 and shuttered in '92. Not much architectural evidence of his entertainment empire survives: Roberts Show Lounge stood at 6622 South Park Way (since renamed King Drive), on a lot now occupied by New Beginnings Church. The 500 Room and its associated motel were a few blocks away at 301 E. 63rd, where there isn't much of anything today. But Roberts still has his story, and this is the first time he's shared so much of it publicly.

Roberts, now 90 years old, is a survivor of an era when racial segregation operated with much more explicit official sanction than it does today, and penetrated even further into daily life. Even the most crossover-minded black superstar might be required to play in a venue where blacks weren't allowed or, at best, were forced to sit in the rear of the club. (The last Jim Crow laws in the States weren't overturned until 1965.) Roberts provided a nonsegregated venue for black entertainers, with a classy ambience—and beginning in 1960, when he opened the first of his six motels nearby, he also gave them a place to stay. First-class hotels often refused black guests, and previously Roberts often had to put up his performers in houses or apartments.

Roberts's friend Marcella Saffo, who's known him since 1947 and married his old army buddy Walter Pride (now deceased), still remembers how much fun she had at Roberts Show Lounge. "You knew everybody, everybody knew you—they had Della Reese and all types of different stars there. It was friendly, you could talk to them. It was clean, it was managed well, there was never any commotion. Everybody was always having a nice time." And venerable blues songwriter Bob Jones recalls the glow of prestige that used to surround the place: "I lived in the suburbs, Chicago Heights. At that time, Roberts Show Lounge was the thing! I remember I was dating a young lady who decided she wanted to make a grand entrance, so she walked through the front door dragging her fur coat on the floor. Everybody thought that was funny."

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."

In Chicago, he entered the workforce in the late 30s, working for a cab company washing cars. "The reason I got involved in the cab business is because I was a young kid hanging around the cab garage," he says. "Back then, it cost 50 cents to wash your car. They'd give me a dime to wipe it off." He began driving those cabs at 15, as soon as he was old enough, and by 1944 he owned his own operation, the Roberts Cab Company. He served in the army during World War II, and after his return, in 1947, he claims to have been the first to install two-way radios in his cabs ("You gotta stay with the times!").

In 1952 Roberts established a small club called the Lucky Spot at 602 E. 71st. Two years later he moved to 6622 South Park Way, where he established Roberts Show Lounge. (The front of the building said "Roberts Lounge and Liquors," and in the late 50s he added a big neon sign reading "Roberts Show Club," but people who remember the place today tend to call it Roberts Show Lounge.) Jazz musician Duke Groner, another Oklahoma native who'd moved to Chicago, appeared on opening night. According to Saffo, "Roberts Show Lounge was a garage where Roberts Cabs used to be. We cleaned that out one time to have a big western birthday party for Herman. We cleaned that place up and had bales of hay around, all that sort of thing. This is how he got the idea of a club, because we had so much fun."

Roberts suggests other reasons he got into the business. Pointing at a picture on the wall of his 35-year-old self surrounded by eight women, all of whom worked at his club, he says, "See the girls up there? That's the reason I established a nightclub. I'd rather go to dinner and have a conversation with a girl than a man!" At the time, women were still a relative rarity in the workplace. By his own reckoning, Roberts helped break down barriers—and he's pretty sure more men came to his club as a result. "Some people can walk over something and don't know whether it's good or not," he says. "I was able to see off the end of my nose."

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At the time, the south side wasn't hurting for entertainment; the Regal Theater was still going strong on South Park close to 47th Street, and the area around 63rd and Cottage Grove was a nightlife hotbed. But in Roberts's view, the neighborhood scene was lacking in national acts. "They had a good cabaret show—band, chorus line—but no names." So in 1957 Roberts expanded his venue and renamed it Roberts Show Club, reasoning that a bigger hall would attract bigger artists. The night it reopened, the revamped club presented jump-blues pioneer Louis Jordan, who'd foreshadowed rock 'n' roll with a string of hits for the Decca label between 1942 and '51, including "Saturday Night Fish Fry" and "Choo Choo Ch'Boogie." By the time he made it to Roberts, Jordan hadn't had a big single in a while, but he was still an impressive draw.

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!"

Roberts tended to stay away from blues acts. "I wouldn't even play B.B. King. That's west-side shit! Forty-third Street bucket-of-blood stuff!" he exclaims. "We wanted to stay away from that. We just left it, right? Now you wanna go back to it." He was also hesitant to book younger jazz artists, leaving that to the London House downtown, though the accessible sounds of Ramsey Lewis played well. Roberts focused on black acts, but he'd make exceptions for big draws such as Tony Bennett and Gene Krupa. And the club's biggest white crowds came out to see the Jewel Box Revue, a troupe of two dozen drag queens. They'd arrive at the club in their street clothes, then transform themselves before showtime, wearing an array of elaborate dresses. "They're women, then," says Roberts. "You'd treat 'em like women. And some of them looked better than women, when they got through makin' up!"

Some of Roberts's favorite stories involve famed jazz diva Dinah Washington. "Nobody could beat Dinah Washington singing. She was always in the driver's seat," he says. "I paid her to do the show, right? I got all these people coming to see her. I'm not nuts. I wasn't gonna lose money. If she don't show up, I gotta give these people their money back. Why would I want to start a fight? I could kiss her ass long enough for her to finish. I can get along with anybody—except I ain't going to bed with you. She didn't beat me across the head—all she said were some words. There may not be anything wrong with what's going on, but she might make something wrong. I could be walking across the floor and she'd say, Herman Roberts? Have my money ready when I come off the stage! Why would she be hollerin'? I'm gonna pay her anyway. She knows that!" Washington also started wearing wigs before it was fashionable. As Roberts recalls, if a woman stared too hard at her hairpiece, Washington would snarl, "Bitch, you better try to get you one!"

Even though Roberts became nearly as famous locally as the people he booked, he didn't delude himself that he was friends with his stars. "It's only for a short time. Anybody important, you won't get to be friends with them but so long," he says. "They're busy and I'm busy. We ain't got no time to hang together, man. 'Hey, how you doin', Joe, I'm on my way to so-and-so—let's go and have a bite to eat or something.' You'll be lucky to do that!"

Roberts doesn't have much to say about why the club closed in 1961. "Everything goes through changes, man! How come the Chicago Defender and Ebony magazine aren't as strong as they used to be?" The building became a bowling alley, which lasted roughly 30 years. The Roberts Motel chain likewise kept going into the early 90s, and the largest of those establishments, opened in 1969 at 301 E. 63rd, continued to book music occasionally—most notably in the 500 Room, named for its capacity. Ramsey Lewis played opening night, and other big names included Bobby Bland, Billy Eckstine, and jazz-blues chanteuse Esther Phillips. A photo of an Eckstine show from this period shows him performing outdoors on a terrace to a packed crowd, with many people watching from a hotel balcony.

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."

When the Roberts Motel on East 63rd was the classiest on the south side, it was the biggest fish in a relatively small pond. Just about every famous African-­American who came through Chicago stayed there, even if he or she was performing up north. After 1964, though, it faced stiff competition from hotels downtown. His older clientele sometimes came back around, but it wasn't enough. "They could go downtown to the Hyatt or the Sherman House—they ain't in no black hotel! [You could now] go to Las Vegas; you think I'm going to look for where the black faces stay? [Before, if you] go to Las Vegas, you had to go where the black faces stay. You couldn't stay on the strip!" In Chicago, he says, blacks couldn't go to the Tivoli Theatre. "See how a matchbox looks? We didn't get out of that matchbox!" he says. "I had it all in my hand. You couldn't stay nowhere but my places. When they opened up the doors downtown, I lost a lot of business—all the top-money people. Smokey Robinson and all those people, they're checking in downtown at the Hyatt."

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The south-side club scene thrived for a couple more decades, but Roberts doesn't think it was ever the same—he describes famed 60s and 70s showplaces such as the Burning Spear and the High Chaparral as "low-key." Clubgoers could still see big R&B names of the day such as Little Milton and Tyrone Davis, but Roberts came from a time when a concert wasn't just a concert, it was a variety show—much like what his idol Ed Sullivan did on TV. Comedians and chorus girls shared the spotlight with honkers, pickers, and shouters. Even now, Roberts considers his old club the last of a breed.

"You can't find one nightclub in Chicago. Not one! Name me one nightclub in Chicago!" he says.

The Green Mill?

"Green what?"

You know, the reputed Al Capone hangout that's been open for literally 107 years in Uptown?

"It ain't no big nightclub, man! Got a little band in there playing, somebody that's making some noise. That ain't no nightclub! That ain't no chorus line, no great big show like Chez Paree."

Roberts acknowledges that "they got a little something over there in Hyde Park that opened up" (meaning the Promontory at 53rd and Lake Park), but he defines a "nightclub" as a place with an "emcee, chorus line, a full cabaret show." And he's right, that's something that barely exists these days. "A lot of people haven't even seen a cabaret show," he says. "Right now, I'll tell you, if I was younger, I'd go build me a club over on 47th Street—all the people I knew, [plus] some of those people that's making millions of dollars now, like Taylor Swift and all those girls."

If the younger Roberts were opening a club today, he'd likely need better cash flow. "Everybody's pricing themselves out of the business now," he says. "Right now, you can't buy nobody unless you're paying $10,000, $20,000, $50,000 a night. Back then, you could buy anybody you want for less than $5,000. I paid Count Basie, Joe Williams—the whole band for a whole week—less than $5,000. Like Dick Gregory and all them, I paid them $35, $40 a night! Nipsey Russell flew from New York City to Chicago and back—a round-trip ticket and everything—for $500.

"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!"

The rise of disco didn't affect Roberts's business at the 500 Room the way it hurt other club owners. He eventually quit booking anything himself, and like the Regal and East of the Ryan today, his hall became a rental space, where anybody with enough money could bring in whatever he or she wanted. "When I got to be a certain age," he says, "I started to get rid of everything I had."

Roberts retired in 1992, when he was in his late 60s. Though he still lives on the south side, he also keeps a ranch in Oklahoma. He remains justifiably proud of his accomplishments, but he knows he didn't walk alone. "One person can help change things, but they won't change it overnight," he says. "Even Martin Luther King. He could have had some help, but there's no way he could change everything. Personally, being a leader, you're supposed to try to get people to follow. But sometimes they get a bad name trying to get people to follow, because they're stepping out of their boundaries." Roberts didn't step out of bounds so much as draw a new, better boundary line for Chicago's African-­American nightlife.