Herman Roberts, who brought stars to Chicago (and also could work a ranch), dead at 97

Herman Roberts surrounded with some of the photos from his career as a nightclub, taxi and motel entrepreneur. | Alison Green/Chicago Reader

Herman Roberts came to Chicago with nothing during the Great Migration and wound up a tycoon.

At one time or another, he owned 35 taxis, eight motels, a nightclub that swung with some of the world’s greatest stars, a bowling alley, a skating rink and oil wells on a 2,000-acre ranch in Oklahoma.

Mr. Roberts, 97, was buried last month at Southern Nevada Veterans Memorial Cemetery. He died at home in Las Vegas, where he’d moved to be near family and enjoy warm weather.

He liked visiting Caesars Palace hotel. When he was out on the Las Vegas Strip, his granddaughter Hermia Roberts said, it wasn’t unusual for transplanted Chicagoans to recognize him, saying: “Oh, my God, Herman Roberts is out here in Vegas!”

He’d say, “I don’t know how to sing, dance, act, tell jokes.”

“But he knew how to put everything together,” his granddaughter said.

Herman Roberts.

In the early 1950s, he opened his first lounge, the Lucky Spot, at 71st Street and what’s now Dr. Martin Luther King Jr. Drive.

A few years later, he opened the Roberts Show Club in a garage that once held his cabs. The South Side club featured stars including Sammy Davis Jr., Nina Simone, Sarah Vaughan, Dinah Washington and Jackie Wilson.

Mr. Roberts liked Wilson’s panache.

“He could put Sam Cooke to shame!” he once told the Chicago Reader. “Don’t bring Jackie Wilson on first and then bring out Sam Cooke behind him! It ain’t gonna work!”

Among the comics who worked the crowds there were Redd Foxx, George Kirby and Moms Mabley. Hugh Hefner dropped in. After seeing Dick Gregory perform, he hired him to perform at his Playboy Clubs.

Photos from the heyday of Herman Roberts’ Show Club, also called the Roberts Show Lounge.

Knowing that Black entertainers and customers weren’t welcome at most downtown hotels, Mr. Roberts in 1960 built the first Roberts Motel across the street from the Roberts Show Club. He expanded to six more South Side motels and one in Gary.

The showpiece was his sixth motel, at 301 E. 63rd St. It had a plush ballroom dubbed the 500 Room.

“It had a winding staircase and a chandelier that came from almost the roof to the staircase and a terrazzo floor,” said Sonja Roberts., his widow.

Mr. Roberts wired the 63rd Street hotel so patrons could watch Muhammad Ali fights from their rooms, the bar, the banquet rooms or even outdoors.

Around 1974, he installed a removable stage in the parking lot and mounted shows featuring Count Basie, Billy Eckstine, Ramsey Lewis, Della Reese and comic Nipsey Russell. They were beautiful evenings under the stars, his wife said.

Over the years, the original show club evolved into a skating rink and bowling alley, his wife said.

“Everybody talks about the motels, but Herman had another side,” his wife said. “Herman was really an outdoorsman.”

He liked working on his Oklahoma ranch. It was on family land Mr. Roberts was able to re-buy after it was swindled away from a relative around the time of the Great Depression, according to his wife.

At its peak, Mr. Roberts’ ranch had several oil wells, 100 horses, pigs, the gentle French breed of cattle called Charolais and even peacocks.

He grew up one of six children in Beggs, Oklahoma. Around 12, he arrived in Chicago with his family. He went to Burke grade school and washed cabs for change. After Englewood High School, he built a taxi fleet that crisscrossed the South Side at a time when white-owned cabs usually wouldn’t.

Mr. Roberts and his first wife Gladys had three children. They divorced around 1959, Sonja Roberts said.

She was his receptionist but said she had no interest in her wisecracking, hard-charging boss.

Herman Roberts at his ranch in Oklahoma.

But she saw him in a different light when she and a secretary visited him at the ranch.

“He could use the backhoe, use the tractor, he could put a fence up, shingle his roof,” she said. “He loved to be riding his horses. He could reach in a cow and help birth a calf.”

At one point, “Herman rode up to us on his horse,” she said, “and I jumped over the fence and rode on the back of the horse and rode away with him. It’s been shaky, but I rode with him for 56 years.”

They were married in 1965 and had three children.

Besides six children from his two marriages, he acknowledged 11 more, his wife said. Three sons died before he did. Mr. Roberts is also survived by 27 grandchildren and five great-grandchildren.

He loved Patti Labelle’s sweet potato pies. And every Sunday he used to enjoy watching Frazier Thomas’ WGN movie show “Family Classics.” His favorite film was the heart-tugger “Our Vines Have Tender Grapes” with Edward G. Robinson and Margaret O’Brien.

A memorial service will be held this summer, according to his family.

Herman and Sonja Roberts with three of their grandchildren.