Catching Up With Dick Gregory in a 2016 Interview!

He Killed Sacred Cows and Performed With Love at Mister Kelly’s

It’s the day after Christmas, 1962, and comedian Dick Gregory is hitting the road again. He’s a popular guy, always on his way to New York, Chicago, LA—he doesn’t always have time to stop at home to see his family for the holidays, but he’ll make sure he sees his wife today. She’s been in a Georgia jail since Christmas Eve.

There had been a sit-down demonstration at the Toddle House diner for almost a week, ever since a group of black people were refused service after a nearby event with visiting Kenyan dignitaries, but even so, the restaurant’s management probably didn’t have any idea what was about to hit them when she walked through that door.

The Jim Crow laws had been stricken from the books in the city of Atlanta, but attitudes were holding on, and this was still a whites-only establishment. Here was a trio of black women on Christmas Eve, cozying into a booth and checking out the menu with no intention of leaving when asked. There’s a relatively simple solution for this type of behavior in the segregated south: arrest the protesters. The charge? Conveniently, trespassing.

24 people are now in jail, but management hadn’t anticipated a couple of factors that complicate their strategy in a rather embarrassing way for the Toddle House, not to mention the city’s Mayor: one of the arrestees owns stock in the restaurant chain. And another detail: Ms. Lillian Gregory is married to one of the biggest civil rights freedom-fighting firebrand-wits in the nation, now speeding through the sky on his way to the scene of the crime.

Lillian is six months pregnant with Gregory’s third child, and has been on a hunger strike for 48 hours. The court sent a doctor to attend to her after she was apprehended, which perhaps was the decent thing to do in an otherwise indecent situation—but somehow she found the idea of a gynecological exam while in prison unappealing. She has received no medical attention while behind bars.

Today is her day in court.

You might expect Dick Gregory to really wind up the crowd on an occasion like this. I mean, if anyone would have some choice words for the situation, it’d be him. He’s the guy who kicked off his career with jokes like “A southern moderate is a cat who will hang you from a short tree.” But he’s not cutting up today.  He’s talking to reporters, but he’s measuring his words, stating simply that her children miss her, but she talked with them on Christmas Eve, and they understand the situation.  

We don’t know the unspoken rants—or the fears— running through Dick’s head, as she faces the court, but here’s what we do know: After this hearing, Lillian will be released from prison, blacks will be served at every one of the restaurants in the chain that owned the Toddle House, and none of this will make Dick miss his performance run at the nation’s comedy hot spot: Mister Kelly’s on Rush Street in Chicago that very night.

Dick Gregory was a serious and dedicated professional in a frequently silly world. His big break came from Hugh Hefner on a night when he got off at the wrong bus stop accidentally, and ran through the snow to get to the Playboy club on time for a show. He got up on stage and proceeded to kill in a room full of Southern businessmen—not exactly the friendly demo for a black man in 1961. In another instance he was in a car accident, and after a quick stop at the doctor’s, he made it to the mic to break a leg (figuratively) at Mister Kelly’s that very night.

For many younger people, Gregory’s prominence may have been eclipsed by the tabloid adventures of his contemporaries, Bill Cosby and Richard Pryor. To current generations, he is perhaps the least “Hollywood” of this triumvirate of famous black comedians who broke sharply from the tradition of black stereotypes in comedy and emerged on stages in the early ‘60’s. In Ebony Magazine, October 1960 Steve Allen said “Just imagine a Negro comic getting up on a stage and saying some of the things that Lenny Bruce or Mort Sahl are getting away with.” Imagine they did. They poked fun at the absurdities of racial attitudes and politics, and they proceeded to rule their decade with jokes that were consciousness-raising, unabashedly political, and still very, very funny.

Gregory was once described by a Chicago critic as a killer of sacred cows.  He’d cut his teeth on amateur performances in the army, and he developed a dry, off-the-cuff style where stories about seemingly unremarkable events were expertly punctuated by surprise punch lines--often jabbing back at common subtle or overt racism. He had a keen awareness of subtext and human motivation. His first book was titled Nigger, and in it he stated that his slave ancestors could rest easy knowing that any time the word was used it was advertising his book.

All this made him exactly the type of guy that my dad, George, and his brother, Oscar, wanted on stage at their club, Mr. Kelly’s. They had a philosophy of inclusiveness, and that was extended to black performers, staff, and customers, and they certainly had no fear of political provocation—just ask Lenny Bruce and Shecky Greene!

Gregory’s first run at Mister Kelly’s met with great reviews. The Chicago Defender published a piece that said: “Two years ago, Gregory skyrocketed from an obscure, struggling existence, to national acclaim. Today, he is considered the best of the crop of ‘standup’ Negro comedians. His esoteric wit and barbs discrimination and segregation has become his hallmark. He is also one of the nation’s highest paid entertainers.”

Another said: ”Dick Gregory, who has received a hot tip that the meek do NOT inherit the earth, will set forth--with plenty of plausible pleasantries-- his scheme for making sure that they’re invited to the reading of the will, at Mister Kelly’s on Monday, Dec. 17 for three weeks.”-The Chicago Defender, Dec. 15, 1962

Gregory’s run at Mr. Kelly’s was followed by eight years of whirlwind success, deepened by his Civil Rights activism. He essentially put aside a multi-million dollar career to dedicate time at picket lines and marches, and, like his wife, in jail cells.  He even ran for president!  Earl Calloway in the Chicago Defender said of him: “he has emerged from the classification of comic and has become one of America’s greatest entrepreneurs of humanity.” After all those adventures we were lucky enough to have him return to the club for a victory lap in the early ‘70’s. As before, The Chicago Defender did an excellent job of describing him.

Here are a couple of the best quotes from their Big Weekend Edition on May 2, 1970:

“The first black comic to comment on the social conditions, lifestyle, and attitudes of black people in America returns to the Chicago entertainment scene on Monday, May 4, for a 3-week date. Appearing on the bill with Dick, will be vocalist Marion Love….In a field where black artists were long subjected to being demeaned and made white by shortsighted entrepreneurs, Gregory emerged as one of the first to imply, through his attitudes and material, an overwhelming feeling of black--and human-- pride.”

“Through all his activities for peace and freedom, Gregory still retains his essential sense of humor and human warmth. He still enjoys himself and finds great satisfaction in making his audiences feel good. A serious subject given the Gregory touch is sure to have the audience laughing as well as thinking.”

--The Chicago Daily Defender (Big Weekend Edition) May 2, 1970

At 83 he’s still a ubiquitous force in several media channels, memorable for his luxurious white beard, killer side-eye, and his ability to talk at length on political subjects. He’s been doing plenty of appearances on TV, radio, and online content, sharing jokes, observances, conspiracy theories, and philosophical thoughts to help make the world a better place. He even has a wellness company called Health Enterprises Inc. that promotes vegetarianism for African Americans, and a Caribbean Diet for Optimal Health. There really is no nutshell description of this guy! Most recently, John Legend is producing an off-Broadway play based on Gregory’s life and comic genius called “Turn Me Loose” starring the great Joe Morton.

Gregory has always had fun, but he also has lived his life with a sense of purpose and an overriding love for his fellow human beings, and that’s what made him a truly special and beloved national figure to this day. I’m thrilled to announce that I had the opportunity to sit down with him for a recorded interview, which is part of the research for my documentary project about Mister Kelly's. It was amazing to hear his memories of the old times, and of my family. Lastly, check out one of his recent appearances HERE.