Dick Gregory Fought For A Different World Through Comedy

Remembering comedian and cultural icon Dick Gregory's brilliance and bad jokes.
August 25, 2017, 7:57pm

Postscript is Cameron Kunzelman's weekly column about endings, apocalypses, deaths, bosses, and all sorts of other finalities.

The comedian and cultural icon Dick Gregory died on August 19th, 2017. A complicated figure, Gregory broke into national success during the 1960s, and was both a prominent member of the civil rights movement as well as a frequent attendee at the Playboy Mansion. This, I think, gives a sense of the complicated racial and gendered dynamics that surrounded Gregory, the kind of figure who produced jokes like this in 1962: "Some people have a wonderful way of looking at things. Like the ones who hire one of us to babysit so they can go to a Ku Klux Klan meeting."


The core Dick Gregory joke, the one that summarizes so much of his talent and thought, is on the album In Living Black and White.

It starts out as benignly as possible: JFK was recently elected, and Gregory advocates for a switch to bingo, instead of President Truman's piano playing and President Eisenhower's golf. It is, to the best of my knowledge, a joke about Catholics and bingo, a comedic setup that is so profoundly foreign to me that I can only measure the laughs and try to puzzle my way backward from there. After all, this is a comedy album released in 1961. The past is a foreign country.

At this point in the routine, a white woman interrupts Gregory. This is standup, and this is standup form a black comedian in 1961. Heckling was not encouraged then any more than it is now, and the racial implications are serious in this instance.

He identifies the paradox of the world, mostly in how we think about race, and then he pulls it apart.

Set the scene in your mind: Gregory, profoundly successful nightclub comedian, is a black man. In an almost-unthinkable feat of will and social maneuvering, Gregory jumped out of deeply segregated performing models, most concentrated in terms like "chitlin circuit," and into white clubs and integrated rooms. Again, this album released in 1961, and was recorded before that. We're years away from the Civil Rights Act of 1964, the assassinations of President John F. Kennedy, Malik Shabazz (Malcolm X), Martin Luther King, Jr., and the conservative turn of the 1970s. There's some hope, here, in 1961.

The white woman interrupts. "Eight years of golf wasn't too bad either!" she says, clearly with some love for Ike in her heart. Gregory counters immediately: "I'm not knocking golf or nothing like that, honey, I don't even give a damn! I just barely got to vote this time!" The crowd roars. He keeps going: "See, you've been voting for a long time, I haven't. Back in my home town, they make us take a test to vote. Nuclear physics in Russian. If you pass the test, they tell you 'Boy, you can't vote, you read Russian, you must be communist."


This is the quintessential Dick Gregory joke. He identifies the paradox of the world, mostly in how we think about race, and then he pulls it apart. And, most importantly, it's not in the abstract. This white woman in the audience is asserting her right to interrupt Gregory, the professional comedian, and he can't just shut her down—that's not in the playbook of a black man in 1961, even when he's on stage holding a microphone. But he can re-assert himself as comedian-in-his-prime, as an entertainer. So her interruption gets folded in and made part of the joke, which cleanly flows back into what Gregory had working for him.

His comedy was like water. It moved, constantly, and it wore down everything in its path until the American comedic landscape couldn't imagine itself without the way he thought, the way he presented the world, in it.

Pointing out hypocrisy, injustice, and the paradox of American racial politics was an extension of who Gregory was.

He created media, like many of us do, that tried to intervene in the common sense of the world. He wanted to shift not just racial politics, but the very terms that racism established itself with. Gregory's comedy was a method of talking back, forcefully and clearly, against the assumptions about the racial order of the world. "When I left St. Louis," he once wrote, "I was making five dollars a night. Now I'm getting $5,000 a week for saying the same things out loud I used to say under my breath." Pointing out hypocrisy, injustice, and the paradox of American racial politics was an extension of who Gregory was.

I'd be doing you a disservice, though, if I didn't relay the back half of the joke above. "We won that election for Kennedy out there on the south side," he says. "We're out here voting six or seven times. We don't mean to cheat or nothing, we're just trying to make up for them times we couldn't vote. You read it in the paper didn't you? 87 people registered, 102 vote, and two live in the neighborhood." A little bit of filler talk, and then: "Republicans doing the same thing, but they don't use us. [They use the] Chinese." This turn to racism, to the easy outlet for the laugh at the expense of his enemies, is also as much of Gregory's act as any of the positive things I mentioned above.


Dick Gregory's stamp on the American consciousness shouldn't be understated, especially since so many people are familiar with his form of comedy without knowing his name. He pushed the envelope, constantly, and it often went places that we're profoundly uncomfortable with today. Watch a few interviews with him and you'll get big doses of misogyny, respectability politics that hinges on shaming poor black people, and health guru information that suggests that changing your diet will cure you of cancer. Gregory had a lot of very bad opinions and thoughts that were backed by an amazing quick wit and a Herculean willpower.

He ran for President as a write-in candidate. He personally funded research into the assassination of Martin Luther King, Jr., and he wrote multiple books about it. He asserted, time and time again, that King was killed by the United States military. I saw him speak once, and he stood there in a packed room and asserted that he had proof right here of the assassination. He also thought that the American government lied about 9/11.

I'm not trying to paint a picture of a brilliant comedian who went off the rails into conservatism and conspiracy. Rather, I'm suggesting that same force of will that allowed Dick Gregory to ascend to the heights that he did also did not leave much room for personal second-guessing. He took in information, made decisions about it, and was inflexible in those decisions. If his comedy was water, then he was a river, and he carved a path through the landscape of America. It was singular and his own.

Dick Gregory was a man who saw the slow changes of the 20th century. He lived under Jim Crow, came up out of extreme poverty, witnessed the struggle for civil rights, and then witnessed the slow dissolution of many of those rights. The final page of his autobiography reads this way: "This is a revolution. It started long before I came into it, and I may die before it's over, but we'll bust this thing and cut out this cancer."

I don't know if Dick Gregory thought we got there, if we busted this thing, but I wonder if he saw any hope.

You can follow Cameron on Twitter.

Have thoughts? Swing by Waypoints forums to share them!