I met Dick Gregory at the exact place where you’d expect: a protest. I was in Ferguson in 2014 when I first had the opportunity to share a few moments with a man whose comedy many have forgotten, but whose work still benefits us all. But being remembered was not his aim that day; the St. Louis native wasn’t there to be seen, he was there to see about his people. My mother likes to joke that Gregory looks like he could be my father, especially with his longer, but it is our shared passion for activism and careers on comedy.
Dick Gregory could have been one of the wealthiest comedians of his time. As the first Black man to sit on Jack Paar’s talk show couch, the entertainment world was his for the taking in the early ’60s. He was funny, cool, politically literate, and—despite his militancy—endlessly approachable. But too many people who looked like him were suffering, and he knew there was work to do offstage. Choosing to center his politics cost him mainstream success, but endeared him to those on the margins. He didn’t so much as turn his back on entertainment as he turned his whole self to us. His audiences laughed at his satire, but once he actively fought to change the same system he’d made money ridiculing, those audiences thinned. But if he regretted the loss of income, he never showed it publicly. That sense of purpose—the discipline to walk toward uncertainty and away from ease because of his principles—made him more important to me than my other favorite comedians.
Back when I thought “intersectional” was a type of couch, Dick Gregory already knew that the struggles of marginalized people were tied together.. He wasn’t just involved in the Black Civil Rights Movement, he also participated in actions for women’s rights and against South African Apartheid.
Even when I disagreed with Mr. Gregory, I learned. His blind spot around homophobia meant he was my first “problematic fave,” but it also helped guide my own still expanding understanding of equality. If he could accomplish all that he did while remaining anti-LGBT, how much could we do if we embraced all marginalized people and fought for equality with no qualifiers?
When I decided to do stand-up comedy in 2010, I knew that there was a particular way I wanted to do it: I wanted to make people laugh and say things that mattered. Because of Dick Gregory, I didn’t have to blaze my own path. He’d stood in front of America at a much more dangerous time and called them out on their shit. If he could challenge the status quo at a time where outspoken plus Black could easily equal lynched, surely I could speak my mind freely in a room full of hipsters waiting for their craft brews.
I had the privilege of meeting Gregory a second time in 2015, when he gave a stand-up performance at the Promontory, a mostly Black venue in the city’s largely mixed Hyde Park neighborhood. Gregory was as sharp as ever, delivering a set that was equal parts hilarious, poignant, and important. He mixed one-liners with political observations and conspiracy theories in a special kind of lecture-slash-stand up performance that few could pull off. I remember thinking, “This is the most Dick Gregory thing I could ever experience!” Later that year, I launched a monthly comedy show at the Promontory with my writing partner, Dave Helem. In fact, on the night that I saw Mr. Gregory, I began the discussions that led to the creation of my show. Maybe that’s not a coincidence.
After that night, I got the sense that I might not see him again. Not because of anything he said or did. It’s just that as I’ve aged, I’ve learned not to take these types of things for granted. He was 82 years old and touring with a schedule that would wear out much younger comedians, and I knew this couldn’t go on forever. For two years, I was glad to be wrong. He did shows in Atlanta, New York, Virginia, back to Chicago—he worked more than I did!
Part of me feels like Gregory lived so long that we forgot how important he was. We lost sight of what he gave up to become…this. He was a fearlessly outspoken champion for civil rights who refused to stop fighting until the war was won. Would any of us give up the possibility of being a big name comedian to make sure other people could vote? Would we walk away from guaranteed money and fame to help end an unjust system in a whole other country? Hell, could we even just be funny while discussing things that make most people uncomfortable? Dick Gregory did all of that for nearly 60 years. We’re all fans. But in a country that is just now getting around to tearing down monuments to men who fought to keep slavery alive, these words don’t do justice to the legacy of a man who dedicated his life to justice. Rest easy, sir. You earned it.
“I chose to be an agitator. And there’s one interesting thing about being an agitator—and I tell people—the next time you put your underwear in the washing machine, take the agitator out, and all you’re going to end up with is some dirty, wet drawers.” –Dick Gregory