The best Dick Gregory story is the time in 1961 when he got up in front of a largely white audience and delivered the joke about the white waitress at a restaurant in the South telling him that they don't serve colored people. The joke ends: "That's all right. I don't eat colored people. Bring me a whole fried chicken." It is hard to know now how many people laughed.
Or maybe the best Dick Gregory story is the one where he ran for mayor of Chicago in 1967, a campaign during which he was arrested by United States Treasury agents for printing and handing out fake dollar bills with his picture on them as a part of his campaign literature.
Or else the best Dick Gregory story is the one about how, in 1971, he went without solid food for over two years to protest the war in Vietnam—once running 900 miles, from Chicago to Washington, D.C.
Black comedians in America have the luxury of telling jokes the same as all other comedians. But somewhere in their careers, all comedians decide whether the jokes are going to be more than just jokes; either hard commentaries, or a way of archiving community, or a way of healing pain, or a way to help guide important dialogues, or a combination of all those things. It bears mentioning that Dick Gregory spent only a portion of his life making a career of stand-up comedy. But that portion, most of it in the early 1960s, was a time when most black people weren't telling jokes in white clubs, and definitely not telling jokes to white people about white people. Gregory was able to cross over to white audiences successfully, and he somehow did it without really bowing to those audiences, or toning down the way he articulated his discomfort with the world.
At its best, comedy is equal parts truth-telling and storytelling, so there is no mystery as to why Dick Gregory excelled at it. Still, at his core, he was an activist, a forward-thinking revolutionary who just happened to know how to spin a tale rich enough to keep people laughing. He isn't the funniest black comic who ever lived, but he set a blueprint for what a black stand-up comic could be; in the end, he felt like a man gathering an audience around a porch in any neighborhood in any city, to talk loud and long about the state of the world, and kick in a few laughs underneath it all. Because I saw Gregory's influence in Richard Pryor, and because I saw (and still see) Pryor's in Dave Chappelle, and because I will surely see Chappelle's in someone who will come along years after him, it feels good to know that Dick Gregory's blueprint will exist beyond him.
More than that, though, Gregory established a place for black entertainers to be vocal about the world's many injustices. Looking at his career timeline, it starts to seem like comedy was simply an entry point to get up in front of people and speak about the ills of the world. Dick Gregory would hold court wherever there was a court to be held, and that, too, is stand up, whether it was on a stage, or in politics, or in resistance to anything that struck him as unjust.
There are no comedians like Dick Gregory anymore, perhaps because we've become so used to the comedian as a vessel through which we laugh to escape pain, while we look elsewhere to be moved toward action. I suppose this is fine, or at least it's an inevitability of our shifting times. We don't hold our comedians to the same standards that we used to. Punching down is all too often forgiven in the name of cheap laughs. Theoretically, we live in an era of political comedy—or at least an era where comedians are making political jokes. But so many of these comics have a single aim: to make fun of the president without addressing the structures that put him in power. I do still want to laugh. I want to find things funny, and while I am fine with romanticizing the past, I often want to make sure that it is, in fact, a past worth romanticizing. I say all of that to say that Dick Gregory was worth it. Dick Gregory was exactly what you thought he was, and probably more. He was a man of no easy exits, just greater, more complicated doors in.
Dick Gregory used comedy as one arrow in a quiver of many. He engaged politicians directly, repeatedly fasted to protest injustice, ran for office, and (literally) ran across this treacherous American landscape. All in the name of tipping the scales a little more toward something that one day might look equal. It is infuriating to me that Gregory is now dead, in a year where he must have looked at this country and wondered if anything he did moved the needle at all. It is heartbreaking to think that he is gone, and to imagine that he died in an hour where people were debating what gentleness we should afford neo-Nazis, or how similar white supremacists are to the people fighting against them. There is nothing romantic about that—to leave behind a world that still seems like the one you spent decades chipping away at. But I hope that Dick Gregory left us with an understanding of his true worth: his ability to show a country its ugliest reflection and not let it turn away. To allow a country to laugh at its ugly moments until it cried, until it became angry, until it decided to clean up where it could.
The best jokes make you laugh, but then don't leave you behind. They wrestle with the interior of the moment into which they were born. And, oh, are we in a moment. We are truly in it now, and we need the jokes that punch anywhere but down. We need the jokes that punch and do not stop punching, and the comedians who refuse to settle for cheap grins or cheap controversy. Injustice is only funny if, through humor, we can shake toward the truth of how awful it is. That was Dick Gregory's defining trait. He was always reaching his hand into that gap between humor and rage, offering to pull anyone willing across the wide chasm. And that is the best Dick Gregory story. The one where he left behind a body of work to light a whole path for a new generation of comics, and of activists. The one where he is still two arms, reaching across a widening gap.