Eleven years after he took a flying leap off the peak of success, Dave Chappelle returned to stand-up comedy in 2017 with a pair of Netflix specials called Equanimity and The Bird Revelation. Well, that’s almost true. He actually returned earlier that year with a pair of specials aired elsewhere. This may seem like splitting hairs, but those two earlier specials—more specifically their aftermath—are the story here. So, fast forward a couple of years to when, after another nightly conquest to get the kids to bed with minimal weeping and gnashing of teeth, my wife and I sat down on the couch needing a laugh. We cued up Equanimity and braced ourselves. What followed was almost exactly what we expected. Funny, observant, crass. It was also haunted by the specter of criticism Chappelle had received in the preceding months.

In the specials that predated the Netflix deal, Chappelle had kicked up a bit of controversy. He had made some jokes involving LGBT and transgender people that drew widespread ire. There is no doubt that Chappelle touched a raw nerve, but recall that on the other side of his absence from show business, Chappelle had been able to press hot button issues like slavery reparations, R Kelly, and drug addiction and get the laugh minus the heat. In Equanimity, Chappelle wondered if those days were gone and, if so, whether that was dangerous. He described the phenomenon as “brittle ears” (Timothy Thomas unpacks it well here). As Chappelle says in his routine, “Everything is funny until it happens to you.” People are sensitive and in new ways than they used to be. If I were to sum up the pushback Chappelle received, I’d say that his critics seem to be holding humor and empathy as two ends of a spectrum. And in this case, if you reach for humor on LGBT, transgender, and other sexual/identity issues, you are de facto reaching away from empathy. On that scale, of course Chappelle sounds wrong. Out of tune. But I don’t think that’s the best scale.

In his book Strong and Weak, Andy Crouch introduces us to a powerful tool to help defuse the tug of war we experience when trying to put two ideas in diametric opposition. It’s called a 2×2. Instead of making humor and empathy a zero-sum game, the 2×2 model says you can make jokes and have empathy at the same time. One isn’t an automatic reduction of the other, they can rise and fall independently. So, when we plot humor and empathy on a 2×2 (see image), we get four quadrants. In the top left, with high humor and low empathy, you have cruelty; the sort of which we find virtuosic in any schoolyard bully and most political pundits. In the bottom left, with low humor and low empathy, you have what I’d call indifference. It takes too much to laugh, it takes too much to cry. This is its own brand of meanness—maybe even a worse kind—but it’s a meanness of neglect, not aggression. In the bottom right, with high empathy and low humor, you have a tenderheartedness that raises its hackles. Sensitivity with sharp teeth. The top right of a 2×2 is always the most interesting because it’s where you are strong in two traits that may seem contradictory. But, before I get there, I should probably back up and actually convince you that having a lot of empathy without humor can actually turn out worse than you might think.

While you were out…

If you don’t already know Chappelle’s backstory, his standup comedy led to movies which led to his own sketch show on Comedy Central that was massively successful. By 2006 Chappelle was something of a titan in his corner of the entertainment industrial complex, basically printing money for Comedy Central in the form of DVD sales. Then, out of the blue and middle of the contract, Chappelle dropped the mic, quit the show, and vanished in a way that might not even be possible for a celebrity of his wattage to do anymore in our age of crowd-sourced, smartphone-powered surveillance. Over a decade went by without a peep. And then he was back, Netflix contract in hand. They say you can’t step in the same river twice, but I don’t think Chappelle set foot on the same planet.

In the 21st century, 11 years is a lot of cultural torrent flowing by under the bridge. When Chappelle left his show, Facebook was still only accessible with a .edu email address. For that matter, email was still a way college students communicated with each other. Barack Obama wouldn’t even declare his candidacy for the Democratic nomination for another seven months and Donald Trump was still a game show host (and not even for celebrities yet). #MeToo (aside from the fact that hashtags meant nothing outside of coding circles) sounded more like a name for a lame U2 cover band. All this is to say, in Chappelle’s absence, a whole heck of a lot of social upheaval took place, got uncovered, or otherwise came to pass in a brand new world where the 24-hour news and punditry cycle got flooded with a billion voices chiming in.

Dave Chappelle re-entered a pop culture universe that was reeling from social upheaval and subsequently, really cautious about what it laughed at. In 2020 we have access to far more information than even in 2006 and a lot of it is bad, hurtful, ugly news. At the same time, on social media we are all more transparent than ever with our interior lives, myriad individuals flying a million banners announcing us as the people we believe ourselves to be. Social media is a two-edged sword, though. Anyone can find like-minded community there for anything, and yet also be 100% accessible to vicious  assault and harassment. Our deepest vulnerabilities are at once exposed to acceptance and pummeling all while the news overflows with stories of abuse. You can hardly blame people for being on edge. It’s never a good time for schoolyard bully humor, but the way communication works now it’s arguably the worst time for that.

Chappelle, though, came back on the scene and did what he had always done. He told jokes about touchy subjects. I mean, this is the man who made a mint chiseling comedic diamonds from the immense and heated pressure of America’s racist history. One of the pillars of Chappelle Show was sketches that leaned so far into stereotypes that they became absurdly hilarious. See, for reference, his chaotic depictions of an imagined slavery reparations program, a scandalous black presidency, and a racial draft. Systemic racism and disenfranchisement aren’t exactly funny, and yet in 2006 Chappelle’s audience was able to laugh. By 2019, the laughter was notably muted (perhaps most clearly seen in Chappelle’s second Netflix special, The Bird Revelation, which gets downright uncomfortable at times).

Maybe Chappelle didn’t expect that sexual/identity issues to be more off limits than slavery, but I’ve watched Chappelle enough to know he’s too smart for his offenses to have been accidental. I would argue Chappelle saw his audience drifting into the bottom right of our 2×2, down into the regions where empathy gets really serious. He looked at a collective tenderness emerging in response to legitimate griefs and saw in Cancel Culture and Call-Out Culture the makings of a potentially toxic hypersensitivity. Brittle ears.

Empathy is, in a spiritual sense, feeling someone else’s pain. Hurt is a primary emotion. It’s one of the ones we feel deep in our bones and, once felt, can lead us to respond with one of our secondary emotions. Because hurt, well, hurts, it’s easy to respond with anger. Anger is a powerful shield. But, like all power, anger is hard to control and can easily turn around and do its own hurting. When social media takes up its pitchforks and shames someone into oblivion, this is anger in active response to hurt. One of the reasons it’s so powerful is because it feels righteous. It feels righteous precisely because it’s empathic. Tragically, it can become another phase in the cycle of hurt and retribution and hurt and so on. When it really gets under a full head of steam, Cancel Culture can look far too much like the hurt it’s trying to cancel. If you only look at actions, empathy without humor is damn hard to tell apart from humor without empathy. It just trades in mockery for shouting down.

Another Kind of Re-Entry

If Chappelle’s abdication of the comedy throne reminds me of anything, it’s a poem I dearly love: “Manifesto: Mad Farmer Liberation Front.” In it, an octogenarian Amish-ish farmer/essayist/poet/novelist from rural Kentucky named Wendell Berry offers advice to any listener who might want independence from economic or social or political forces that would, for their own convenience, desire a person’s mind be predictable and as he put it, “punched on a card and shut away in a little drawer.” Instead, he says:

Be like the fox
who makes more tracks than necessary,
some in the wrong direction.

Chappelle’s return to Netflix after making so many tracks in the wrong direction, then, takes me to another passage at the heart Berry’s poem: “Laugh… Be joyful; though you have considered all the facts.”

Chappelle strikes me as a man who has considered all the facts. His genius-level judo, then, is to get below anger to the hurt and fear underneath and then veer off into absurdities instead. In that way, he’s trafficking in a kind of redemption. Systemic injustice is perhaps more visible than it’s ever been and is often even boasted over in the public square. There’s plenty of hurt to be mad about. Anger—even righteous anger—can be poison in the bones, though, if left to fester. To offer laughter in place of anger is almost a ministry of grace; an upending of a long-standing world order. Laughter, I think, has the power to re-humanize us and this is what can happen in the top right of our 2×2 where empathy and humor are both present.

In our moment in history, in our corner of the globe, social norms are at a low ebb. Individual identity is royalty. And yet to be human is to be distorted. So, like all good and tragic kings and queens, we tend to be kind of vain. Able to laugh at everything until the joke is on us. If Chappelle is right, if our ears have grown brittle, then our royal court desperately needs a jester who can still say what nobody else is allowed to say out loud.

Chappelle’s best comedy holds, as it were, a fun-house mirror up to our nature. He’s at his best when he takes our human distortions to their furthest limits and asks of those in power, “Is this really what you’re so afraid of?” and, on the other hand, reassures the vulnerable and hurting, “To be human is to be ridiculous. Is that so bad?”

Even now, that’s hard to write. There’s been enough mockery and cruelty from enough public people that the case for laughter still feels slightly elusive. But, before we let the schoolyard bullies kill our sense of humor for good, let’s pull in one more voice. In The Human Condition, Hannah Arendt looks at the cycle of violence and retribution—hurt and hurt back and hurt back again. The cycle is nice and predictable, easily played for votes and dollars by those who care to do so, and it’s the kind of cycle that Berry argues is worth confounding. Arendt says the only thing that can break this vicious cycle is forgiveness. Though we have considered all the facts, when we let one of the hurts go by unanswered, our power of thought and reflection return. We can re-enter a fuller humanity and choose another way. When Chappelle takes a collective hurt and, instead of anger, turns to laughter, he breaks the cycles, and allows a hurt to go unanswered. He essentially says, “Even though you did what you could to tear me down, you have not predetermined how I’ll respond.” This is the degree of humanity—full in its resilience, free in the best sense—that can exist in the top right of our 2×2.

The thing I love about 2x2s is that the upper right quadrant so often seems to require something superhuman to achieve. To contain a paradox would require something transcendent. Perhaps, God himself. In the case of humor vs. empathy, it requires anchoring our deepest sense of self somewhere untouchable. In truly safe harbor, we can laugh at our troubles. Being there can make us resilient enough to take our royal selves less seriously. To laugh. To forgive.