Well, Dave Chappelle has done it again.

His new Netflix special has not only captured the attention of millions across the nation, it has continued his ongoing crusade to open the doors and push the boundaries of acceptable public discourse in our pluralistic republic — especially surrounding the nature of sex and gender.

Chappelle really is a genius in how he effortlessly weaves in and out of the most hot-button issues imaginable. These topics can’t even be touched by most public figures, but his skill at setting up jokes, thoughtful distinctions, raw courage, and genuine love and care for those who disagree with him permits him to not only to touch — but to firmly grasp and expertly pick apart these issues.

That said, not everyone agrees with me about these judgments.

Indeed, because Chappelle’s complex and nuanced view (I encourage readers to do their research on what he actually holds) on the transgenderism debate doesn’t fit with contemporary orthodoxy on these matters, a number of their employees are staging a walkout in an attempt to coerce Netflix to take his shows off its platform.

There are plenty of folks, of course, who will see this as yet another example of our increasingly humorless society. If we can’t even joke about these matters, how will we ever get to the point where we can discuss them seriously? How can we claim to live in a pluralistic republic — one in which we welcome multiple points of view — if the greatest comedian of his generation can’t go after a live and important issue in the culture?

In response to these questions, I think it is important to acknowledge that the instinct behind many of Chappelle’s critics comes from a good place. They see what he’s doing as a kind of bullying — punching down group of people (those who identity as transgender) who are a radical minority and already deeply marginalized in the culture.

And a generalized anti-bullying concern is very, very important. Many aggressive interactions have until recently been dismissed as “someone’s sense of humor” or “joking around” — but they have real world consequences for people that may include self-doubt, self-harm, and even suicide. Indeed, today’s online bullying takes it up another level and is directly related to the increase of suicide, especially among young women.

Thank God, therefore, for recent interventions to take this problem way more seriously than we have in the past. 

But is the only alternative living in a humorless society? One where we can’t joke about things at all? That doesn’t seem right. Traditionally, discussion of the virtues presents them as the “golden mean” between two extremes. For instance, the virtue of courage lies between rashness and cowardice. The virtue of modesty lies between shyness and shamelessness. And so on.

Is there a way to live out a “golden mean” between bullying and humorlessness?

I think so. And the reason is because I’ve experienced something like it as a member of sports teams and also working on construction crews.

It is difficult to articulate — but it is even more difficult to understand if you, yourself, haven’t been a part of a community like this. There’s a kind of culture in play which makes space for “giving people [crap]” and poking fun at them — but in ways that really shouldn’t be described as bullying.

In fact, this dynamic is often used to signal to a younger person or newbie that they are part of the community — and also to validate their rise up the ranks of respect of one’s peers. It can also serve as a way of working through differences — and calling out problems. 

Sometimes there are just things that need to be said that, in other contexts, are just left alone to fester and toxify relationships and communities. But in a community like this, the dynamic allows difficult truths to be told in ways that don’t break the bonds of fellowship.

When the joking and poking fun crosses a line (as, let’s be honest, it sometimes does), the dynamic of the group is very often such that it polices itself — with veteran members of the community deciding that something has gone too far. And there’s even a check on those veterans, because when one of them gets too big for their britches, the joking and poking fun can bring them down a peg.

In healthy groups like this (and, to be clear, they aren’t all healthy), there is a kind of solidarity present. A culture of encounter. The willing of the good of the other, even as words are spoken that (on paper and isolated from the social context) seem to indicate the opposite.

Chappelle tries to do this throughout his comedy specials (and, again, I encourage readers to actually do your own research on this), showing that even as he is poking fun, and saying some things that need to be said, he genuinely loves and cares for those who identify as trans. He tries to show this explicitly through his story of friendship with a trans comic — someone who he clearly loved and supported, but with whom he had disagreements as well.

Tragically, it was only after his friend publicly defended Chappelle against the social media mob — and after she got dogpiled online for doing so — that his friend committed suicide.

Chappelle discussed creating a trust fund for his friend’s child and thought about what he would say to the kid one day. He came up with this: “I knew your father, and he was one hell of a woman.”

Signaling the kind of relationship and dynamic they said, Chappelle said, “She would have loved that joke.”

What’s the golden mean between bullying and humorlessness? I’m not sure I have a good word or phrase for it, but maybe it is something like “winsomeness”? A kind of good-natured, attractive, and funny way of speaking things that need to be said. But always with the love due the dignity of the human person squarely in mind.

Nobody does this better than Chappelle. And he lights the way for the rest of us.