Photo: Mathieu Bitton/Netflix

2017, a year newly in the past, saw Dave Chappelle celebrate 30 years of doing stand-up comedy. He honored the occasion by releasing four stand-up specials, the latter two — Equanimity and The Bird Revelation — released on New Year’s Eve. Each displayed a mastery of the craft, and validation of the claims that he is the best stand-up alive, if not ever. And yet underneath the praise there was a murmur of frustration that quickly turned into outrage, whether it was for his perceived transphobia, homophobia, or, in his most recent special, The Bird Revelation, for partially blaming victims in a recent spate of high-profile sexual-harassment cases. People can argue this is on the audience — they are either too sensitive or not sensitive enough, depending where you fall. But stand-up is a medium defined by controlling how the audience receives information, so if there are wildly different reactions to the material, you have to look at the source. And the reason audience responses have varied so wildly stems from an indecisiveness on Chappelle’s part about how he wants to be perceived. Present-day Dave Chappelle wants to be taken seriously, except when he doesn’t, and therein lies the issue.

Comedians do not have to be right. Though some people might prefer comedians they agree with, being correct is not necessarily part of the job description. In fact, there are reasons for comics to be wrong. While humans, in our everyday lives, generally try to present what we think is right, our brains aren’t so tidy — they harbor a lot of thoughts our higher mind doesn’t agree with. Comedians poke at that messiness, offering relief from your own demons. That, or a comic might be wrong simply to get a rise out of people. Both make sense on a theoretical level. To take one theory: People want to be agreed with, so it is a “benign violation” for a comic to be publicly disagreeable. As a result, it’s on the comic to decide how benign they want the joke to seem, and how they go about communicating that to the audience.

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A comic — like early Sarah Silverman — can try to convey that she’s essentially playing a character that is wrong about everything they say, couching any racist material in deep irony. Another option is what Bill Burr, maybe the comic currently best at being wrong, does, getting people to laugh at things they might disagree with by using certain concessions— like “I’m an idiot,” “I know, I’m wrong,” — to walk back harsher claims. Or take the best stand-up special of last year, Jerrod Carmichael’s 8, which was itself a sort of meditation about wrongness. He doesn’t just make jokes about global warming not being a big deal; he investigates why he doesn’t care. This tells the audience that he is not trying to convince them of anything, as much as offer himself as a surrogate for safely exploring negative thoughts. On the other side of the coin, take a comedian like Big Jay Oakerson, a terrific joke writer, who likes to revel in offensiveness with an infectious “who gives a fuck” attitude — if you don’t like it, it’s on you.

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Chappelle, over the course of the four specials, does a little bit of all of these things, but with his most recent two, he seems to be specifically motivated by wrongness. So much so, midway through The Bird Revelation, he offers this call to action to comics: “Everybody gets mad because I say these jokes. But you have to understand this is the best time to say them. Now more than ever, I know there’s some comedians in the back — motherfuckers, you have a responsibility to speak recklessly, otherwise my kids might not know what reckless talk sounds like. The joys of being wrong. I didn’t come here to be right, I just came here to fuck around.” This isn’t true. Well, the first part — that for stand-up to be on the front lines of free speech, comics need to be allowed to be wrong (especially when working out material) — is; but to my ears, that last part sounded like a lie.

Chappelle is not just a comedian people go to see “fuck around” onstage. Arguably, he once was, but a transformation happened after he quit Chappelle’s Show because of the discomfort he felt with how certain white fans were laughing at his racial material. A mythology was built, best typified by Rachel Kaadzi Ghansah’s incredible, National Magazine Award–nominated piece for The Believer. The silliness that dominated much of Chappelle’s act was deemphasized for a reading of him as a pointed cultural critic and thinker on race relations. Early Chappelle was incredible at offering very ridiculous comedy, and slipping in trenchant social commentary when you don’t expect it. Take his bit about R. Kelly peeing on a 15-year-old from 2004’s For What It’s Worth. There are a lot of disagreeable, contrarian, punching-down thoughts in here, but his tone throughout the 5 minutes, and the 55 that surround it, is that of someone “fucking around,” so it’s easier to swallow.

It’s not just that the audience’s perception of him has changed though — it’s that Chappelle has undoubtedly leaned into being taken more seriously. His stand-up is now filled with long, laughless monologues that sometimes build up to jokes, but sometimes don’t. Chappelle has always had an unprecedented level of comfort onstage. He’s able to exist up there without laughs for longer than anyone, and the audience has always been comfortable indulging this. But since returning, he has used this power to make serious points. You can’t retell the story of Emmett Till, as he does in Equanimity, or the story of an exploited sex worker, as he does in The Bird Revelation, and act like you only came to fuck around. (Not to mention, the pretentiousness of the titles themselves.)

More simply, it’s extremely hard to have an audience see you as smart and dumb at the same time. Chris Rock, for example, has always positioned himself as smart. He broke out as a social commentator, and he wants all his material taken seriously. He might have had difficult-to-accept material throughout his career, but it’s always argued as a thing he thinks is correct. A step further was Patrice O’Neal, who specifically went out there trying to get people to laugh at things they didn’t agree with. Both excelled at creating a frame of reference where an audience member could laugh at something against their better judgement, where you laugh at the comic’s line of reasoning, not because they’ve convinced you. In both cases, the perspective is clear.

The problem Chappelle faces is similar to the one Amy Schumer did after she positioned herself as a leading feminist comic, despite having a lot of ironically dumb and offensive material in her past. Trying to balance two personas at once like this is like what happens in a bad sitcom when a character asks his identical twin to stand in for him for a presentation or a date — something will feel off. In The Bird Revelation, Chappelle presents a joke where he says a Louis C.K. accuser who had her comedy dreams ruined has a “brittle-ass spirit” in the same way he does information he seems to actually be arguing for, like his argument that women need to not scare away men who want to be allies. He doesn’t change his tone, but asks people to know when he’s just joking. You can see his ability to do better when comparing the trans material in his first two Netflix specials to that in Equanimity. Though frustratingly defensive, at least it’s clearer in the the later show that he is looking inward as opposed being prescriptive. In all cases, it’s not the audiences’ “fault” if people are taking parts of his material seriously that he doesn’t want them to — it’s a failure of communication; it’s a failure of being a person onstage who can encompass both. Chappelle is essentially asking the audience to take him seriously, but not literally, and just like with Trump, it’s not so easy.

I should clarify that I’m talking about two audiences — the live one in front of him, and the one who will watch the special at home. I say this because after I wrote about how I perceived Chappelle’s trans jokes at this summer’s Radio City show as failing, multiple comics I spoke to who were there told me they strongly disagreed. Their point is that it’s hard to be around people laughing at jokes and then read someone later say they didn’t work, as comedians depend on the audience’s reaction to determine what in their act is working. I understand this perspective, and I think they are correct — if you never intend on filming and releasing the material. This is because a live audience is in a very different mind set than a person watching comedy alone on their laptop. First, they are surrounded by other people laughing, which communicates that it’s okay to laugh at something they might not agree with. Also, the audience at a show like Chappelle at Radio City paid over $150 to be there, so cognitive dissonance may make them more likely to laugh — I wouldn’t spend this much money on a comedy show that I didn’t find funny — not to mention, if you are paying that much, you’re likely a fan, already onboard for wherever he takes you. (I do think this is why stand-ups get worse when they get really big. They don’t have to work as hard to get laughs.)

What Chappelle loses in the shift from one audience to the other is the benefit of the doubt. I am dubious of the belief that audiences are more sensitive these days, but I do think they are less likely to assume the best intentions of the person onstage. Whether it’s because of how the internet democratized who has a platform, so audiences don’t instantly give comics authority, or recent revelations about two of the previously most respected comics ever, I’m not sure. Either way, comedians have to work harder to earn an audience’s trust.

When I say this is a problem Chappelle faces, I mean it’s a conundrum. He may be the most talented comedian working today, but insomuch as we judge comics by their specials, the muddiness of his point of view at any given time will continue to handicap them. The good news is, since he says in Equanimity that being “too goddamn good” at comedy makes him think about stopping, maybe it’s enough motivation to keep him around, to see if he can do better.