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Mark Ralkowski is an assistant professor of philosophy and honors at The George Washington University. He wrote Heidegger's Platonism (2009) and edited Curb Your Enthusiasm and Philosophy: Awaken the Social Assassin Within (2012).

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Dave Chappelle is an institution, the most popular American comedian today. Also the most criticized. He tells a lot of racist, sexist and gender insensitive jokes. This makes him the perfect subject for a book called Dave Chappelle and Philosophy. Mark Ralkowski, a philosophy professor at George Washington University, put out a call for chapters of this book, and this is the result. Twenty-five chapters picking apart Chapelle’s style and work and significance.

Many of them spend their efforts trying to figure out why his jokes are funny, why we like him, and how he constructs his jokes, stories and TV specials. They are mostly out of their depth.

A lot of them don’t even get it. The real humor, the real point, escapes them. Some of the essays are bizarre. A few might have taken it too literally, trying to force Chappelle’s Jell-O into a Hegelian dialectics box, or a Kierkegaardian framework, or a Freudian analysis. One lectures readers on logic, posing the four possibilities of an abortion decision between a man and a woman. My least favorite has to be the chapter that asks the deathless question – what would (Saint) Augustine think of The Chappelle Show? Spoiler alert – he would appreciate it, the author says.

At the other extreme, there is a chapter called Revolution or Illusion, (by far the best) that asks the question is Dave Chappelle a revolutionary? Brandyn Heppard teaches philosophy at Raritan, and is passionate about comedy and revolution. His chapter is an excellent, organized and effective examination of where and how Dave Chappelle fits politically and socially. He says things like Chappelle “is not (there) to express his own reactionary views, but instead, to expose faux-liberal outrage. This is exemplified by Chappelle’s midjoke check-in, when he asks with glee, ‘Did I trigger you?’” This chapter offers the most perspective and challenges.

He says Chappelle is an exemplar of Late Capitalism and by definition, he is not only not revolutionary, but leads audiences away from revolution. This is thought-provoking and intriguing, since so many look to him for their inspiration on social issues, much as they looked to Jon Stewart for the news. He shows that Chappelle himself publicly denies revolutionary status or pretense, much as Stewart always denied being a journalist. He is all about joking. It’s just that he has a higher degree of self-awareness and intelligence than many if not most comedians.

He does not want to be stereotyped, reserving his right to joke about anything. Even when guest-hosting Saturday Night Live, he criticized producer Lorne Michaels, saying “I’m sorry, Lorne. I thought we were having a comedy show. It’s like a woke meeting in here.” This chapter alone made the read worthwhile.

There were so many angles to come at him, I had to watch the specials again to evaluate what the authors were saying, or trying to say. Watching that way, I saw Chappelle evolve from a skinny high school humor standup with a lot of swearing, to a beefy finely tuned humorist with a lot of swearing.

Dave Chappelle’s standup act today is scrupulously constructed. Chappelle has two similar joke patterns that he employs with devastating effect. He will talk about a pop culture or societal issue, to which the audience will roll its eyes and sometimes even groan. He tells the story, which might even have zero laughs in it, but then wraps it up with a reference to an earlier joke or to another story he weaves in, totally winning over the audience when it realizes he has made a massive point, usually ironic. The other variant is beginning with a seemingly innocent funny story and bringing it around to the a pop culture theme or societal issue, making a devastating point at the end, again, most often something hugely ironic. And winning over the audience completely. It is tight and total manipulation. And even a ringing cellphone does not put him off his script. He knows what works.

As a result, his audiences have come to realize they must listen attentively, because they will not know in advance what it is all really about, and that whatever he says at the outset will pay off in the long run in a very different way. This plays out over and over again for the whole set. It is a feat of engineering, a steel trap mind flashing its wares. The highly polished pieces slide together effortlessly, locking to each other without friction. It is fascinating to behold. Mia Wood’s chapter, called Dave Chappelle Knows Better Than That, comes closest to nailing this current patter of his.

Here’s an example of the structure, annotated by Chris Kramer, a philosophy teacher who wrote his dissertation on “subversive humor”. From his chapter, called Dave Chappelle’s Positive Propaganda:

“There’s only one thing that’s going to save this country from itself … Listen, no matter what they say or how they make you feel, remember, this is your country, too … And you know what we have to do. This is a f----n’ election year.” We can see where he’s going with this and applaud his highlighting the importance of everyone’s civic duties. He continues, “Every able-bodied African American, must register… for a legal firearm. That’s the only way they’ll change the law [gun control]” (Sticks and Stones). Ah, we have been misled, rhetorically disarmed but joyfully so, and not without some insight.

But there’s more to it. Chappelle’s bits are evolutionary. His early standup was not like this. What he has done, remarkably, is grow himself and grow his audience with him. Those who watch now have to focus. Thinking is required. The audience has had to evolve to keep up. This is an aspect no one wrote about here, but it is a big factor in the Chappelle story. He is now a far more commanding presence, a far more composed raconteur, and infinitely more worldly than the rapid-fire outrage comic he began as.

Thanks to the miracle of videos, critics are able to linger over Chappelle’s jokes and measure the weight of every word. They find words to criticize, assign them undue weight, and devise scenarios for what Chappelle “actually” meant in his word choice, if not the words he chose.

Most of the misguided criticism is over Chappelle’s insensitivities to women and LGBTQ+. It is not just these authors. Chappelle has had to add that he is joking, right in the act. He has had to remind the audience that he is here to “f..k around”.

But they posit far too much in ulterior motives to him: “The only reason people want to hear from people like me is because you trust me. You don’t expect me to be perfect, but I don’t lie to you. I’m just a guy, and I don’t lie to you. And every institution, every institution that we trust, lies to us.”

Let me tell you something. There is a comedian in Québec called Yvon Deschamps. For my money, the best it has ever produced. He was a Chappelle-style comedian, twisting stories and endings, using misdirection, irony, satire – everything we love Chappelle for – but in 1970. Very topical, very political and very politically incorrect. His Blacks were the French native Québecois, always the underdogs, always looking up from below, and not very ambitious. He often said that the highest goal of a Québecois was to have a car. Then everything would be perfect. He was set for life.

In the final bit of a one man show, Deschamps rails against racism and discrimination. He blames it on intolerance. People are intolerant of others – other languages, other cultures, other skin shades. They are selfish and self-centered, and don’t empathize. He goes on and on until he end ends up yelling at the audience “Death to the intolerant!” (“A mort les intolérants !”). He won’t stop, and half a dozen stagehands come out to carry him off the stage, still screaming, calling for death to the intolerant. Chappelle would understand.

But here’s the point. In an interview Chappelle could relate to, Deschamps explained how it was he could slur and offend so many groups in his act. He said that when he told jokes about the English, or the police for example, people laughed, so he knew they weren’t really against them. But when he told jokes involving Jews, there was no laughter. Les Québecois were still firmly anti-semitic and nothing about Jews made them comfortable enough to laugh. They squirmed, hoping he would just move on to something funny.

I have never forgotten this lesson, and Dave Chappelle clearly operates by it. His jokes involving women, LGBTQ+ or victim-blaming are still funny to most, because Americans (and especially Blacks) know there is injustice everywhere, and some things are so absurdly out of whack, you can only laugh, or you would cry. Americans are pro gay marriage, pro-choice, and saddened by victims. Those jokes hit home. It’s only when nobody laughs that Chappelle will stop telling those stories, because the haters will be in charge. Chappelle is not an instigator, he is a barometer. He is not a crusader; he is a merchant. If the goods don’t move off the shelves, he won’t stock them anymore.

What this book did was to give me a far greater appreciation for Dave Chappelle than I already had. It made me watch differently as he performed over the decades. It made me appreciate the evolution of his delivery. And most of all, it made me appreciate how deep Chappelle goes in what would normally be a topical gag.

The book, on the other hand, is all over the place, with a lot of pseudo analysis that goes nowhere. Whether or not Chappelle’s joke fits a Hegelian dialectic tells us nothing at all. Freud’s castration theories are irrelevant. It turns out this book is one of a series of ten so far, examining what philosophy has to contribute to pop culture. So there is Queen and Philosophy, Pokémon, Punk, Dark Souls, Neon Genesis Evangelion, and Better Call Saul titles, all from the same publishing house, Open Universe.

The best I can say is that Chappelle inspires so much word crunching, he must be worth it.

David Wineberg
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DavidWineberg | May 4, 2022 |

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