Is the Joke on Dave?

Dave Chappelle continues to exhibit questionable behavior.

Dave Chappelle is a very funny man.

At his best, he is funny, incisive, and biting.

He can wittily and hilariously depict both the banality and pitfalls of racism, sexism, and drug use.

Lately, though, Chappelle has been more successful at unfunny, head scratching behavior. It is understood that many of today’s most lauded comedians court controversy as if their lives and careers depend on it. But at times, his words and actions seem less like someone who wants his name in the news, and more like someone who is living life via stream-of-consciousness.

His transphobic, antisemitic jokes have created controversy. While he expressed sympathy for a transgendered comedian who defend him, his comments still rankled many inside and outside the trans community.

There has been no such leavening of his anti-Jewish jokes. Those were expressed without any mitigation, especially his recent monologue while hosting Saturday Night Live. The monologue he performed during a cast practice was not the one he gave during the broadcasting, obviously knowing how network censors would react to what he would say.

I will not repeat his short-sighted jokes. Nothing good will come from their retelling.

His comments at his former high school, which was planning on naming a theater after him, was embarrassingly infantile. When a Q&A session with students went south with some of them calling him a “bigot” and “childish,” he responded to those and other comments by saying

“I’m better than every instrumentalist, artist, no matter what art you do in this school, right now, I’m better than all of you. I’m sure that will change. I’m sure you’ll be household names soon.”

At another event at the school, he accused the students of being “instruments of oppression.” He said:

"When I heard those talking points coming out of these children's faces, that really, sincerely, hurt me. Because I know those kids didn't come up with those words. I've heard those words before.

The more you say I can't say something, the more urgent it is for me to say it. And it has nothing to do with what you're saying I can't say. It has everything to do with my right, my freedom, of artistic expression. That is valuable to me. That is not severed from me. It's worth protecting for me, and it's worth protecting for everyone else who endeavors in our noble, noble professions."

Then, there was his actions concerning his hometown of Yellow River, Ohio. Chappelle had planned to build a restaurant and comedy club in the town but balked when multifamily affordable housing was added to the expansion. He spoke against the new housing at a town council meeting, berating the council as “clowns,” and reminding them that his business brought in $65 million a year. The council subsequently deadlocked during the council vote, so the housing change didn’t pass.

The most recent curious behavior of Dave Chappelle occurred at a recent show in San Francisco. The Bay City is also the headquarters of Twitter, and the crowd was shocked and then angered when Elon Musk, the company’s CEO was brought on stage by Chappelle.

A predictable torrent of boos followed. Musk responded by proclaiming, “I’m rich, bitch!”

Chappelle seemed shocked at the crowd’s reaction to Musk, who has fired numerous Twitter employees and has additionally angered many with fiery right-wing rhetoric.

Never one to choose silence at such an auspicious time, Chappelle told the crowd to “shut the f--- up,” and remarked that the boos were coming from the audience sitting in the arena’s “terrible seats.”

Perhaps all of these actions are Chappelle’s way of staying in the news. Comedians often court controversy as do other celebrities.

But Chappelle is one of the most famous, wealthiest, most controversial comedians if he never took another questionable step. He doesn’t need to engender controversy for publicity’s sake or any other reason.

He’s not some fledgling trying to make a name for himself.

He has as great a grasp on fame and success, and how to maintain them, as anyone alive.

We know he has a penchant for making interesting personal and business decisions. He walked away from a reported $50 million when he abandoned The Chappelle Show and fled overseas.

He may be fighting his own war against “wokeness,” much like his friend Musk. He might feel that he is fighting the good fight against censorship.

One wonders if Chappelle would embrace a fellow comedian who shared anti-Black tropes as quickly and easily as he does with anti-LGBTQ and anti-Jewish “jokes.”

Regardless of his reasons and rationale, Dave Chappelle isn’t walking a fine line with his humor and behavior, he has pole vaulted over any semblance of decency and decorum, and it doesn’t matter if it’s because he’s anointed himself a free speech warrior.

The transgendered comedian who defended Chappelle, Daphne Dorman, eventually committed suicide. She said of him,

“Punching down requires you to consider yourself superior to another group. Dave Chappelle doesn't consider himself better than me in any way. He isn't punching up or punching down. He's punching lines. That's his job and he's a master of his craft.”

Maybe Dave Chappelle doesn’t consider himself superior to LGBTQs, Jews, high school students, disadvantaged people, and Twitter layoffs.

But he has proven to be a master at punching down.