San Francisco Reporter Angered by Dave Chappelle Telling the Truth About San Francisco

(Photo by Charles Sykes/Invision/AP, File)

While comedian Dave Chappelle’s familiarity with Biblical stories is unknown, one suspects that somewhere along the line, he heard the one about Daniel in the lion’s den and decided it would be a great business model. Why else would he do a show, with two days’ notice, in San Francisco? The event transpired on May 11 at the Masonic, an excellent venue featuring, among other amenities, comfortable seating. Alas, San Francisco Bay Area reporter Dan Gentile apparently found the only chair in the building not up to snuff, as all he got out of the evening was a massive case of butthurt.


Gentile’s review of Chappelle’s performance isn’t a review in the traditional sense. Rather, it contains near-endless variations on the same thing: how DARE you laugh with the nasty man!

True to his word, there were no extended segments about transgender people. Instead, he jabbed at the community over and over, slipping them into unrelated sections as a running punchline.

I’ll admit that Chappelle is a virtuosic storyteller, but I heard these dog whistles loud and clear, and it spoiled the set for me. However, I’m not sure how much of the audience really understood that context. For those that follow pop culture news, Chappelle’s transphobia has been one of the biggest stories of the past few years.

But at least one attendee at the show — the guy sitting next to me — admitted to barely knowing anything about Chappelle. My Lyft driver was also clueless about the controversy, and so were several other people I spoke to recently. They only knew that Chappelle is a really funny comedian, and in a way, this set proved that they’re not wrong. What’s so complicated about comedy — and almost everything — in the year 2023 is that my oblivious neighbor and I watched the show through completely different lenses.

In this context, “oblivious” translates into “why can’t you see that Chappelle is a MEANYPANTS!” The way Gentile carries on, you’d think Chappelle was wearing a MAKE AMERICA GREAT AGAIN hat. Or, perhaps Gentile is still stewing over Chappelle’s recent “Saturday Night Live” appearance.




The writer shoots himself in the foot early on when he mentions Chappelle’s friendship with transgender comedian Daphne Dorman. If someone is transphobic, being friends with a transgender person is a peculiar way of showing it. Also, if going transgender is the road to personal emancipation, why did Dorman commit suicide in 2019?

Gentile also whines about Chappelle being insensitive to the homeless. This attacking the messenger bit falls short, when one considers that—strange though it may seem—no known cases exist of anyone volunteering their domicile for a civilian reenactment of the Doctor Zhivago scene, in which the good doctor returns home after World War I’s conclusion only to discover said home was now governmentally decreed to be a squatters’ paradise.

In short, Gentile’s puerile screed is a litany of the usual complaints about how Chappelle is Mephistopheles incarnate for not bending a knee to the alphabet mafia. Also, words are violence, or something. Gentile uses this as an excuse to ignore Chappelle’s comments on San Francisco’s rotting (in some cases literally) condition. The only unlodged charge is Chappelle leaving the toilet seat up, although given his demonstrated knowledge of how things work, this is due to his expertise regarding which restroom to use.

There are two schools of comedy. One invents the absurd; a prime example of this is Monty Python. The other points out the obvious, such as wondering aloud why irons have a permanent press setting. Chappelle is a master of the latter. His job is not to mollycoddle the mirth-deficient or avoid goring someone else’s sacred cow. Chappelle will, at some point, make you angry. What you do with that anger is up to you. Do you rail against him for hurting your feeweeings, or do you enter into genuine self-reflection centered on whether he has exposed weakness, if not outright fallacy, in your belief system? Dave Chappelle is not the transgender community or homeless advocates’ worst enemy. They have themselves for that.



Editor’s Note: A previous version of this article indicated the show took place in March rather than May. We apologize to our readers for the error. 



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