A half-hour into the Dave Chappelle show Thursday night at the Masonic, the crowd started yelling. They yelled that they loved him. They yelled to ask him to repeat lines from his old Comedy Central show. They yelled because they wanted to know what he thought of the homeless person who got sprayed with a hose in San Francisco earlier this year.

To his credit, Chappelle didn’t yell back. Instead, he engaged with the audience, part of his decadeslong dialogue with a city that he referred to during the show as his second home. He described playing hundreds of shows here earlier in his career — “using the city like a goddamn ATM” whenever he needed a paycheck. 

But it was clear his affection for the bay had run dry.

The type of audience back-and-forth he experienced Thursday night isn’t unprecedented at his San Francisco shows, and the feedback has had a large role in shaping his most controversial opinions. The late transgender comic Daphne Dorman confronted him during a performance at the Punch Line, which sparked a friendship between the comics. Dorman later died by suicide. Around the same time, Chappelle’s comedy took a dark turn toward transphobia: he identified as TERF (trans-exclusionary radical feminist), declared that gender is an unmalleable fact and insinuated that the struggle for LGBTQ and Black rights are at odds.

Chappelle didn’t go deep into his TERF beliefs Thursday; instead, he settled for a barrage of transphobic dog whistles. For those following his career closely, they drowned out everything else, but what was crystal clear was his disdain for present-day San Francisco. Chappelle, who was at the Warriors playoff game Wednesday, fondly recounted meeting Steph Curry as a rookie. And that was just about the only good thing he had to say about the city, at a show that was announced only two days earlier.

On his last visit to Chase Center, he brought Elon Musk onstage to a chorus of boos, and the time before that, a Hall of Fame’s worth of Bay Area rappers. At this event, there were no special guests. He didn’t mention Musk. Instead, he focused on the city’s homelessness problems. 

“What the f—k happened to this place?” he asked.

He told a story about eating at an Indian restaurant in the Tenderloin a few nights earlier, only to have someone defecate in front of the restaurant as he was walking in. San Francisco has become “half ‘Glee,’ half zombie movie,” he said, and he remarked that the whole city is the Tenderloin now. “Y’all [N-words] need a Batman!” he exclaimed. 

He wasn’t aware of the incident of a business owner hosing down a homeless person and had to have the crowd explain it. He pivoted quickly, saying he now remembered watching the video on YouTube … a hundred times. The misdirection was followed by a cruel snicker and a trademark slap of the mic against his thigh.

If you follow comedy or pop culture news, you know Chappelle has said plenty of irresponsible and dangerous things. Like Musk, Joe Rogan and Kanye West, he has insulated himself from criticism with a combination of incredible talent and incredible wealth. Nothing buttresses self-righteousness like being able to scream “I’m rich, bitch!” and mean it. But like with those other antagonists, Chappelle’s delusions get the best of him.

Chappelle didn’t repeat the “I’m rich, bitch” line from his TV show as an audience member requested; he said he wouldn’t do it because he doesn’t consider himself rich. That led another audience member to ask why he doesn’t think he’s rich, when he has purchased 20 pieces of property in his home of Yellow Springs, Ohio. In the set’s most eloquent moment, Chappelle responded that given the way Black people are treated in this country, no amount of money could make him feel rich.

BEST OF SFGATE


Most of the rest of the set was commentary on personal incidents that ended up in the news. Chappelle did an extended bit about being caught on camera at Floyd Mayweather’s strip club in Las Vegas and spoke about being attacked onstage at the Hollywood Bowl. A recent tour with Chris Rock led to a lengthy discussion of the Will Smith slap, and there was also a reference to criticism of antisemitic elements in his “Saturday Night Live” monologue.

But in the media, those incidents were all footnotes compared to the controversy over his comments on the transgender community. In addition to being insensitive, they are often just plain lazy, relying on tropes rather than the comedian’s incisive wit. At the Masonic, Chappelle noted that in his last special “The Closer,” he promised to stop making jokes about the LGBTQ community — then clarified that promise only applied to TV, punctuating the joke with another slap of the mic. 

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.

Controversial comedians these days often hide behind the defense that they’re just telling jokes, in the same way that disingenuous political commentators are “just asking questions.” I personally think that extraordinarily influential people like Chappelle should be held accountable for their words, especially if their job is literally just to get on stage and talk. But it was clear from the amount of laughter in the room — and his continual ability to sell out shows in the most LGBTQ+ friendly city in America — that there’s still a large portion of the population who will only ever know him as the guy that did those Rick James impressions. Those fans weren’t disappointed, but everyone else who has been paying attention would have been.

If you are in distress, call the Suicide & Crisis Lifeline 24 hours a day at 988, or visit 988lifeline.org for more resources.

More SF comedy reviews