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 ci
