Elon Musk cameo exemplifies issues at Dave Chappelle, Chris Rock SF show

While it was the biggest talking point of Sunday night’s San Francisco show, Dave Chappelle bringing out Elon Musk was just one example of Chappelle and co-headliner Chris Rock challenging the Chase Center audience.

Throughout the night, the comedians railed against supposed “safe spaces,” even as they discussed everything from the Ukraine war to the Oscars to Bay Area homelessness. The two comedians just couldn’t stop taking shots — veiled and unveiled — at their idea of cancel culture.

Chappelle and Rock still know how to get a laugh. The Chase Center was positively shaking at points, with audience members gasping for air from all the cry-laughing. They didn’t become two of the most successful comedians of their generation without bearing unbelievable amounts of wit, timing and courage. Despite the fact that they’re both more than 30 years into their careers, they remain as sharp as ever, especially during live performances.

But where they stumble is in their fixation on cancel culture. From the opening acts (Rick Ingraham and Chappelle show alum Donnell Rawlings) to the legendary headliners themselves, the performers seemed preoccupied with “wokeness.” Ingraham and Rawlings made fun of the supposedly fragile Gen Z, whom they knocked for technology addictions and voicing their opinions on TikTok. Chappelle and Rock, meanwhile, consistently complained about the perceived ceaseless victimhood they see in the world.

The act felt a bit tired at this point. First of all, it’s hard to pretend that either Rock or Chappelle are in danger of being canceled, with the cheapest seats for Sunday reselling at nearly $300 apiece. They’re railing against what they perceive as negative consequences for telling hard truths, but the reality is, between sell-out audiences and huge TV deals, they’re not facing many consequences at all.

For his part, Rock based his act on the idea that “selective outrage” was to blame for many of America’s ills and that Americans need to toughen up against perceived slights.

“Anyone who says words hurt has never been punched in the face,” said Rock, referencing his infamous clash with Will Smith at the 2022 Oscars.

Rock also called out performative activism at the corporate and personal level. He joked that every single house in his all-white neighborhood has a Black Lives Matter sign up (“I had to put a Trump sign up to keep up the property values,” he quipped), and about the hypocrisy of Lululemon charging exorbitant prices while claiming to be against hate. (“They sell $100 yoga pants, they hate somebody,” he said.)

Chappelle, who took the stage last, appeared prepared to buck the trend of anti-woke grumblings. For the most part, he stayed away from his most controversial material, seeming less interested in examining his hurtful transphobic and antisemitic comments, which have tarnished the comedian’s once-stellar reputation.

Instead, Chappelle focused on traditional comedy subjects like sex, drugs and fame. He also tailored his routine to his Bay Area audience, ribbing San Francisco about homelessness, the Tenderloin and the amount of software developers in attendance. He even managed to name-check Harvey Milk, joking that if he were to portray the San Francisco city councilmember in a biopic, it would have to be called “Chocolate Milk.”

Unfortunately, he could not fully avoid jokes at the expense of transgender and Jewish people. In reference to an incident a few months ago when he was rushed and tackled onstage, Chappelle said he felt confident the person was not a queer activist.  

“Everyone I meet from the [LGBTQI] community is so nice to me in person. There is no way one of them did that to me. It must have been the Jews,” said Chappelle, doubling down on his recent “Saturday Night Live” monologue, which was called out for repeating antisemitic tropes. He also joked that his attacker was armed with a “knife that identified as a gun,” making light of trans identity.

Chappelle’s desire to shock, reaffirmed by his choice to bring out Musk, gets in the way of his act. It’s too bad, because Chappelle is still undeniably one of the funniest people on the planet when he’s not taking cheap shots. His confidence onstage is unparalleled, and he seems to be making up half of his hilarious stories in real-time, which is a testament to his gift for storytelling and the decades he’s spent honing his craft.

Indeed, some of the funniest parts of the show took place when he was improvising. In one side-splitting moment, he pointed to a father and son duo in the audience and bluffed like he was going to say something meaningful about fatherhood, only to remind the teenage son that his father also masturbates. It’s this kind of comedy, which skewers the extreme human-ness of us all, where Chappelle shines. 

But by taking aim at marginalized communities and people who face harm for their identities, Chappelle has started to chip away at the goodwill he has built through his generational talent. And when Elon Musk took the stage, a little more of it was lost.