Dave Chappelle kicked off his first weekend of the new year with a rare, riotous, nearly three-hour standup set at the Chapel in San Francisco, a city to which he admittedly owes a great deal.

The controversial comic famously logged hundreds of hours at the Punch Line comedy club after his departure from “Chappelle’s Show” in 2006, experiencing virtually every major milestone of the second act of his career through the unique lens of the city.

As brazen and unapologetic as ever, Chappelle was in rare form Saturday, Jan. 4, unconfined by tour schedules and standup specials, as evidenced by the two bottles of top-shelf Tequila, three packs of American Spirit cigarettes and one hefty joint — which he freely passed around to front row audience members — onstage throughout his extended act. The Ohio resident also covered a spectrum of topics, from God to Greta Thunberg.

Here’s the summation: Chappelle firmly believes in a perfect, all-knowing God, but not so much in a confident, climate-savvy teenager. Let’s just say the 17-year-old activist irks him, to put it mildly, rather than going into detail about Chappelle’s joke involving R. Kelly and Time magazine’s 2019 Person of the Year.

Even for a veteran comic like Chappelle, not every joke lands, and, given his uncompromising brand of humor, certain bits may come across as shockingly tone-deaf to certain Bay Area audience members. Such as Chappelle’s long-gestating, polarizing transgender jokes, which he spent another 30 minutes exploring without covering any new ground. Chappelle remains at an impasse on the issue — a stubborn, willful disconnect. He still doesn’t understand the concept of people shifting gender. He still thinks the trans experience is funny.

Despite his inability to understand something so fundamental, you get the sense that Chappelle has a profound respect for the trans community and the adversity they face. There’s a paradox in there somewhere.

Aside from a few gay slurs and customary racist jokes to supplement his trans material, Chappelle’s PC-averse material was outweighed by his thoughtful meditations on politics, pop culture, his career, personal life and existential musings.

The Democrat — although, unsurprisingly, Chappelle admits his popularity has risen among conservatives, with a MAGA audience member at a recent show demanding he run for president — said he might vote for Bernie Sanders if his face didn’t remind him of his Jewish accountant after he learned that Chappelle was broke in 2006.

Instead, Chappelle’s vote is with underdog Andrew Yang. Although he hasn’t publicly endorsed the candidate, Chappelle is performing at a benefit for him in the near future. The comedian joked that his past Chinese bits will come back to haunt him.

The more freely the Tequila flowed, the more Chappelle welcomed the audience’s questions. When asked whether he’d return to “Chappelle’s Show” if Netflix offered him the money, he replied with a blunt “No.” He went on to explain that, with Charlie Murphy dead and how things were left with Comedy Central, which aired the series, it wouldn’t be the same. It’s also a matter of principle, as Netflix isn’t the network that owes him money.

“I’m the type of person who doesn’t look back,” Chappelle said.

Perhaps that’s his defining characteristic: He doesn’t dwell on the past, lives in the present and remains hopeful of the future. He listed Ali Wong, Michelle Wolf and Tiffany Haddish as a few of his favorite female comedians, and, although “she’s great,” Mo’Nique as one of his least favorite due to her call for a Netflix boycott.

Chappelle also listed three of his all-time favorite shows in order from third to first: a recent Louis C.K. set in his home state, a Martin Lawrence set when he was 16 and a set in L.A. during the 1990s by a comic with cerebral palsy whose involuntary muscle movements disappeared as he brought the house down.

In between flirting with female audience members and theorizing about a gay attendee’s master plan to seduce his straight friend after the show, moments of profundity shined through, during which Chappelle got honest with himself and audience members about his own master plan: to live and let live. To forgive, appreciate and enjoy the intimate moments like the ones on Saturday night.

“It’s times like these that I know we’re all going to be all right,” he said.

Article via DateBook