Dave Chappelle just released a new comedy special streaming on Netflix called “The Dreamer,” and once again, San Francisco makes a major appearance. 

Chappelle has a long history in the city, becoming a regular at the Punch Line after he quit his Comedy Central show. Later in his career, he developed a friendship with the late trans comic Daphne Dorman, a San Francisco resident he has repeatedly invoked in his standup specials. He has drawn widespread condemnation from LGBTQ groups for transphobic comments.

The comic typically returns to San Francisco a few times a year (he once referred to the city as “an ATM machine” that he’d play whenever he needed money). When he comes to the city, controversy typically follows — at Chase Center in 2022 he brought out Elon Musk to boos, and at the Masonic he railed against the state of San Francisco. However, at his most recent appearance at the Punch Line in July 2023, he seemed to have moved past the type of culture war humor that tarnished his reputation among many fans.

Despite a proclamation at the end of his previous special “The Closer” that he was done telling jokes about the trans community, he continues to speak about LGBTQ people and gender identity throughout “The Dreamer.” The tone is less antagonistic, but the punchlines serve as clear dog whistles calling back to the previous controversy. Some jokes come across as lazy; at other moments Chappelle flashes his old brilliance. Whatever your thoughts are about Chappelle at this point, “The Dreamer” isn’t likely to change them.

Halfway through the set, Chappelle leaves the stage for a cigarette and returns to tell an extended story about San Francisco. At 22 years old, Chappelle was offered an HBO comedy special that was filmed at San Francisco’s Broadway Studios, located in North Beach. The venue was located above a nightclub, and 20 minutes into Chappelle’s set the club started playing loud music, which Chappelle thought ruined his show (although in the final product, the disruptive music isn’t audible). 

After that SF show, Chappelle kicked in the door to the production trailers outside the venue and started yelling at the staff. The producers blamed one of the people associated with the nightclub, so Chappelle turned his anger toward a man associated with the venue whom he identified as a Russian mobster. Chappelle ended up in the dark kitchen of the club cursing at the mobster, who blamed the producers. When Chappelle realized he was wrong, he apologized.

“It’s a funny thing if you believe you’re absolutely right. You can get drunk off the feeling of how right you are,” Chappelle says, before slipping in a punchline about gay people.

After apologizing to the mobster, Chappelle says, he had a realization in San Francisco that he explained in the final 10 minutes of his set. 

“In your life, at any given moment, the strongest dream in that moment wins that moment. I am a very powerful dreamer … 

“That’s the trick to life. You have to be wise enough to know when you are living in your dream. And you have to be humble enough to accept when you are in someone else’s.”