In our weekly series, we revisit some of our favorite music movies—from artist docs and concert films to biopics and fictional fantasies—that are available to stream or rent digitally. Spoilers ahead.
Like much of Brooklyn, the building formerly known as the Broken Angel was torn down a few years ago and resurrected as a multi-million-dollar condominium. Its previous residents, the artists Cynthia and Arthur Wood, had bought the one-time tenement for something like two grand in the 1970s, and gradually turned it into a living sculpture, 10 stories high. For decades, it towered over Clinton Hill to its west and Bed-Stuy to its east, beckoning fellow eccentrics with its stained-glass, cathedral-like construction.
In 2004, Dave Chappelle’s infamous street concert, documented in the 2006 film Dave Chappelle’s Block Party, boomed just under the shadow of the Broken Angel. He and director Michel Gondry included both the Woods and their building as secondary characters. “If I was a location scout and we needed a crack house, I might refer their place,” Chappelle joked to the camera. Within a decade of being immortalized in Block Party, Cynthia would be dead, Arthur evicted and exiled upstate, and the entire neighborhood transfigured.
Block Party is a concert film, and an overtly celebratory one at that. It cuts between portraits of attendees, preparations and rehearsals for the show, ad-hoc comedy bits, and rollicking performance footage from artists like the Roots, Yasiin Bey (fka Mos Def), and Talib Kweli. It’s imperfect, but ultimately an enjoyable and energizing watch—buoyed by an egalitarian balance of commentary from both beloved performers and unknown concertgoers. But gentrification, with its racialized contours, is a ghostly subplot hovering towards the edges of the frame. Though the documentary is often remembered as part of Chappelle’s first major comeback, it was shot months before he walked off the set of Chappelle’s Show, away from indignity and a $50 million contract, and into a sunset of his own devising. In other words, the Chappelle who bounds through Block Party is a comedian at his apex.
No one who appears in Block Party—not the people who are given golden tickets and a free trip to New York, not the college marching band recruited to soundtrack parts of the day, not the artists themselves—is as happy as Dave Chappelle. He swans, from Ohio to Brooklyn, with the calm irreverence of someone who knows he can have an idea and access to enough resources to execute it. The film masquerades as a vanity project, but it can more generously be interpreted as a statement of intent. Chappelle convened a brigade of artists whose music and careers were something of an analogue to his comedy: incisive, race-conscious, and improvisational. Most of those who joined him on-stage, including Erykah Badu, Jill Scott, and Common, had honed their sound on the incense-lit fringes of hip-hop and R&B, where music was a site of social responsibility, but, like Chappelle himself, became unlikely figures toward the forefront of American music.
Chappelle’s career has long intersected with music, drawing it close. There are similarities between the work, and sometimes even the temperament, of comics and musicians, as he notes in Block Party. Consider the parallels between the structure of an effective joke and that of an effective piece of music: the comedian and the artist are tasked with manipulating time and tension to carry an audience along with them, and to make the destination, be it a punchline or a hook, worth it. Nearly every episode of Chappelle’s Show featured a musical guest, and some of its most iconic sketches monumentalized artists like Prince and Rick James. During a brief Broadway run last summer, he selected musicians like Anderson .Paak and Thundercat, not comics, as his opening acts. At an after-party one night, in the basement of a hotel in Tribeca, he jammed with an impromptu band for hours, peaking with yet another cover of Radiohead’s “Creep.”
But a lot has changed, for Chappelle and for the rest of us, in the time between the block party and the after-party. As the Broken Angel was being reimagined as a gleaming emblem of gentrification, Chappelle was stripping himself for parts and forming his worldview, and his image, anew. He spent the years after Block Party in partial self-banishment, occasionally dipping his toes into stand-up and then retreating, often after sparring with audiences who bought tickets hoping to hear him regurgitate material from Chappelle’s Show. By 2017, a series of Netflix specials was overshadowed by his offensive and unfunny fixation on trans women and women’s issues revealed a different Chappelle, hardened and out of touch. The hero who left his star-making show because he felt some of his sketches skewed “socially irresponsible” had taken a willful turn, abandoning his responsibility to audiences.
Around the same time, Block Party performer Kanye West was embarking on a similar trajectory, turning his back on leftish politics in favor of a MAGA hat. There are clear differences between them—Chappelle is too smart to be pro-Trump—but the parallels are evident. As Rachel Kaadzi Ghansah pointed out in her all-time great Believer profile of Chappelle, there are uncanny biographical details that the two share, like their activist mothers and early introductions to radical black politics. Early on in their careers, they each became unelected middlemen, speaking to a country begging to be shaken out of its deluded, self-serving obsession with wealth and celebrity as the great racial equalizers. To reach those ends, both required a complicated relationship with their primarily white audiences.
About an hour into Block Party, Questlove breaks it down: “What we have in common is that our audience doesn’t look like us, and it’s the same for him,” he says, pointing to Chappelle. “The audience was full of these wild frat boys that just wanted him to do his character [from Half Baked]. When he was telling stories, they would always interrupt his narrative.” The complex push-and-pull between black performers and white audiences has been central dynamic in American popular culture over the past century, manifesting nightly in venues but also in the media. In the mid-’90s, Lauryn Hill, who headlined Block Party with a surprise reunion of the Fugees, was caught up in a mushrooming controversy. She was accused of having said that she’d rather die than have white fans buy her music. It wasn’t true, but it had seeds in a time-old, perennially relevant question about who makes the culture and who gets to wield their purchasing power in its face.
The block party of Block Party was Chappelle’s timid answer to that question. It was a proof-of-concept of a mostly black crowd, a kind of homegoing for he and fellow performers, a subtle commentary on racialized power dynamics at a time when such language hadn’t reached the mainstream. There’s a moment, when Erykah Badu flings off her wig, that suggests a kind of comfort I haven’t seen on many stages. Long before BBQ Beckys and Central Park Karens became etymological phenomenon, the block party as an event has been a site of racial conflict in cities around the country. Chappelle’s version may not have offered a replicable solution, but it was an act of political imagination he’s since abandoned. Watching him on-stage last summer, it seemed like he’s fully reversed course: the politically insensitive audience that once antagonized him is where he now mines his support.
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Originally Appeared on Pitchfork