Jelani Cobb’s Dave Chappelle & Dave Chappelle’s Robin Hood Feast

In 2007, Columbia University professor of Journalism and The New Yorker contributor, Jelani Cobb published a set of essays entitled,”The Devil & Dave Chappelle, & Other Essays”. In that collection’s eponymous essay, he writes of Dave Chappelle’s legendary departure from Comedy Central, leaving a highly touted $50 Million bag on that proverbial table. Comparing Dave Chappelle to Richard Pryor, he essentially hypothesizes that Dave Chappelle and Richard Pryor both transition from more “urban Black” forms of humor in front of Whyte audiences as a means of respecting that culture. In that essay, I highlight Cobbs’s pertinent sentiment concerning Richard Pryor and Dave Chappelle’s respective “conversions”:

Pryor told the New York Times Magazine in 1975, “I think there’s a thin line between being a Tom and [depicting] human beings. When I do the people, I have to do it true. If I can’t do it, I’ll stop right in the middle rather than pervert it and turn it into Tomism. There’s a thin line between to laugh with and to laugh at.” That line was at the forefront of Pryor’s mind when he returned from Africa in 1979. He renounced his use of the word “nigger,” later saying in his autobiography that it was “a wretched word. Its connotations weren’t funny even when people laughed…It was misunderstood by people. They didn’t get what I was talking about. Neither did I.”


Despite his later concerns, Pryor could get away with a skit like “Bicentennial Nigger,” in which a slave laughs about two centuries of bondage, rape, and lynching, because his 1976 audience understood the bitter indictment he was actually articulating. It would’ve been disastrous for the crossover Pryor of the 1980s to undertake that kind of sophisticated irony. The last skit Chappelle did before leaving the show was one in which a minidevil perches on people’s shoulders encouraging them to behave in stereotypical ways. In his case, the devil–who appears in blackface–convinces Chappelle’s character that he’ll be fulfilling a stereotype by ordering chicken on a flight. He dodges that trap by ordering fish, but the minstrel rejoices when learns it is catfish. The moral of the story is clear: Chappelle’s character lives in a catch-22 where anything he does fulfills some trait on an infinite checklist of stereotypes. It is a riff on the racial gymnastics required to negotiate the most routing of daily scenarios. Or it is a hilarious bit about a jigaboo dancing on an airplane. Depending upon who you’re talking to.

“The Devil & Dave Chappelle, & Other Essays”, William Jelani Cobb,
pg. 250-251

In May of 2017, Dave Chappelle performed at a charity gala for New York City’s Robin Hood. Robin Hood is an organization that bills itself as “Targeting Poverty In New York City”. While its website did not help me much in understanding their mission statement, they do claim that they “wrote the book on smart giving”. However, for our purposes here, Dave Chappelle’s comedic monologue is sufficient despite his audience’s somewhat mysterious identity.

I am including what appears to be a bulk of that routine’s video here.

Dave Chappelle Performing At Robin Hood Charity Gala May 2017

Dave Chappelle works in a world of narrative, satire, and stereotype. I consider one of Dave Chappelle’s comedic strengths his ability to include everyone in on a joke. Cobbs considers Richard and Dave’s work to be “inside jokes”, laughter aimed at others in an exclusive vernacular. I think differently. Dave Chappelle uses our othered counterparts as a mirror into our own ridiculous habits.

Take for example this routine’s introductory narration. Once again, mystery aside, but context matters. That is to say, his audience is a group of rich New York liberals that organize to end poverty in New York City. Dave Chappelle’s verbal skit, his narrative, is about a rich Black guy complaining about racism while living in luxury and spending exorbitantly while dodging a random homeless person. His story’s “moral” is a day of dealing with racism while enjoying shopping in upscale spaces and buying his homeless character a green velour Sean John outfit from Macy’s. He is not making fun of that homeless person; he is making fun of his audience via his own personage as narrator. “Making fun of” might be misinterpreted; I believe that metaphor of “holding a mirror up” to be a bit too self-righteous for Dave Chappelle’s brand, but it may work better to explain my thinking here.

I do not think Richard or Dave Chappelle need to be so tied to stories with morals. This can be shown somewhat by Dave’s own parenthetical to his audience about his story going “nowhere”. However, as Cobbs notes, I do believe both funny men exist in a “damn if you do, damn if you do not” paradox. In that paradox, they both work using humor in self-deprecating ways. Pryor’s is much more direct, highlighting his own infamous literal self-destruction with recreational substances. Chappelle mentioning that his homeless counterpart is also a Vietnam veteran borrows heavily from that same tradition of public self-ridicule as personal growth that Richard was so instrumental in defining.

In Dave Chappelle’s earlier work, he presented his viewing audience a series of skits entitled, “When Keeping It Real Goes Wrong.” These sketches had as premise a notion regarding consequences that might ensue when we attempt to abide by certain principles. Jelani Cobb interpreted this skit as:

The series “When Keeping It Real Goes Wrong” ridiculed the street ethics that have metastasized throughout black culture.

“The Devil & Dave Chappelle, & Other Essays”, William Jelani Cobb,
pg. 251

I think those sketches were more of a reflection of that comedic genius that wrote and performed them. Dave Chappelle is being self-deprecating,
and he invites us to share his personal inside joke. That joke being inside only in that we are also its butt. Dave Chappelle keeps it so real, that often it is difficult to be correct about where we think he has gone wrong.