When Dave Chappelle walked away from Chappelle’s Show after just three seasons, leaving a fifty million dollar deal on the table, he created a narrative. Prior to his abrupt two-week getaway to South Africa, Chappelle was more than just the man of the moment, his show was more than just the most popular on Comedy Central, arguably the most popular of all time and inarguably its most important. Chappelle was the mediator of an unprecedented cultural conversation about race, inequality, and deeply-sown institutional injustice. Every week, Chappelle and his troupe managed to sit an interracial audience in numbers that were outstanding for cable television and moderate a mature if hilarious conversation about the intricacies of cultural and institutional racism that pop culture had, until that point, largely avoided.

But after his disappearance, Chappelle became something of a comedy folk hero, his mythology spreading like an umbrella that threw a shadow over his countless moments of singular brilliance.  And, after stepping away, it would be nearly a decade before these issues were placed so nakedly in front of the eyes of the broad viewing public.

Luckily, a recent Netflix deal ensures a return of Chappelle, in the form of one newly-recorded stand-up special and two more never-before-seen specials from Chappelle’s stand-up vault.

In celebration of this forthcoming superstar resurrection, and as a reminder of why we would be well served to listen more closely this time, here are ten times that Dave Chappelle was right about everything.

Showbiz Sickness

This clip made the rounds last year through various media and social media outlets as a response to Kanye West’s exhaustion-fueled breakdown. Here, on Bravo’s Inside the Actor’s Studio, Dave discusses his experience with Martin Lawrence, his own struggles, and a similar breakdown by Mariah Carey to illustrate a point that is often forfeited by the general public’s insistence toward the easier narrative of the crazy, drugged out celebrity.

Police Brutality

This extended bit from Dave Chappelle’s HBO special Killin’ Them Softly is a hilarious illustration of the concept of white privilege drawn years before the longstanding phenomenon was given its spot-on descriptive buzzword, providing an opportunity to laugh at nod at the now-tragic truth that the institution of law enforcement has two different modes of operation: the advertised “protect and serve” goal for white Americans, and the unstated legal arm of oppression for non-white Americans.

How Old is Fifteen Really?

On his Showtime Special For What It’s Worth a few years later, Chappelle expounds upon the previous observation to discuss the role media plays in framing stories in ways that elevate white people and to control the narrative of non-white people, starting at a very young age.

The Difference Between 10 Million and Fifty Million Dollars

During his February 2015 interview on CBS’ Late Night with David Letterman, Chappelle discusses his abrupt departure from his show and his forfeiture of a small fortune. His quantification of his sacrifice and his own personally tortured misgivings about his decision to be, as he puts it, “seven years late for work,” introduce a consideration of the absurdity of the ceiling-less capitalist structure that allows for an illogical collection of capital but the difficulty of living in a world where value is measured not by capability, but by wealth and ownership.

Racist Animals

Though forgotten among some of the more legendary skits from his show, Chappelle’s fake Frontline report on the racism of animal TV stars, upon revisitation, lands as hard as the writer’s sharpest satire. The implication of the skit measures the roughly one generation gap between pre-Civil Rights era Hollywood and the Hollywood of the 2000s. When it’s pointed out that these theorized racist animal stars are no longer alive, it serves as a reminder that those who built oppressive structures prior to the Civil Right movement are not all gone, their work not entirely erased, and their attitudes preserved by the echoes of their efforts.

America Needs Discourse

In this clip from the aforementioned Inside the Actor’s Studio interview, Dave Chappelle explains to a young audience member who poses a question about America’s need to have an open discourse about race relations in a way that acknowledges the fixed structures. In a non-accusatory, measured tone, Dave lets the white male know of his position of privilege, his having benefited from these institutions, and leads a consideration in the culpability of that unknowing participation.

Two Americas

From For What It’s Worth, Chappelle talks bluntly about the two different Americas, about how our recollections of history communicate different messages to different citizens. His message goes further than to indict simple revisionist history, but to propose a sort of moral relativism to our nation’s beginnings, a relativism that might inspire those who were not descendants of its victims, but serve as an insult to those who still carry its wounds in their blood and heritage.

The N-Word

In Sundance’s Iconoclasts series, Dave Chappelle sat for a discussion with famed poet Maya Angelou, the two masters of separate forms building an intersection of perspective. At one point the conversation, which you can purchase on iTunes for $1.99, veers toward the responsibility of black Americans regarding their use of the N-word, to which a timid and clearly intimidated Chappelle offers the following:

There’s a particular rapper who’s a good friend of mine… This guy’s name is Mos Def, and we were having a conversation about that word in particular. Where it was initially used to dehumanize us, we adopted and speak of camaraderie with it. This is a mutual struggle — and he said — I know you’re gonna crush me in a minute, so I’m taking my time…  it used to be an exclusive word. That when they spoke that word about you, it would exclude you. And then he said what’s interesting now, that the culture of pendulum shifted so far the other way – where it’s cool to be black, that it’s exclusive the other way… Contrary to popular belief, in the core of who I am, I don’t think in terms of race. But I know that being a black man that I just have a very unique experience on the surface. People like Richard Pryor, or any artist, they can relate this experience of the black person, and then they see all these white people coming to their shows — and then the media will be like, “Well aren’t you surprised that so many white people like what you are saying?” No, because it’s a human experience.

Celebrity Opinions

Chappelle’s culture-condemning sequence toward the general population’s reaction to celebrities and their opinions on For What It’s Worth is exactly the kind of insightful commentary that might have come in handy over the last few years as we moved to elect a reality show star as the president.


And while we’re on the topic. It feels like forever ago when Dave Chappelle returned to the national stage at a pivotal moment as the host of NBC’s Saturday Night Live. As most reasonable Americans came to terms with the dread and confusion and disappointment, Chappelle’s opening monologue, full of his standard topical, personable, and reasoned comedy, was a welcome momentary escape. And if Trump’s first week of chaos has eliminated all that small dose comfort, we can only hope that Chappelle has more to say on the matter in his upcoming special. We could certainly use it. And we better listen this time.

Featured Image: NBC