Dave Chappelle Can Always Be Like This

Dave Chappelle returned to host Saturday Night Live for the fourth time since 2016. He was humble, thoughtful, and very funny.

Dave Chappelle has hosted Saturday Night Live four times since his 2016 episode, but with the baggage that the legendary comic brings, it feels like more. An elder statesman at 51, he’s never anodyne. He’s more politically and socially slippery than people want him to be. When he first hosted the show — each of his episodes have come after important political events — Donald J. Trump was the President-elect for the first time, heading to the country’s most famous residence after defeating Hillary Clinton in a contentious campagin. “I will give Donald Trump a chance, and I will ask him that he gives us, the historically disenfranchised, a chance too”, Chappelle said in his 2016 episode, while smoking a cigarette. (The 2016 sketch with Chris Rock, where they’re amongst white friends who are surprised that Trump is winning is one of the very best sketches of the past ten years). It was a startlingly decent plea and sentiment in the face of anger and discontent. For a comedian known for his jokes on race and racism, the white power structure, mental illness, and how corporate structures stifle Black creativity, Chappelle was at ease, graceful, in a way that only time can allow a person to be. Lo and behold, Dave Chappelle, the wisdom-filled soothsayer, not the firebrand that he was at a younger age when the Chappelle Show was ruffling feathers with his thought-provoking but always hilarious sketches.

Saturday night, days before Donald Trump is set to become President again, Chappelle returned to the stage and was dynamite, calm, and concise. He tackled many subjects: the California fires, poor people, being a celebrity, Puff Daddy, Jimmy Carter, and the State of Isreal, apartheid, and Palestine. I was at a house party and we were on the edge of our seats, watching him like a preacher returning to his congregation after some time away. He’s captivating when he’s an oracle. He can be funny — the best thing you can be as a comic — instead of trying to get a rise out of people.

I would consider myself a Chappelle fan, and in my mind, his work will endure long after he leaves us, even though he’s definitely past his prime. Chappelle Show’s sketches were social commentary with laughter that expanded the vision of what comedy could be. Whether it was the Racial Draft, making fun of R. Kelly, or the “Black white supremacist” sketch, Chappelle directly observed structural and virtulent racism as America’s greatest sin, and race as the most defining feature of American life. (Chappelle is the descendant of William D. Chappelle, who was born a slave, then went on to be president at Allen University, a HBCU. W.D. Chappelle’s son, Dave’s grand-uncle, went on to open a small hospital in 1915 that provided care for Black Americans facing segregation in Columbia, South Carolina). To see him was to see him directly exposing dogmas that the Black community had relentlessly expressed before. It was honest, funny, and fearless; comedy at its zenith. However, his likability has taken a hit in the past ten years, as a hint of Black male conservatism has penetrated his comedy. In his sixth Netlfix special The Closer, Chappelle — and he’s done this too many times for me to count — spoke about his distrust of LGBTQ communities, more specifically, the trans community. He spoke about DaBaby being criticized for being homophobic but not for killing someone at a Walmart. He spoke about Caitlyn Jenner winning Woman of the Year after transitioning. He spoke about befriending Daphne Dorman, a trans comic who committed suicide. (Chappelle alleged that the online trans community harassed Dorman for being friends with him).

These words drew some ire towards Chappelle. You would be naive to think that it was just white liberals, too. They brought up facts about Chappelle, at this stage of his life: he was being paid handsomely by Netflix, to the tune of 20 million dollars per special. He was no longer a working class comedian who was bringing Mos Def and Kanye West to the national stage with him; he was a behemoth punching down towards a group of oppressed people. He wasn’t listening to trans people. He was making fun of trans people in the same way that the white men that Chappelle has always distrusted do. (A complicated thing about masculinity is how unifying it can be. That’s why Kanye West and Donald Trump seem to understand one another). Chappelle showed a lack of empathy, at times, for the troubles that trans people go through — particularly trans women, whose suicide rates are alarming. (Trans people are often subjected to a disproportionate amount of violence, too). It began to be frustrating watching him attack people who do not have a voice, when at his best, he gave a voice to the voiceless. For someone who knows how to discuss race so elegantly, it felt like he was actively being obtuse about trans people and their plight. On the flip side, ignoring or denouncing Chappelle’s controversial statements isn’t reckoning with some of the honest words that Chappelle has said over the years in his specials. “Being gay doesn’t mean you can’t be racist”, said Chappelle in The Closer, a true statement if you’ve ever met a white gay person. If race is the most defining feature of American life, and it still is, then it makes sense that Chappelle — one of America’s greatest thinkers on race — would have some quaalms about the whiteness that still exists in the LGBTQ community. How can one understand the complexities of identity without understanding race, first and foremost? How can Chappelle be as effective as a social commentator if he can’t acknowledge the unnerving statistics that the trans commmunity goes through? Everyone was at an impasse, not understanding one another’s thoughts, visibly ignoring everyone’s suffering.

The suffering of Black people is not always shared in other communities. Sure, they are Black gay people, but just because you found a few Black people that you can get down with doesn’t mean that you are someone who cares about Black people. (In the same way that is true, just because Chappelle had one trans friend doesn’t mean he cares about trans people). In history, the interests of white men and women quash the interests of Black men and women. This is what worries Chappelle when people express empathy for trans people and gay people. “What about racism?”, he wonders. He understands that the white power structure, Republican or Democrat, will forget about Black folks in the battle to win LGBTQ votes.

Chappelle is old enough, mature enough, to articulate himself better, though. He failed to do that. What is frustrating is that he did an excellent job of it in his opening monolgue. He showed a startling amount of humility. He talked about not knowing enough to know if Jimmy Carter was a great president. He talked about knowing Carter’s worth as a human being when Carter, who wrote a book called Palestine: Peace, not Apartheid, wasn’t afraid to come to the Middle East and speak to and empathize with Palestinians. He expressed that he wishes for Donald Trump to do better this time. “Remember, whether people voted for you or not, they’re all counting on you. Whether they like you or not, they’re all counting on you. The whole world is counting on you,” said Chappelle. “I mean this when I say this — good luck. Please do better next time. Please, all of us do better next time. Do not forget your humanity, and please have empathy for displaced people, whether they’re in the Palisades or Palestine.”

It had me wondering. What would his current reputation be like if he had chosen empathy more than he chose controversy?