Best of Whitlock: Dave Chappelle Hates Himself For Playing The ‘Black’ Role Assigned To Him By Bigots

As a present to OutKick’s loyal readers, we are proud to present some of Jason Whitlock’s best columns from 2020. Merry Christmas and Happy New Year. Enjoy!

For 16 minutes Saturday night, Dave Chappelle played Black in all the ways white liberals allow. Angry Black. Racist Black. Self-hating Black.

On the Saturday Night Live stage, the comedian joked and pontificated about a post-Trump America in a manner pleasing to the guilt-ridden white audience that surrounded him, and in a manner intended to venerate the defining characteristic white supremacists bestowed on us.


Four hundred years ago, American bigots relegated our skin color to a special distinction that limited our contribution to a civilized society. Four hundred years later, the ideological descendants of those bigots doubled-down on the distinction and the limitations, capitalizing the B in Black as a written reminder that dark skin is a defining characteristic above all else.

As we have been trained to do by our white liberal overseers and their social media apps, Dave Chappelle took the stage Saturday night determined to display a Hollywood-approved version of Blackness.

Mission accomplished. 

Chappelle sprinkled his rambling screed with the prerequisite use of the word “nigga.” He made racist generalizations about white people, including saying that the COVID pandemic had stopped white mass murderers and that white people who don’t like wearing masks are Klan members. 

Most important, Chappelle feigned disgust toward Donald Trump. Chappelle turned Trump’s brief battle with the coronavirus and Herman Cain’s death from it into a fable about Trump’s diabolical indifference to life.

“That’s your leader for four years!” Chappelle barked. “What kind of a man makes sure he’s OK while his friends fight for their lives and die? A white man.”

That white man sounds no different from the black men and women who say nothing as black children are slaughtered in the streets daily while passionately protesting the rare cases of a white police officer harming a black criminal suspect. 

Dave Chappelle knows this. Comedians used to gain fame for their ability and willingness to recognize and point out inconvenient truths. Intelligence and courage used to be requirements for humor. All that’s required now is a script. Chappelle stuck to the one NBC handed him.

Play black, with a capital B. Angry Black. Racist Black. Self-hating Black.

It’s a role that doesn’t fit Chappelle comfortably. His black skin is not his defining characteristic. He married an Asian woman. He lives in a white rural community. For a man of Chappelle’s station, marriage and zip code are choices, not conditions. Chappelle built his following cracking jokes for David Letterman, Conan O’Brien and Howard Stern. That’s not quite Arsenio Hall, Tyler Perry and Tom Joyner. 

When Chappelle isn’t on a stage straining to meet a liberal’s definition of Blackness, he lives a life that strains to meet the standard set by the great-grandfather he referenced at the top of his SNL monologue. According to his great-grandson, William David Chappelle, born a slave in South Carolina, spent his post-emancipation years pursuing three things: education, freedom for black people and Jesus Christ. That pursuit led him to meet with President Woodrow Wilson, who was considered sympathetic to the Confederacy. 

Chappelle’s great-granddaddy’s defining characteristic wasn’t his skin color. He took on the identity of a typical 19th century American, seeking and spreading knowledge, freedom and Christianity. 

It’s what we (black people) used to do before liberals re-imagined our purpose in life, before we self-imposed Black restrictions under the guise of 1970s Black pride associated with hairstyle, clothes and slang language.

Acting Black took precedence over acting smart, acting American or acting Christian. The tent poles of William David Chappelle’s existence were remade. Acting smart was acting white. The self-determination of freedom was cast as a racist, conservative plot to deny government assistance to black people. And Christianity was redefined as the primary tool of slavery, not the primary motivation of abolitionists.

No other American racial group lives under a restrictive burden of skin color. They are free to think, behave and believe as they see fit without threat of racial ostracization and recrimination. They’re free. Their skin color doesn’t define them. Four-hundred-year-old labels and limitations do not impede their pursuit of happiness. 

Offstage, Dave Chappelle is much like his great-grandfather. He is not ashamed of his black skin. He is, however, acutely aware of how little his skin color says about him. American white supremacists made skin color the center of Black identity, leaving knowledge, freedom and religious faith as the white man’s identifying characteristics.

We are Black. They — and everyone else — are Americans.

The last 60 years of American black-white racial history is not a mystery novel that can only be deciphered by the careful study of Ta-Nehisi Coates’ book, Shaun King’s racial justice campaigns and Jemele Hill’s tweets.

Bigots defined Blackness with a capital B, paid a handful of celebrities to model Black behavior and told the rest of us to act accordingly. We acquiesced. 

Dave Chappelle hates himself for going along with the plan.

A decade ago, after signing a $50 million contract to play his Black role, Chappelle ran away to Africa in shame. He’s been slowly working his way back into the good graces of his Hollywood handlers. Saturday night, he cleared another hurdle on his journey to redemption. With the world watching, he was given the assignment of instructing white people on how they should behave in post-Trump America.

He urged them to do random acts of kindness for undeserving black people. He said that a declining life expectancy brought on by heroin and suicide was causing angst and pain among white people. He said he knew that suffering. He claimed to know the frustration of police officers who feel targeted and unappreciated. And then he pivoted to draw the distinction he believes separates black people from white people.

“But here’s the difference between me and you,” he said. “You guys hate each other for that. And I don’t hate anybody. I just hate that feeling. That’s what I fight through. That’s what I suggest you fight through. You gotta find a way to live your life, find a way to forgive each other. You gotta find a way to find joy in your existence in spite of that feeling.

“And if you can’t do that, come get these nigga lessons.” 

He slammed the microphone to the ground, stared aimlessly at the floor and then lifted his head to acknowledge the sea of white, masked faces applauding his disjointed, racist and disingenuous diatribe.

Dave Chappelle is the bigoted white man’s favorite Black man. That’s why he still hates himself. To earn a living, he has to play Black in the ways liberals allow. Angry. Racist. Self-loathing. And obedient. 

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Written by Jason Whitlock

Jason Whitlock is a longtime sports writer, TV personality, radio host, podcaster and the newest member of the Outkick family.
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  1. I’m glad I wasn’t the only one that felt lost by his wandering thoughts while he seemed to make point and counterpoint with himself. He was pressured and uncomfortable. Thank you Jason for helping me see the reason. Chirp, chirp baby!

  2. Dave got some backlash in 2016 when he suggested that people give Trump a chance. He got hit hard by LGBTQ— for a special a couple years after that. He is the best comedian of his time but due the power of the woke elite will not earn a living by doing what he would naturally do. He is censored by the reality of the entertainment industry. I am willing to bet that he will be confronted with a choice of being woke compliant and being funny and will embrace his gift and just be funny. Ultimately the woke always eat their young and Dave is too be to be eaten.

  3. With the bigots in charge starting in January you fall in line or get canceled. It is race and only race 24/7. What kind of freedom is that? Hope Dave enjoys the money and approval of the bigots setting the conditions for him to be successful.

  4. Disagree a bit with your take on this one JW. While it fits in very well with your narrative over the last couple months (most of which are spot on / I think are brilliant…not with you on this one. Don’t know if you watched him recently on David Letterman’s series, or saw his impromptu long stand up after one of the more recent shootings (probably 2-3 months ago). His stand ups on Netflix were by no means sell outs. He does (negative) bits on both the 5 most common letters of the alphabet he wishes to roast, and in another doesn’t understand the T’s especially, pointing out a seeming contradiction in his own marital relationship. He also got +/- $100 million from Netflix for 2 or 3 stand up specials, and can name his price if he wants to tour. I feel he speaks HIS truth, and while it may be great fodder for your ongoing narrative, I don’t see him as a sellout.

      • Read it all. Big fan. Just referred to his “body of work” over the last year as opposed to one bit on SNL. Dave C is a bit bigger in pop culture, relevance, importance, and power than one 16 minute bit, whether one agrees with it or not. And thank you for not attacking me just for disagreeing with one thing on this site. One thing I love about Outkick!

        • I have also always been a fan of Chappelle. I didn’t really know what to make of his appearance on SNL. Chappelle seemed uncomfortable. Not his normal self. But after reading this column, Whitlock helped me make sense of my own thoughts.

          Did Chappelle speak “His truth”? I am not sure. I am sure Chappelle knows what it is like to experience racism. Because we all know racism exists. (and in my opinion, racism is being fueled more than ever by leftists who seem to want a race war). But does Chappelle really know what it’s like for Police officers with a target on their back? Does he know what it’s like for Officers in Portland who’ve had ball bearings shot at them, fireworks shot at them, rock solid bags of ice thrown at them? Does he know what it was like for the L.A. officer when she was shot in the face in an attempt to murder her? Does he know what these officers felt like when BLM protesters gathered outside their hospital (in a mostly peaceful protest) to scream that the pigs deserved to die? I am not sure Chappelle does know this experience.

          As for Chappelle’s shot at white men without compassion. Like Whitlock said: “That white man sounds no different from the black men and women who say nothing as black children are slaughtered in the streets daily while passionately protesting the rare cases of a white police officer harming a black criminal suspect.” We, as a society, have become too caught up in the political game. Compassion is something all too many of us lack, no matter our race.

          So I do agree with Whitlock. Whitlock helped me understand my own feelings on Chappelle’s speech. Whitlock also helped me understand why white liberals loved it so much. I think some of the white liberals I know might even try to squeeze in time for a random act of kindness, to stroke their own egos. They’ll see if they can squeeze it in between a couple of their Botox parties

  5. “A decade ago, after signing a $50 million contract to play his Black role, Chappelle ran away to Africa in shame. He’s been slowly working his way back into the good graces of his Hollywood handlers. Saturday night, he cleared another hurdle on his journey to redemption. With the world watching, he was given the assignment of instructing white people on how they should behave in post-Trump America.”

    “He slammed the microphone to the ground, stared aimlessly at the floor and then lifted his head to acknowledge the sea of white, masked faces applauding his disjointed, racist and disingenuous diatribe.”

    Wow. Just disheartening to see that he’s going back into those old doors, the same ones that caused him to disappear in the first place. In the words of Bunk Moreland: “Makes me sick, muthaf***a how far we done fell.”

  6. Related/ Unrelated. I, unapologetically live in Southern California in the affluent neighborhood of Del Mar. Unapologetically because I have a son who wishes to complete his education here in advance of me moving on. During the height of the recent BLM overtone, this neighborhood was so woke, you could feel the sun actually shining on their perfect heads. Every home had its own BLM sign and even some children got into the dance for undying support. They would gather at the corner, properly socially distanced, wave their signs, and have the cars honk in celebratory fashion. When all of the yard signs went up, so did the signs for their favorite politicians. They too were all the same. On just the one stretch of road to my home, there were 28 BLM signs in total. Today, after the elections have in their minds, ended, the signs for their favorite politicians are removed and along with them, the signs supporting BLM. There remain only 3 BLM signs as of last night, but they are also still surrounded by the signs of their favorite politicians.

    And my son ask why…

  7. What I don’t get is that Dave Chappell has “fuck you” money. A lot of B, C, D-list celebrities don’t have that luxury to say what they actually believe. Why would he need to appease Hollywood?

    Same with Kevin Hart. He got kicked off hosting some dumbass Hollywood circle-jerk award show for old tweets that were “homophobic”. Kevin Hart has the “fuck you” money as well. No need to apologize.

    • It isn’t just the money. The people that live in that part of society also have access to perks like you wouldn’t believe. I don’t know what Dave’s cup of tea is, but spending the weekend on their yacht, anchored off South Beach, with Jay-Z and Beyonce sure sounds nice, no? Or maybe take a flight to France for a few days at the chateau with Bono and a small group of Czech models? Or a comped dinner at the most exclusive restaurant in town, while you are in NYC for the show? Or your daughter’s birthday party at some tech billionaire’s ranch outside Taos?

      This doesn’t even begin to cover insider knowledge, access to investment opportunities, and who knows what els.

      This is why we get sold out constantly. It isn’t the money. Money scures a zip code and private schools. Everything else that comes along with selling out, is what makes life for these people, enviable.

      • AustinH, that is a good point. It is not just about the money. These elitists want to be part of the “club”. The want to be allowed to peak behind the curtain so to speak. They want to gain access to investments and who knows what else like you said. Great points. that is why we get sold out constantly. It is not an issue of race with our country but an issue of the elites in media and hollywood pitting us against ourselves.

      • Well said. Even though Chappelle apparently lives in the rural farmland of Ohio, I’m sure that he loves the privilege and access of getting on a private plane to jetset to wherever in the world with a you-name-it A-lister. For him, I guess it’s better to play the role and do as he is told than to be authentic. Sad.

  8. Its a shame Chappell bows to the racists, criminals, perverts and pedophiles of the Hollywood Hezbullah. Slicing these asswipes up and exposing them would be a great service to the average person. Being a sellout is being their puppet.
    The left does nothing but spew hate and division. Its how they keep their power by keeping racism alive and keeping all of their little sub groups hating each other.
    We need to lose the hyphens and just be Americans that belong to one race. Its called the human race.

  9. I used to watch the old Chappelle show on comedy central in the archives from the early 2000s and some of my favorite ones are where he plays basketball with prince and the one about Rick James and Charlie Murphy in a bar. That was the funny Dave Chappelle and now it seems he has caved to the leftists agenda. Such a talented comedian but now he has fallen. Love the analysis Mr. Whitlock.

  10. In 1975, boatloads of Vietnamese refugees hit the beach in California. They came from a country we’d all soon try to forget. They had no political benefactors, and there weren’t enough of them to do any political damage to an opposing party, so they were basically left on their own.
    Within months, families lived together, pooled their resources and began to work hard. They educated their children and started businesses. In very short order, they blew by Black America in income, home ownership, businesses and just about every other metric. Their story is what gives the LIE to “Racist America”.
    Black America sold out to the Left and Race hustlers, and now they reap the whirlwind.

  11. I recall Chris Rock saying that “woke” was the worst thing ever for comedians. It seemed there was nothing out of bounds for Eddie Murphy, Chris Rock, and Dave Chappelle in their younger days. Now, in order to stay in favor of the white liberals who run Hollywood and big tech along with the Twitter mob entertainers are asked to tow the line or risk their careers. The left destroys everything it touches…even comedy.

  12. For me work can be very demanding and I have to read a lot of uninteresting technical documents all day so I’m not often in the mood to read in my free time anymore but you are at the top of my list. I always look forward to your articles and I appreciate the videos too so I can listen in the car. You and Travis truly are fearless and it’s much appreciated.
    I’m a Dave Chapelle fan and I avoided the SNL monologue (and SNL period anymore) because I already knew what was coming. I ended up listening to most of it when you asked what people thought leading up to your article and for the most part it was as I expected. I don’t want to analyze it too much because it’s a comedy routine but he gets preachy on the topics of race and politics and I just think Dave is better then that. His jokes and insight were not outside the box like I would expect from him. It’s the same liberal Hollywood messaging that just misses home for me. We really have to stop grouping each other up by our races. It seems like an obvious thing but yet continues.

    Keep up the good work

  13. Hey Dave Chappelle…I get it…you’re between a rock and a hard place. So you gotta dig deep…really deep…and decide if you wanna be AN AMERICAN…or a Black…or a Black American (same as a black to most of us). WE WANT YOU TO BE AN AMERICAN…and join the brotherhood of the best place on Earth and the best experiment of human interaction ever conceived. You choose…continue to be a dickhead…or be a man. It ain’t toxic to be a man, it’s our destiny…to be one with those weird peeps from Venus that we have to put up with in order to survive and thrive!!!
    Throw off the yoke of the white libtards and grow some balls. We’d love to have you come over during the holidays with a six and some funny shit.

  14. Well done Whitlock! It’s about time somebody was analytical and critical of Chappelle. Btw, did anyone else notice Chappelle’s black privilege in that he’s been able to openly smoke cigarettes everywhere he performs? Who else can get away with that innn today’s age???

    The elite media falls all over itself in lauding Chappelle as a brave and fearless voice, but he’s been doing the same shuck-and-jive dance for damn near his entire career. Unlike Chris Rock, who can at least be occasionally critical of the black community, Chappelle is not much more than a funnier version of Louis Farrakhan in that EVERYTHING in America is the fault of whites and nothing will change until whites admit. I do also agree that there has to be some self-loathing in Chappelle in that he so often presents a ghetto version of black people in his standup and skits. The shame for doing so just for the sake of money has to be unbearable (hence his dependence on cigarettes and weed). Sad.

  15. I guess he was okay to say the n-word on national television? I guess since he was blasting Trump, it is okay for him to be uncensored. He has definitely taken the blue pill, but is choking on it a bit. Enjoy your money, and your sycophant lifestyle.

  16. i used to bragg that Dave was the funniest man alive. liberal lefty humor now includes non-funny jokes. his golden handcuffs are on now. he can’t turn away from the money and the attention. he used to be brilliant and an equal opportunity attack artist. i saw his first netflix special or one of them. can’t watch anymore. like jim carey, dave lost his humor in favor of the left mob.

  17. Great article. Not gonna lie though, I used to love some chapelle show. I didn’t take that as him playing the role that white liberals would like. I thought he was trying to push through PC and make us feel like it’s okay to joke about things with each other and bringing different races together.

  18. The book “SJW’s Always Lie” goes into people like the Asian married, white neighborhood living people like Dave Chappelle. He used to be edgy and funny – slaying sacred cows.

    Now he’s getting fitted for a dress, making sure the size is right. Sad!

  19. Jason Whitlock is one of my “go to” writers. His bio and mine are similar. My mother worked a small engine factory and cooked tuna noodle casseroles for her children after work. She did it because she had no options. Unlike Don Jr who learned how to cook a great soufflé from his father’s chef, in the pent house in the clouds. I grew up poor. I didn’t know I was poor, because everyone else was poor. We had shelter, food, and stability, so don’t feel sorry for me. It was rural and safe. It was an OK way to grow up. People had issues, some people dealt successfully with them, others didn’t. I understood those people, the problems they faced, and their attempt to work through those problems. I have never felt like I understood black people. It was not skin color based for me, maybe it was for the black folks I met, but not for me. Some black people would have nothing to do with me because I was white. Some black folks would have nothing to do with me because I was poor. What I learned from the black people who would associate with me was not complicated. I was sympathetic toward the black cause in college, until I learned black people did not want my sympathy. Black was Beautiful back then. Black folks wanted my respect. They wanted the same chance I had to enter middle class America. Work hard, succeed, start their families and pursue happiness. I will read this article several times. I think I understand black folks who are trying to work through their issues, just like I think I understand the white folks I grew up with, were trying to work through their issues. Thinking I understand people does not solve problems, but it is a start. Thank you Jason for your help. We are all trying to succeed. Some folks want to burn it all down. I am not one of them. I think burning it all down gives you ashes and nothing but a hole in the ground where dreams once lived. We are all Americans, we are not perfect Americans, but we are all in this together. God Bless America.

  20. Felt like I was getting lectured by another BLM actiivist…haven’t watched SNL in a long time but was always a Chappelle fan, his show was the funniest thing on the tube in the day, thought I’d give it a shot…And once again, Jason says it better than anyone…He hits more Home Runs than Bonds, Sosa, Maguire and the rest of the steroids crew combined..Be a VIP till they bury me cause you gotta search for the truth today and here it is…..every day

  21. Jason Haven ‘t watch SNL for years .But do like Chappelle I watch him on a couple comedy specials he tore up a lot of liberal stereotypes . I guess your saying he being rain in now the liberals are in charge again. Let us never forget. That White liberal and there thought police the blue check twitter mob the woke media along with Big tech and the Department of Justice a long with IRS .What White Liberal Hate the most is the First Amendment and people that speak there mines .And what threatens them the most is Black man who dares to be Free and think and say what he likes. Chappelle a very smart man he’s come back to the plantation before the destroy him.

  22. Great as usual Jason, and why Outkick will only continue to grow and grow.
    What you didn’t say specifically, but what I believe is the real undertone of what is being said, is that Chappelle, along with so many other ‘comedians’, no longer do comedy or funny social commentary. What they do now is simply straight up propaganda, and just one more part of the larger program, and one more well compensated useful idiot.

  23. All these wannabes stuck seem to be in a racialist loop. They are too young and missed the “Human Rights Movement” of the 50’s and 60’s and can’t move on and live in their own time and their own lives. Now that the Obamas have reappeared we are going to get a second helping of animus and division unless Trump can pull the election out and put these jackasses back in the barn.

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