When Chappelle’s Show dropped in 2003, never in my history of comedic television viewing had a first episode been so explosive. Clayton Bigsby was the most audacious thing I’ve ever seen. A black white supremacist? I, along with millions of others, was hooked. Until then, Dave Chappelle was a marginal comic presence. He had bit roles in Robin Hood: Men in Tights, Blue Streak, Undercover Brother, and other films. Then he became a star with the stoners for the cult classic, 1998’s Half Baked. He was a stand-up whose career consisted of mostly juvenile and scatological humor with flashes of the socially and culturally relevant comedy displayed on the first two seasons of Chappelle’s Show. He was a hard worker. Dude toured and gave it his all. It was fascinating to see him mature from confident performer to a master of crowd control.

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Many people credit Eddie Murphy as being the first Hip-Hop comic. His swagger, boldness, impeccable timing — folks likened this to emceeing. To me, Murphy was the Bootsy Collins of comedy. He was never out the pocket, he was flamboyant, his rhythm was unimpeachable, and his charisma and charm were almost supernatural.

Dave Chappelle was the first hip-hop comic.

He bops. Even in a resting state, Chappelle is B-Boy’d out. Well, B-Boy by way of Bugs Bunny. He has the stance. He has the casual yet semi-threatening B-Boy about to battle walk. Despite his sometimes slow drawl, there is an energy coursing through Chappelle that is both freestyle cypher and Looney Tunes. His eyes and expressive face tell the story before the words do. We have the aura of the joke before the joke lands. And this is on stage. When he moved into the sketch comedy realm, he was transcendent.

The aforementioned Clayton Bigsby, his portrayals of Rick James and Prince (comedy gold as told by Charlie Murphy), the “Three Daves,” and the Training Day inspired sketch with Wayne Brady as the menacing Alonzo Harris character, Chappelle’s Show made the venerable Saturday Night Live look like a stack of discarded Yellow Pages.

There are still Chappelle’s Show sketches I watch and use when I teach, but some of them have not aged well. Others, I cannot stand.

I won’t get into the specific sketches that no longer work for me, but I feel about them the same way I feel about Dave Chappelle’s two new stand-up specials released this week on Netflix. Deep in the Heart of Texas: Dave Chappelle Live at Austin City Limits and The Age of Spin: Dave Chappelle Live at the Hollywood Palladium have generated so much buzz, both on and offline that I felt compelled to add my thoughts.

Some are hailing the specials as brilliant, while others are wondering if he lost a step. I find myself in the middle.

Granted, there are flashes of brilliance — a brilliance that stems from his ability to move the crowd and the supreme confidence of his stage presence. As soon as he steps from behind the screen, the audience and the stage is his. His stand up is more hip-hop concert than comedy performance. If you’re a performer of any kind, you need to watch Chappelle. Watching him is like watching an Olympic athlete. He is at the very top of the game, in terms of performance. But in regards to his jokes, I’m not so sure.

Many folks are talking about his trans/homophobic and rape content as deal breakers. He crossed the line with these and there is no going back. Some write off the trans/homophobic jokes as his operating from his own ignorance and that he’s actually poking fun at how much he doesn’t know. To me, th0se jokes came off as mean spirited.The rape jokes were lead balloons.

If you know me, you know that anyone can get it. I roast on any and all comers. I love a good cap. Hell, I’ve laughed at Black jokes that were funny. I was mad as hell afterwards, but if something is funny, it’s funny. But these jokes weren’t funny. I maybe would have laughed at them a few years ago, but now I can’t. It’s like listening to old hip-hop. When it first dropped, I was all in on Brand Nubian, Chubb Rock, N.W.A., all that. I listen to it now, and the anti-woman and anti-gay sentiments are just too much for me to enjoy the music.

Folks want to chalk this up to a new P.C. culture in entertainment. That comedians (in particular) are being hampered ++ that they aren’t allowed to say the unsayable anymore because of “special interest” groups. We’re all snowflakes who need safe spaces and trigger warnings.

I’d argue against this by pointing out that we are now in woke times and many no longer accept certain things to enter our spaces. We’ve erected social and cultural boundaries that have no space for misogyny or trans/homophobia. The funny thing is, most people are acting brand new. Like y’all didn’t recognize the problematic content before you climbed three spaces on the woke index.

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Dude has always had questionable politics. But we were without a decent comedic truth-teller for so long, we let him slide. He then did Dave Chappelle’s Block Party (one of my favorite movies) and we canonized him. We were all thirsty for that Murphy/Pryor/Carlin/Whoopie-In-Her-Prime that we embraced him, without question. Not to mention the B-Boy aesthetic of his show and stage performances put us over the top. If his stage performances opened the door, Chappelle’s Show cemented his legacy. But that was a long time ago.

Chappelle’s Show launched in 2003. It ended (if you count the 3rd season) in 2006. 11 years later, we’ve grown up. We have new sets of values. That’s what maturity is. He’s an absolutely stellar performer, but his material hasn’t matured with the times. He’s toured and has had as many hits as misses. But there has been many a hungry comedian who looked up to him, he studied his moves, and are now making moves of their own. They’ve occupied the space that Dave abandoned all those years ago. They’ve taken the anger and the edginess of Dave’s work, but have excised the misogyny and trans/homophobia. Dave will always be a legend. You have to give it up to him. There is no doubt that he is brilliant. What I’m wondering is if he’ll ever be contemporary again. But that’s just me.


This was a heated debate on Facebook. Folks were stating that for the $60 million dollar payday he received, he could do whatever he wanted. Don’t get that argument, but okay.

Someone came at me and stressed that I had “no idea what comedians do. You don’t know what it is like to be on stage, to feel the lights, to come up with material that the widest group of people found funny. F#&k you!!!”

I beg to differ. Peep below.

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