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The Brilliance of Dave Chappelle

Some call him the GOAT (including himself). Others label him the voice of his generation. He’s been called polarizing, divisive, transphobic, racist, and canceled. However, the appellation fans of comedy use most often are brilliant. That is a lofty and historically dangerous moniker for a stand-up comedian.

I once heard an audience member tell Eddie Griffin that he was a genius, and Griffin quickly said, “Don’t put that on me.” His reluctance for a title he might well have earned is fraught with pitfalls because once you’ve been anointed, you must continue to deliver at a level that leaves no room for quality diminishing criticism.

Talk about pressure. Being funny is hard enough, but being so all the time and more than your peers can be daunting as many an example of the crash and burn are fully documented and witnessed.

The first time I saw Dave Chappelle was at the Comedy Act Theater in Los Angeles. It was the early 90s, around the time of the untimely death of the club’s host, Robin Harris.

Fellow DC comedian David Edwards brought Dave in for a guest spot. He had yet to achieve any national recognition but was a hot commodity back East.

That night he delivered a solid but not overwhelmingly defining set. We deemed him a good comedian in a room full of good comedians. The Comedy Act Theater at the time was home to D L Hughley, Jamie Foxx, Joe Torry, TK Kirkland and Chris Tucker. 

dave chappelle
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The next time I saw Dave Chappelle, we worked together on the road, along with Ajai Sanders. The most memorable thing that struck me on that occasion was the size of Dave’s check (the promoter made a mistake and gave me Dave’s envelope). He was clocking big dollars long before his eventual notoriety, but Dave never flossed.

We did the show, then got high to the point of passing out (me). My next encounter with him was back in Hollywood at the Improv. He invited me outside to get me high and was driving a luxury vehicle most comics would’ve bragged on. When I asked Dave was it his he just smiled and passed the weed. 

I mention these personal experiences to illustrate the man behind the public persona or press. The Dave Chappelle I’ve encountered throughout the years is humble.

As a comedian, he does his job, has a good time doing it and like the late, great Prince, Dave would pop up at places after his own booked shows to get in one more set as well as entertain those in the community who might not have been able to afford his ticket price. Dave loves comedy and from there we can acknowledge what makes him brilliant.

Dave is a student of his craft. Chappelle knows his historical roots and his place in the arc known as stand-up comedy. He realizes to be effective in the lane he’s chosen requires a foundation of appreciation of the past and an understanding of here the art can go in the future.  

He has a curiosity and understanding of mankind.

Dave comes from an educated family. Scholars shaped his early development and his moral stance.

This is the reason Chappelle can incorporate relevant history into his routines as analogies or points of reference to his current topic. He has the comedic ability to look at trends and uses logic to predict the next step society might take.

The man is fearless. Chappelle knows that the worst that can happen to a comedian is a bomb. He’s had them like all comedians and survived.

With that understanding, he is able to say whatever he pleases without fear of being brought before a tribunal and put to death. He once said he speaks the language of funny fluently, and when you have that confidence in your abilities, you’re free to hold the mirror up to the masses and show them where we are VS where we’re being told we are.

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Dave makes the taboo relatable. Like Dick Gregory and Richard Pryor (his obvious forefathers), Chappelle broaches themes and subject matter that most comedians avoid.

Not because they are afraid of those topics, but because it takes a certain amount of comedy dexterity to navigate them and have an audience accept it. It’s one thing to bring it up but what are you saying about it that all walks of life can see your point. To shock or not to shock is the question many ask before structuring an act of even speaking. With Dave, that consideration is mute. 

Dave has a message. Chappelle gives you his worldview and his solutions and we accept them. We don’t have to like the brutal honesty of his presentation, but we do have to see where it comes from, and he gives us the roadmap of his thoughts. He’s rarely cryptic or vague. He let’s you in on the inner workings and why his way just might work for all of us.

One of his greatest attributes is how he’s so disarming. Few public personalities possess Chappelle’s elfin quality. Even fewer comedians outside of Ellen can make you feel this is innocence discovering what we all have taken for granted and learned to live with. It’s an amazing quality for a performer to have.

Despite his age and increased size, he is still at the core, that scrawny kid who said things off-handedly and meant no harm is saying it. So why are we tripping?

Dave has shown us he has integrity. In an industry populated with soul sellers, flip-floppers, and pure definitions of wishy-washy buck chasers, Chappelle has demonstrated he is a human of principle.

This might be his most important quality. We respected Muhammad Ali and recently Martha Stewart because they took their medicine and moved forward. Ali could’ve gone to the war and Stewart could’ve avoided jail time with countless appeals, but both stood up and showed us what they were made of as people. Dave did that when he walked away from a fortune. Who Dave is was more important to him than how much he earned.

He understands his era and is well aware that we live in a PC, sensitive time, but also in a cue-required mentality. We’re told what to do, how to think, what to buy, who to like and dislike. Society has gone from right seekers to puppets for the gatekeepers to keep off balance and profit from their confusion.

Chappelle knows this and uses this unfortunate state to woo us. Ever notice how he has a habit of hitting the microphone on his leg after a punchline?

This is relatively new for him. It’s a sign to the audience to laugh. An audience trained by a lifetime of laugh tracks. An audience who might’ve never been to a live comedy show, now knows what to laugh at Dave, which for Dave has to be more comfortable than feeling they didn’t get the jokes and supply him with the proper response. This way, whether they truly got it or not – they laughed in the right place.

Dave champions causes. All good humorists are known for something, but the great ones are known for something bigger than jokes or their style. Lenny Bruce championed freedom of speech. Dick Gregory – political understanding. Ellen – gay rights. In the case of Chappelle, it is our right to be ourselves. Not a coddler or one who panders, Chappelle hits everybody between the eyes with his truth, including himself. 

I think a true touch of brilliance is when Dave anointed himself. Katt Williams called him the GOAT and so have others so, why shouldn’t he? If people hear it or read it, more often than not they believe it. Is Dave Chapelle the GOAT (Greatest of all-time)? Only time will tell.