In 2006 I saw Dave Chappelle live at the Gotham Comedy Club. All I remember was that he had me dying of laughter for over an hour, and ended the set comparing capitalism to pimping. He’s brilliant. You cannot change my mind. 

His new Netflix special is actually two separate sets, filmed in two separate locations, at two separate periods of time. They each have their moments, but the first of the two is killer. 

A good friend of mine is a comedian, so I watch a lot of comedy, a lot of stand-up comedy. So how I watch a special is more for patterns and jokes, then just the jokes. I may not even laugh, and still enjoy it. 

Which brings me to the Age of Spin. Chappelle’s rhythm is brilliant. He’s a master at setting traps and his punchlines are unexpected. I was falling over with laughter and amazed at what he was doing. 

What is so brilliant is his honesty about his discomfort in a changing world. His desire to respect everyone’s right to be who they are, while clinging to what he’s grown accustomed to. His active engagement with these dueling forces is evident throughout the special, as well as the second special Live at Austin City Limits

Because these days we exist in the Woke Olympics, everyone is dying to be woker than the next person. And lost in that is active engagement. Yes it is wrong to discriminate against people in protected classes. But why? 

For Chappelle to allow viewers into his own quest to find his why is BOLD. It’s hella courageous and I suspect is at the heart of the critique many have of the special. But for me, I loved it. 

I am hella woke on many things. And I too am actively wrestling with others. It’s part of why I write. I don’t speak on things I haven’t fully thought through. But maybe I should.

Wokeness is a constant journey of awakening. It isn’t a moment that happens and in that moment you have arrived. To truly be committed to “the struggle”, or whatever, requires a constant learning and unlearning, a constant inquiry, an unending process of becoming. 

I’m grateful for the window into Chappelle’s process. I’m also grateful for those jokes.