Why you should care
Because Dave Chappelle’s razor-sharp wit can still stop you in your tracks.
If you are still reeling from the situations in Ferguson and Staten Island, allow Dave Chappelle to brighten your day with a piece of standup that is just as relevant today as it was over a decade ago. The year was 2000 and David Khari Webber Chappelle held court in Washington, D.C., for his first hour-long HBO special, Dave Chappelle: Killin’ Them Softly. Mind you, this was well before the sketch comedy phenomenon known as Chappelle’s Show swept the nation and turned Chappelle into a bona fide star — and his eventual departure after two and a half seasons due to the paranoia of success and the growing stress of maintaining his integrity, leaving an astounding $50 million deal from Comedy Central on the table.
This standup would serve as the foundation of what would eventually become his show. The subject is one that most black comedians have in their repertoire, but few deliver it with the panache of Chappelle. It combines a heavy-handed dose of truth serum about racial disparity when dealing with police, related through Chappelle’s outlandish, gut-busting storytelling.
He didn’t know he couldn’t race while intoxicated, with “We’re Not Gonna Take It” blasting from his car.
What makes this particular clip entertaining is the manner in which the jokes — delivered with Chappelle’s trademark nasal octave — never end with a simple punch line. Chappelle’s story about his drunk Caucasian friend Chip racing another car while Chappelle is in the passenger seat high on marijuana, unable to properly advise that this is the wrong thing to do, is one thing. But Chip’s drunken explanation to the officer that he didn’t know he couldn’t race another car while intoxicated, with Twisted Sister’s “We’re Not Gonna Take It” blasting from his car, is another. The hilarity crescendos as Chip tells Chappelle his excuse was great because “I did know I couldn’t do that,” with a wink and a grimace at the racial politics summed up in that one exchange.
When it comes to race relations, Chappelle has always been able to find the sweet spot between offensive and hilarious. As bizarre as his stories may be, there is a nugget of relatable reality here: Caucasians sympathize with the strained relationship between African Americans and police, while African Americans are happy to have their story told in a manner that doesn’t paint them as hapless victims.
But it’s this duality that haunted Chappelle as his star grew brighter. Mining his own culture for the benefit of a few laughs started to trouble him, and Chappelle grew increasingly wary of the truths in his comedy being lost while the jokes became little more than catchphrases obnoxiously shouted at him wherever he went. The question of whether fans were “laughing with me or at me” eventually led to Chappelle’s hiatus from comedy; as he’s explained in his triumphant return. But back when it was all so simple, Chappelle was at his finest. His ability to wrap the truth in hilarity and make the pill a little easier for his audiences to swallow has always made Chappelle a cut above the rest.
The complete hour special is available on HBO Go.