There’s always a moment where you remember exactly when you stumbled upon genius.

Since 2000’s Killin’ Them Softly, I’ve been an advocate of Dave Chappelle and his humor. It was sixth grade and spouting off Chappelle wisdoms on race, voting, Sesame Street and more felt like a daily thing to do. It only supernova’d by the time I reached high school and by then, everyone walked around shouting “I’m Rick James, bitch!” and Chappelle’s own fame and talent cannibalized itself. In the three years that stretched in between Chappelle’s last HBO special and his Comedy Central show debuting, I’d grown up still holding on to the special, claiming Chappelle was the funniest man in America.

Every “hot” comedian has a streak where they’re the undisputed best. It was Pyror in the 70s, Eddie in the 80s, Chris Rock in the 90s and Dave had taken over. Sketch comedy shows for hot comedians was en vogue for a while. Almost like getting getting drafted straight out of high school and into the league for some. Some shows floundered but none prospered like Chappelle’s did – and none maintained their cultural relevancy afterwards either.


Out of the gate, Chappelle’s Show pretty much looked racism in its eye and decided to have a conversation with it. Most of its episodes dragged around the topic along with small hints of topical comedy here and there but nothing made Chappelle’s comedy seem funnier than his unique takes on racism. Spoofing HBO specials & reality shows were one thing, shrinking behind the immense talents of Wayne Brady and re-telling the days of Prince & Rick James running wild in the 80s via Charlie Murphy all worked in their own way.

But “Clayton Bigsby: Black White Supremacist”? Tops all of them for a number of reasons.

  • It closed the very first episode of the show and pretty much dictated whether or not the show would be a success or failure. “Popycopy” was somewhere in the middle and Dirty Vegas’ “Days Go By” for the Mitsubishi commercial where Dave’s yearning for titties kicked everything off.
  • Before Samuel L. Jackson made us hate him in Django Unchained and right around the same time Aaron McGruder was crafting Uncle Ruckus, Clayton Bigsby was the archtype for the self hating black man.
  • The flourishing use of the N-word and how we simply had to deal with it.
  • It’s Chappelle’s unabashed comedy version of Reasonable Doubt. The talent had always been bubbling on different circuits but this blew the doors off. Season 2 will always be appreciated more just because it really put Dave in a different realm, plus the twist on the concept of a white family with the last name “Niggar” is just too rich but to start off with this? Unreal.
  • At times I wish there was a documentary dedicated to Chappelle’s Show in the same way ESPN does 30 For 30. For a time, it legitimized Comedy Central and would routinely kick The Daily Show’s ass in the ratings. Plenty of shows from other comedians would come after it such as Carlos Mencia’s constantly baiting of race that wasn’t as funny, Daniel Tosh’s YouTube running show that MTV completely stole from him with Ridiculousness & Key & Peele on a tightrope of whether or not they’re funny or they’re funny.

    None of them can match the flame Chappelle set with his show – and nobody for that matter may do so ever.

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