Chappelle’s Show is a strange hybrid. The cinematic clips uproot it from the live experience, but the recorded audience pulls it back down again. The big laughs are all things that a 2004 audience found funny or shocking. And some of them just aren’t that funny or shocking any more.
On top of this, so many of Chappelle’s sketches have become comedy classics that it’s hard to genuinely find them surprising anymore. “I’m Rick James, bitch!” was hilarious. Then your mom’s skeezy brother said it ten times at one holiday party a year after the show aired, and it didn’t feel so funny anymore.
Chappelle’s Show also gets bound up with what we know about Dave Chappelle’s history afterward. Dave famously quit the show because he felt that he was creatively tapped and was increasingly uncomfortable with the fact that jokes he’d intended as racial satire were getting laughed at for their silly, minstrelsy qualities. He even felt that his co-creators were complicit in this—he no longer felt comfortable working with them, so after recording several sketches for a much-anticipated third season, he briefly disappeared. There were rumors about his mental health and the possibility of drug abuse. Nobody could seem to grasp that somebody so successful didn’t like what he was doing anymore.