I recently came across a passage that really resonated with me:
“…a lot of white people laughed at Dave Chappelle’s rapier racial satire for the wrong reasons, in ways that may have actually exacerbated stereotypes about black people in the minds of intellectual underachievers.”
The article referred to it as the “Chappelle’s Show conundrum” and concisely sums up my feelings about jokes around race. Basically no matter the intention or intelligence, the joke is interpreted by the audience member’s personal experience and bias.
And in the case of racial satire, it’s often taken in as the complete opposite of the intent. Instead of making fun of racism or educating the audience about a different race or a marginalized group, it ends up perpetuating those stereotypes it intends to make fun of.