The release of Dave Chappelle’s recent Netflix stand-up special “The Closer” has brought about much discussion on whether the comedian stepped over the line in continuing his long-running jokes centered around the LGBTQ community. Ultimately, Chappelle’s comedy is less about mockery of the group and is more rooted in jealousy since, in his eyes, they have been able to accomplish what the black community has not—mainstream acceptance. In this episode, I talk about the politics of comedy and the factors that have led to what Chappelle describes in his special. As is true with all of us, Dave Chappelle is a product of his environment and he exists at a time when states are passing laws requiring gender-neutral toy aisles while other states are passing laws geared at criminalizing black protest. He performs at a time when millions of dollars were spent fighting a Supreme Court case over a wedding cake, but at a time when the criminal justice system often lets down people of color. What are we to make of this dichotomy and is anyone to blame? I wrap up discussing how equality and progress should not be a zero-sum game, but that within the context of American history, it often is. Different groups of citizens are forced to “wait their turn” until the broader public and politicians are ready to accept them while they watch different groups quickly enter into mainstream culture and politics. Whether you find Chappelle’s special funny or not is a matter of comedic taste, but his politics, while at times uncomfortable, always makes us reflect and take stock of where we are as a nation.