In February 2006, Dave Chappelle was interviewed by Oprah Whitney about walking off his eponymous Comedy Central sketch show.
The moment for him was when — while doing a sketch in blackface as a "visual personification of the N-word" — someone on the set laughed in a way that Chappelle read as laughing at him, rather than with him.
That made Chappelle reevaluate what he was doing, and if his comedy was sending the wrong message. Yet there was one other comment Chappelle made during that interview that really caught my ear.
In speaking about the way the entertainment industry disrespects Black entertainers, he said, "When I see that they put every Black man in the movies in a dress at some point in their career, I start connecting the dots."