I love Dave Chapelle’s work but this special was the only one I couldn’t finish, I just found it too cringy and unfunny. The topics he chose to make jokes about were not particularly nuanced and showed that he does not have much, if any, knowledge or experience in those topics. When Dave jokes about his experiences as a black man, he’s brilliant because he has in-depth knowledge and experience (as well as being well-read on the topic). The same goes for his experiences of fame and success. But when he makes jokes about Transgender people (for example), he’s just not funny because he does not know anything about the topic and so he misses any good material or viewpoints to be had.

But that’s not to say that humour can’t be found in the Transgender experience for example. The transgender youtuber Contra Points (Natalie Wyn) has said before that there is a lot of potentially funny material to be had from the transgender experience if a person knows about it or has personal experience with it. Dave Chappelle clearly does not, and seems unwilling to put the effort in to find the good, funny material in the topics he chose for this special.