9
by Geiginni
I have yet to see this special, but the last couple Netflix specials were pretty tired - where at least 85% of the material isn't new, or terribly insightful.
I think Chappelle is one of those guys whose core humor just doesn't age well. The freshness date is expired and there's no getting it back.
However he tries to portray himself as the oppressed minority when he's called out for his shitty positions on things, he's also someone who grew up in an environment of extreme privilege, economic and social. His parents were both academics and his upbringing was in a largely safe, well-to-do, suburban setting.
That last bit struck me as I was rewatching some of the first season of Chappelle's Show. A lot of that humor traded in the stock of stereotypes that were perhaps more commonly accepted at that time, and part of his comedic brilliance at that moment was turning those stereotypes inside-out in a way that seemed to attempt to take individuals in each community to task when their archetypical behavior aligned with those stereotypes - to their ultimate detriment (i.e. When Keeping It Real Goes Wrong). But, 20 years later, these things are not just tired, they're no longer relevant to the discussion or issues that continue to plague underprivileged populations.
One particular example that has aged poorly was the spoof of MTV's Real World where Dave pokes fun of the show's tendency to place one black guy in a house full of white people, and suppose what would happen if the tables were turned. When the tables are turned, it happens to be one white frat boy living in a house filled with a group of stereotypes that represent criminals, recidivists, poor work ethics, poor boundaries and poor personal and sexual ethics. Were these caricatures things he witnessed growing up in Silver Spring, or snippets of the stereotypes he witnessed when venturing out into the wider world away from his parent's ivory tower and their interactions with liberal celebrities?
I think part of the issue is his incapacity to 'punch-up' in his humor, and bring humorous insight to the issues of class, is that he is unapologetically part of the wealth class, has been part of that class for a long time and dare not impugn himself and his cohorts in that circle of privilege when it's much easier to use his race as an escape hatch when he gets called out for his reactionary opinions. This inability to check his own privilege when 'punching down' inevitably leads him in the direction of becoming essentially the "black Dennis Miller" - finding solace in a cadre of other "edgy" gen-x heteronormative males who are angry and just don't "get" the kids these days.