I like critics, generally, though it definitely depends on the critic. I think the problem is in seeing critics of cultural media as a work of consumer advice or capital extraction. Media interpretation is inherently subjective and personal - no critic's interpretation is going to exactly mirror or represent your own, and aggregating a body of reactions and distilling them all into a simple up-down recommendation is inherently going to leave anybody dissatisfied. To me the purpose of consuming cultural analysis/criticism is to experience somebody else's perception of a piece of media and, hopefully, achieve a new framing of the piece of media which I hadn't previously considered - pretty much the same reason I consume media in the first place.
For example, the youtube channel **** Philosophy a few years back did a critique of Shrek analyzed through a Marxist framework. While the film certainly strains at times under such a monolithic and totalizing analysis, it was kind of a cool exercise, and led me to think about the film in a totally different light which I hadn't previously considered. Did it end with an up-down recommendation, or turn me into a frothing sycophant or hater of the film? No, not at all. But then, that, in my opinion, shouldn't be the point of criticism.
As for Chappelle - I haven't seen the new special, but from the sounds of it, it's of a kind with all of his past work. He's hilarious, insightful and incisive when he's criticizing black culture, or the white perception or interaction therewith, and is pretty awful in every other context. He's rightfully praised for his brilliant sketches like "Do You Know Black People" or "Frontline: Clayton Bigsby" or "The Mad Real World" or "The Racial Draft" or basically anything with Paul Mooney. But those represent a small subset of the sketches which appeared on The Chappelle's Show, and, at least in my opinion, as a comprehensive whole, the show had far more duds than people seem to remember.
As to a "good joke" about an oppressed community by someone not of that community, I think a good example would be George Carlin's bit on the economy of language in the context of how terminology regarding people suffering from PTSD has changed over the years. If you're going to make jokes at the expense of somebody else, the question needs to center on "what is being made fun of." From a structuralist perspective, the purpose of comedy is to identify an internalized contradiction in society and recontextualize in a way that makes that contradiction apparent and expose it such that the audience examines their own underlying base assumptions in a cathartic release. In this way, it follows this same thesis-antithesis-synthesis structure that all art - whether it be a play, a film, or a sonata follows. If you're telling a joke about an oppressed minority group and the punchline of the joke is simply "this person is different - isn't that funny?" or "all your cultural base assumptions about this minority group are true" - then that comic isn't really doing any of the work necessary to tell an effective joke - they're simply reifying the avenues of violence which keep that minority oppressed. They aren't challenging their audience, but rather confirming to that majority audience that it is ok for them to continue doing as they always have.
Carlin's bit is effective because it isn't punching down at people suffering from PTSD, but rather shining a light back at the majority audience. The joke isn't that "people with PTSD are broken isn't that funny?" but rather that, instead of doing anything to alleviate the suffering of people in need of help, we'd rather quibble about the correct terminology we use to refer to them and call it a day at that. Carlin is excoriating the people - many of whom are themselves in the audience - who might fancy themselves "woke" for using the "correct" terminology, but don't actually do the work of alleviating their suffering. It's an incisively identified contradiction - we as a society care enough about these people to police the terminology we use to refer to them, but not enough to actually do anything to help them. Rather, we use euphemistic language to shuffle them into a corner to make them go away, all the while donning the mantle of "a people who care." That's good comedy.
