Comedians like Dave Chapelle, Louis CK, Trey Parker & Matt Stone, Bill Burr, and many, many others, kick in every direction: up, down, left, right. Policing comedy with a lens of wokeness is a profoundly bad idea.

Chappelle has gotten a lot of stick for it lately if you haven’t noticed.

They all have, and the world is worse for it.

An anecdote: someone like Dave Chappelle is wildly popular on both the left and the right. Several friends of mine on the right devour his specials like a gourmet buffet. So when Chappelle gets up on stage and talks about his experiences with racism, police profiling, and inequality (as he did on yesterday's SNL monologue [0]), those same people on the right listen. They hear him. It moves the needle of justice forward by reaching an audience who otherwise wouldn't necessarily hear these stories.

[0]: https://youtu.be/Un_VvR_WqNs

This is not and has never been the "first rule of comedy". It's only very recently, since the scourge of wokeness, that people have been turning this shitty line. Comedy is comedy. Lots of different kinds of comedy can be funny. Stop trying to make it rigidly fit your world view.

Yup, first rule of comedy is, it's gotta be funny. That was Ken's actual sin here, and an apology should be all he needs to rectify it.

Depends on the purity of the laugh you're after. Obviously there are roasts, but if comedy had a score it'd be laughs and cheap shots always split the laughs with groans.

Having a rule like that is itself patronizing and demeaning, is it not?

Never listen to anyone making rules about comedy. Clearly they don't have any clue what they are talking about.

I'm not convinced that exclusively "kicking up" does anything to meaningfully solve intolerance

That's just something you made up. If you google for the first rule of comedy, the results I see are similar to "be funny", "surprise", "timing", etc.