Getting complex jokes right would be impressive for me. I don't have much of a sense of aesthetic for music and most art. A painting looks good, but I don't understand how I'm supposed to appreciate. Half my music could be AI generated, and I wouldn't notice if it's background music. An AI generated wine would taste the same to me as a $1000 bottle. But I think most people understand comic genius. Chapelle's jokes are far better than someone who is on stage to deliver a performance with predictable material. You could probably apply this to all other art as well. A rap artist will recognize the genius of one artist vs another one who is cranking out junk. As with writing. As with music. I think we're still in that stage where we're impressed the AI can do anything at all.
You're right. Chappelle is controversial, and many rightfully abhor his material. However, I think you can look at the structure of his jokes objectively rather than the content. Obviously, you can't say all his material is like this. But the well paying shows are brilliant IMO. I appreciate his creativity compared to many other comics. Comedy is hard. That's why I said good comedy from bots is where I would really be impressed.