I wouldn’t say it’s that clear cut. There’s no less Sorites Paradox in this demarcation than in most others. It’s not black and white, there can be fuzzy or grey areas, because there can be jokes that are unclear or come close to wrong outcomes in construct and thus are fuzzy as to where they fall on either metric, their humanity or axiomatic type (this was Chappelle’s concern with his faerie skit).

Moreover, there’s also humor in the idea that the Chappelle Show Brady, actually a dangerous psychopath, could so easily adapt to a profit-seeking system and take over Dave’s show. I think there’s a layer of the joke there that Chappelle is pointing out that thinking that some kind of underlying stereotypical blackness would somehow be transgressive or against systemic injustices is obviously false: a dangerous psychopathic gangster could potentially quite easily adapt to society.

In total, we’re supposed to eventually want the actual man Brady back because he was fun and genuine and a little corny.

(Also, Brady could himself let out some anger at having been pigeonholed by rhetorically giving Dave what he wanted).

This seems to be relevant to your distinction between Humor of the True and the False, where everyone knows which one is true (even if said hyperbolically) and which is false (even if said deadpan.) I’m not sure what everyone knows isn’t more a factoid than an identifiable thing. The actual discussion for me has the added difficulty I’ve never seen Chappelle or even heard of Tosh.

I always thought of comedy as conflict. The pun is a conflict of meanings, hence it is part of comedy. (I’m not altogether whether puns would be Humor of the True or the False, or possibly the highest form of humor, as it is both?) Aggression is one kind of conflict, hence the overlap of aggression and humor. The laugh is a defense against the conflict I suppose. The conflict between one’s own opinion of oneself and the reality is the heart of cringe comedy I guess, but then maybe that’s a resemblance to puns, both True and False?

In the theater, it is commonplace to say drama is conflict, but I disagree completely. The comedy is a conflict where there is a happy ending, the theatrical equivalent of the laugh. (Farces are comedies where the conflict has no consequences, tragicomedies or problem comedies take the consequences of conflict seriously and the great comedies are the ones where the audience truly believes in the resolution of the conflict.)