He had a magic ingredient in his early comedy which was the sense that he was completely unafraid of a crowd to the point where he was eager to court their discomfort and spite. On the extreme hostile end, this gave birth to such great moments as his rant against the heckling crowd in Philly. With a friendlier crowd, it enabled him to do routines on their sacred cows like feminism and female behaviour, while keeping them on-side with his down-to-earth dumbo schtick. The latter also gave the illusion that he was some kind of champion of common sense standards in an increasingly insane world, or that he was a pro-male voice or whatever...

In retrospect - and this realisation came to me at some point as a shower moment - all of this just comes from the fact that he's a deeply prideful, resentful, insecure guy, who likes the freedom to give one-sided rants on shit without anyone being able to blow him up for them. All his faux-dummy 'don't listen to me, I don't read books' type disclaimers in his acts are a folksy diversion because he secretly believes he's the smartest guy in any given room and hates when he gets any kind of pushback on a serious issue: see the 'let's not start this Joe' line in the vid, when Rogan asks a serious question about how far Burr wants to take covid masking. He seems constantly on the verge of weird vendettas or sulks with anyone who rubs him the wrong way or who applies pressure on his fragile worldview.

As he's gotten richer and more comfortable his perspectives have been more and more divorced from 'common' sense and his outlook has revolved more and more around validating his decision to marry a negress. It's easy to see why progressive delusions are increasingly seductive and comforting to such a guy, same as they're seductive to the average lefty - because he doesn't really believe in anything in the first place, and championing anti-racism or parroting the wokeshit of the month gives him a moral anchor and makes him feel like the good guy, the guy who made the right choices. And he parrots these things in the same tone that he used to deliver obvious scathing takedowns of feminist canards.

In short everything that used to make him funny was an act of compensation for a flawed personality. Now those same mannerisms highlight the flaws instead of cloaking them, and make him nauseating for me to watch or listen to.