You have suddenly help me finally piece together how Bob's humor "works." I'm going to break this into a kind of computer code since... well look at me. Anyway, just follow along, trust me.
Ok so we have the basic joke.
"Why did the chicken cross the road? To get to the other side."
We'll call this level 0. It's basically a joke with very minimum requirements. If you can understand the language, you can probably get it, even if you don't find it that funny.
Now we start to build on it.
"Why did the chicken cross the road? To show the opossum it could be done."
Now here we have level 1. This is where folks have taken the basic level 0 joke and begun to do variations on it. At least some part of the humor on this level depends on the joke existing in the first place.
Eventually you will vary it up even more.
"I want to live in a world where chickens can cross the road without having their motives questioned."
This is level 2. The entire humor of the joke is based upon the fact that the previous 2 levels exist below it and that the audience is familiar with the ubiquity of them to then see the humor in this. This is where we start getting into the meta level of humor where the joke is less about something specific and more about the existence of jokes themselves.
Obviously there's probably levels 3 and 4 out there too. (If you've had in-jokes for many years with VERY old friends, you'll probably notice this pattern repeating itself there)
Anyway, when you read some of Bob's tweets, you can almost trace exactly how Bob has some kind of vague awareness of this process and so tries to jump straight to a level 2 or 3 joke, without ever realizing that nobody around him are aware of level 0 and 1. I suspect this is mainly for 2 reasons: 1) He has no real theory of mind. 2) He knows making higher level jokes is something smart people do and he wants to appear smart.
So let's take this JD Vance thing and prove why Bob is so bad at humor.
Level 0 - Nobody likes JD Vance. They will ignore whatever he is trying to do.
Not much of a joke but it's his mind forming a baseline. Whether this is even true or not is also why Bob so often fails.
Level 1 - JD Vance drawing attention to something will have the opposite effect because people ignore him. Irony!
Building off the rudimentary base, you can start to see some vague resemblance to humor at this level.
Level 2 - The bad guys utilizing JD Vance to make people ignore the bad guys is just too wicked.
Right around here is where we start getting into the territory where Bob might tweet something. Instead of launching the basic jokes and building a lexicon and rapport with the audience, Bob has decided it is best to skip straight to the clever part and make the vague meta-allusions to the initial jokes and oh won't his audience laugh and think him so clever.
Because he never does realize that either 1) nobody is even on the same page that he's starting on, so he ends up looking insane or 2) they are in the vague ballpark and either don't agree or don't even find the foundations humorous.
Which has creepy implications that his few cult members either are the rare exceptions and do follow his train of thought - or like to pretend they do because then they get to seem clever because the youtube man seems clever.
Anyway thank you for coming to my TED talk.