Let us start with the following joke. "What do you think of this cartoon?" I asked.

This was the initial reply:
"I think the phrase 'CHECK, MATE!' is doing double duty: in chess, 'checkmate' is the familiar word meaning the king has been trapped and the game is over. In a restaurant, 'check' means the bill. So 'Check, mate!' can naturally mean, 'The bill, my friend'. The comma is what makes the interpretation possible."
"What do you think of the expression on the king?" I asked. The reply:
"The king's expression is actually the best part of the cartoon. He looks completely startled and alarmed—his eyes are wide, and he has the expression of someone who has suddenly realized that something might be seriously wrong. And that makes the joke work on another level.
Not at all bad. ChatGPT seems to have caught the joke comprehensively.
So I tried a slightly more complex chess cartoon. What did it think about this:

Its initial reaction:
"The gag is that chess pieces have invaded a tennis court. The court has been catastrophically cracked and damaged, while the pieces appear to be trying to deal with the aftermath. The piece on the right is apparently blaming himself. The joke is about the chess pieces behaving like people doing a job, while their chess identities remain relevant."
It didn't get the joke. So I asked it to "think of how bishops and rooks move." It's reply:
"Ah, yes. The movement of the chess pieces is the entire joke. I was missing the key clue. The two pieces are a bishop and a rook, and they're apparently trying to move the little box across the tennis court. The court has been cracked along the paths they've taken. The result is the bizarrely shattered tennis court we see in the picture."
"Actually they are drawing the lines of the tennis court" I prompted. Reaction:
That's exactly it! And that makes the cartoon much more elegant.
The bishop and rook are workers painting the lines of a tennis court. The little cart contains the paint, and the pieces are it to perform their work.
But they can only move according to the rules of chess: the bishop moves diagonally, so he has painted the diagonal lines, the rook moves horizontally or vertically, so he can paint the straight lines.
The poor bishop is therefore wrong for the job, and has painted a line in a direction that is useless for a tennis court.
So the fundamental joke is about what happens when you hire chess pieces to paint a tennis court. A rook is perfectly suited to the job; a bishop isn't.
I have lightly edited the above exchanges, which were longer and more convoluted.
In any case, discussing cartoons with AI is a lot of fun, and at the same time quite instructive. These systems, I believe, easily pass the Turing Test in this area of discussion.
Also read: Does AI understand humour?