The recursive one that I have actually been really liking recently, and I think is a real enough challenge is: "Answer the question 'What do you get when you cross a joke with a rhetorical question?'".
I append my own version of a chain-of-thought prompt, and I've gotten some responses that are quite satisfying and frankly enjoyable to read.
Here is an example of one such response in image form: https://imgur.com/a/Kgy1koi
It needs a bit more reasoning as it does find the answer but doesn't notice it found it.
The answer is: A trick question.
Yeah. In the example I shared, my charitable interpretation would be that it's identifying the trick question as "a setup" where the punch line is the confusion the audience experiences. And in a meta sense, that would also describe the form of the entire chat.
To state the obvious in case it wasn't: A trick question can be both a joke and a rhethorical question.