I think you're definitely on to something interesting. A certain type of clever humor is associated with exposing strange patterns that seem nonsensical or aren't examined, which for whatever strange reason we find funny. Wordplay is part of this as well (Scott Alexander has a whole book based on humorous wordplay, among other topics).
I would strongly suspect humor doesn't make you more rational/smarter/scientific, but is a fun grounds for playing around with strange ideas and patterns.
Having said that, I can think of worst ways to spend a Friday night :)
"I would strongly suspect humor doesn't make you more rational/smarter/scientific, but is a fun grounds for playing around with strange ideas and patterns."
Most humor (aside from physical comedy or a silly persona) seems to require deep verbal concept formation. Pointing out unexpected similarities based on the structures of ideas isn't cognitively trivial; it means that the comedian is able to extract essential features across superficially different subjects.
Well, stand-up comedy follows pretty much the scientific method: you come up with a routine, test it to the public, see what works and what doesn't, discard the second, come up with a new routine, and so on. Wash, rinse, repeat.
I don't know how much public there is for deep transhumanist humor, but robot stealing jobs to humans is a thing that started two centuries ago, so I would watch a comedian impersonating a robot stealing jobs from stupid humans, making fun of their most irrational traits.
Additionally, humor - especially self-effacing humor - allows one to critique ideas or people held in high esteem without being offensive or inciting anger. It's hard to be mad when you're laughing.
Thought: Humor lowers one's natural barriers to accepting new ideas.
In the context of ideas as memes that undergo Darwinian processes of mutation and natural selection, perhaps humor can be thought of as an immunodeficiency virus? A way to lower an idea's natural defenses against competing ideas, which is why we see Christians willing to listen to Atheist comics, and vice versa. Humor lowers Christianity's natural defenses against Atheism (group consolidation, faith, etc.) and allows new ideas to attack the weakened "body."
The theory of comedy that I find the most convincing is that things we find "funny" are non-threatening violations of social mores. According to that theory being funny isn't so much about being rational, but understanding the unwritten rules that govern society. More specifically it's about understanding when breaking social rules is actually acceptable. It's kind of like speeding. It's theoretically illegal to go 26 in a 25 mph zone. But as a practical matter, no cop is going to pull you over for it. I'm not sure that an especially detailed understanding of social norms is directly useful to becoming more rational. Maybe to the extent that you're more consciously aware of them and how they influence your thinking.
"Non-threatening violations of social mores" seems to underspecify what things are funny. Most non-threatening norm violations lead to other reactions like cringe, annoyance, sympathy, contempt, confusion, or indifference rather than comedy. Curb Your Enthusiasm and Mr. Bean had lots of funny scenes which involved norm violations, but if their creators were less talented then people would've cringed instead of laughing (and some people do that anyways). I don't think their talent consists primarily of 'finding ways to violate social mores' or 'figuring out how to make that benign'.
"Norm violations" and "non-threatening" also seem like generalizations that aren't true of all humor. "The crows seemed to be calling his name, thought Caw" and referencing movies don't seem like norm violations. Gallows humor and bullies laughing at their victim don't seem threat-free.
Epistemic status: Believed, but hard to know how much to adjust for opportunity costs
I'm wondering whether stand-up comedy would be a good way to expand and test one's "rationality skills" and/or just general interaction skills. One thing I like about it is that you get immediate feedback: the audience either laughs at your joke, or they don't.
Prominent existential risk researcher Nick Bostrom used to be a stand-up comedian:
For my postgraduate work, I went to London, where I studied physics and neuroscience at King's College, and obtained a PhD from the London School of Economics. For a while I did a little bit stand-up comedy on the vibrant London pub and theatre circuit.
It was also mentioned at the London LW meetup in June 2011:
Comedy as Anti-Compartmentalization - Another pet theory of mine. I was puzzled by the amount of atheist comedians out there, who people pay to see tell them that their religion is absurd. (Yes, Christian comedians exist too. Search YouTube. I dare you.) So my theory is that humour serves as a space where patterns and data from different fields are allowed to be superimposed on one another. Think of it as an anti-compartmentalization habit. Due to our brain design, compartmentalization is the default, so humour may be a hack to counter that. And we reward those who do it well with high status because it's valuable. Maybe we should have transhumanist/rationalist stand-up comedians? We sure have a lot of inconsistencies to point out.
Diego Caliero thinks that there would be good material to draw upon from the rationalist community.
Does anyone have any experience trying this and/or have thoughts on whether it would be useful? Also, does anyone in NYC want to try it out?