The highest compliment you can give a philosopher is to explain in great detail why you think they are wrong. So thanks, Penguin. Unfortunately, I can’t return the compliment, because I think you are probably right.

If the previous paragraph is funny, I suppose it is because it violates common expectations. On the other hand, it could also be seen as self-inflicted cruelty, because I am falsifying my carefully written paper. My cruelty thesis was a simplification of two closely related theories: Henri Bergson’s “Comedy as rigidity” and Walter Kerr’s “Comedy as limitation”. This kind of theory assumes we must laugh AT the clown, because we see him/her as a buffoon or fool, or laugh AT whoever the clown is ridiculing. (Chris Rock is usually in the latter group, which is what got him into trouble). I think there is an essential place for such a clown, and I still stand behind my defense of Rock for performing this function. But I now think you’re right that comedy doesn’t have to be cruel. Sometimes it is just silly, and sometimes that silliness is inspired and profound. What you call subverted expectations is very similar to Douglas Hofstadter’s idea of “slippage”, and you can see that kind of inspired whimsy in books like his “Godel Escher Bach”. https://cogsci.indiana.edu/pub/hof+gabora.humor-workshop-1989.pdf

Your theory of Subverted expectations accounts for why silliness is funny and it also account for why cruel comedians are funny. That’s why we gasp and think “I can’t believe he said that!”.

The Rigidity/Limitation theory accounts for silliness by saying that it shows the mind breaking down. Our minds, instead of our bodies, slip on some kind of conceptual banana peel, and we slide off into absurdity. With someone like Robin Williams or Lord Buckley, we slip on this conceptual banana peel and sail off into space. But eventually what goes up does come down. One plausible theory for Robin William’s suicide was that he felt that he was going mad. His mind had gotten so good at sliding off the rails that it was harder and harder for him to get back on track again. Of course, there is nothing funny about a cruel twist of fate like Robin William’s suicide. But Kerr said that this fate is why comedy never really ends, It just ties things up with an arbitrary marriage or whatever so every one can ignore its only real natural ending: Our encounter with death, the ultimate limitation that hovers behind every joke we make.

And here my mind slips into a passage from a Woody Allen parody of Dostoyevsky.

I think my words must have touched my Uncle deeply, for he said “And you wonder why you are not invited to more parties. Jesus, you’re morbid.”