Fascinating list!

Your point about Chesterton's Orthodoxy and how you have to look stuff up reminds me of author Helene Hanff--a writer who grew up too poor to go to college. So she went to the library instead and read all she could, and when she came across stuff she didn't know about, she would tell her current book "wait here!" and go read what she needed to catch, then go back to the original book. She details that in her memoir "Q's Legacy," but her famous book is "84, Charing Cross Road." Those might be fun reads if you haven't come across them yet.

NN Taleb kind of lives in a different world than the rest of us, I think, so I don't know that his idea of hilarious and mine would line up. :)

Loved The Secret History and Handmaid's Tale! Haven't read the others--I don't read a lot of fiction. But may look into "Normal People" because now I'm curious.