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Cats cradle, Kurt Vonnegut.
It wrecked me when I read it the first time, and it was the first time I experienced a writer ripping apart my brain and leaving me to jigsaw the thing back together.
A lot of his books could have done it, but that was the one that did.
https://www.goodreads.com/book/show/985613.Best_Loved_Folktales_of_the_World
Compiled by Joanna Cole
I have a lot of favorites for different criteria, but probably the easy answer that comes to mind is Hitchhiker's Guide to the Galaxy.
You sound like the kind of Hoopy Frood that knows where his towel is
Fiction: Jorge Luis Borges’ Ficciones
Non-fiction: Graeber and Wengrow’s The Dawn of Everything
My son caught me off guard asking me this question the other day. My first reply was The Stand, but there's a little book called Lying by Sam Harris that was pretty important to me.
Anyway, the reason I really replied was to say that many of John Grisham's books are kind of like candy, they just go down so quick. Fun reads by and large; The Partner is probably my favorite.
The Anatomy of Melancholy by Robert Burton
Came here to say H2G2 but somebody got it so I’ll go with The Nutmeg of Consolation
So far I’ve read 1984 5 times twice in school and 3 more times since graduation. The most recent was this past summer