This is a place to consolidate book recommendations.
I'm reading The Logic of Failure and enjoying it quite a bit. I wasn't sure whether I'd heard of it here, and I found a post here called Great Books of Failure, an article which hadn't crossed my path before.
There's a recent thread about books for a gifted young teen and a slightly less recent discussion of books on cogsci thread which might or might not be found by someone looking for good books.
So, what books or lists of books do you recommend?
My picks, some of which have already been mentioned. I would classify these all as "viewquake" books for someone who hasn't encountered the concepts in them before.
Godel, Escher, Bach - gets a huge credit for sending me down the rabbit hole of "what your brain is actually doing", though like others I'm not sure if I would like it as much on a second reading.
Meditations by Marcus Aurelius - Stoicism at its best, I count this as the most motivational book I've ever read.
The Sciences of the Artificial by Herbert Simon - retreads topics that are probably already somewhat familiar to LW readers, but still has one of the highest insights/page ratios I've ever seen.
48 Laws of Power by Robert Greene - instrumental rationality in the social arena.
And one dis-recommendation:
I've only read bits and pieces of Godel, Escher, Bach but I certainly mean to read more. I'd borrow it from my parents, but my father (who showed me the Crab Canon when I was ten) is reading it to my fourteen year old little brother, and I'm certainly not about to interrupt! Maybe once I get around to paying back my library fees, yeah?