Fiction:
Herman Hesse - Siddhartha, Damian, The Glass Bead Game (also called Magister Ludi).
All three are philosophical fiction. Strong eastern influence, but they cover a lot of ground.
Siddhartha is about the philosophical and spiritual development of the first buddha, I don’t know how historical it is but it present a lot of different strains of buddhist philosophy pretty well.
Damian is similarly a novel about philosophical development. More western philosophical influence, lots about the nature of good and evil.
The Glass Bead Game is an allegorical autobiography, so again about philosophical development and institutional learning. A good critique of the ivory tower.
For context, I didn’t like Hesse’s Steppenwolf.
John le Carre - A Perfect Spy, The Night Manager, The Spy Who Came In From the Cold
Spy fiction, but well written.
The Night Manager is pulpier than the other two, about a night manager in a hotel who gets caught up in an arms deal.
The Spy Who Came In From the Cold is about the cold war, cynical but good depth.
A Perfect Spy is the most abstract, lots of spy elements but also good rumination on trust and lies and duty and family and love and what have you. It’s a little stream-of-consciousness, it was a sort of emotional catharsis for le Carre and he wrote it in a very short period of time, but it is still be my favorite of his works.
I’ve loved everything I’ve read by le Carre, but these are my top three.
Orson Scott Card - Ender’s Game
Fuck the dude for his politics, but goddamned if this isn’t a phenomenal book. Sci-fi bildungsroman. I recommend pirating it, because seriously, fuck that dude.
Non-fiction:
Niall Ferguson - The Ascent of Money
Great book about where money came from and what it means and how we should think about it. I read this in the dying days of my communist streak, so it might have been partly the right-book-at-the-right-time effect, but it is well researched and engagingly written.
David Brin - The Transparent Society
Brin is a sci-fi writer, but this book is non-fiction. Here he argues that the best way to protect ourselves from the specter of the surveillance state is to open up the surveillance state, and society as a whole, to what he calls sousveillance (‘sur’ meaning ‘above’, ‘sous’ meaning ‘below’. See what he did there?). He’s basically defending the social panopticon by expanding it to include the jailers as well as the prisoners. Excellent and challenging.
Douglas Hofstadter - Godel, Escher, Bach
So well done. Hofstadter is an honest to goodness genius, and it shows in this book that presents ideas on so many levels at once. It’s hard to describe, but it’s basically building an argument from math up to consciousness through music and biology and poetry. Chapters are interspersed with socratic-like dialogues that are sometimes absurd, but illustrate the ideas being discussed.
Jay MacLoed - Ain’t No Makin’ It
A book about poverty and inequality, based on an in depth investigation into the lives of kids growing up in a housing project. The book follows them through their lives. It’s emotionally hard to read, but it’s engrossing. For context, I grew up relatively well off not far from where this book was written, so it could be that it’s interestingness is particular to my background.