The Tao of Physics, by Fritjof Capra
Dancing Wu Li Masters, by Gary Zukav
The Naked Ape, by Desmond Morris
The Road to Serfdom, by Friedrich Hayek
The Worldly Philosophers, by Robert Heilbroner
The Story of Philosophy, by Will Durant
Grammatical Man, by Jeremy Campbell
Zen and the Art of Motorcycle Maintenance, by Robert M. Pirsig
Flow, by Mihaly Csikszentmihalyi
Then I think that Grammatical Man and Penrose are around the nature of information, and what can be communicated and understood. And I sort of think that question is at the top of the tree of abstraction about what we think about. Then comes computer science and math which are about any symbolic systems or formal systems that can be computed and reasoned about. Then most everything else is applying those systems to various problems.
Then I think The Naked Ape and Hayek and Flow are around the notion that humans are their own thing. They are tribal and hierarchical and territorial and violent and not nearly as self-aware or even aware of our surroundings as we think we are. You get a lot more mileage out of just observing what they do than about listening to the rationalizations of why they say did it, things like God and blood and soil, i.e. superstitions and us-and-them-ing arbitrary physical features of a pack of mongrels and arbitrary lines on maps. Invitation to Sociology by Berger was another big one on those lines.
And the Heilbroner and Durant are basically inventories of major mental models that people have come up with in philosophy and economics.