What have been the most influential books which increase awareness and/or understanding of how the world operates?

 The Selfish Gene - Richard Dawkins


Here's a list of books I've come across that fit this bill in my own idiosyncratic areas of interest:

International conflict

• Man, the State, and War by Kenneth Waltz
• Theory of International Politics by Kenneth Waltz. Waltz is arguably the greatest mind in international relations in our lifetime. These are two amazing books about how international relations really work. Absolutely required reading.
• History of the Peloponnesian War by Thucydides. Other than Waltz, the other book to read.
• The Gathering Storm: first volume of Winston Churchill's WWII memoirs. This book is awesome.

Non-US cultures

• Born Red: A Chronicle of the Cultural Revolution. Wow this is an amazingly insightful story of the Cultural Revolution, told first hand.
• From Beirut to Jerusalem by Tom Friedman: This book is a little out of date now, but an incredible overview of Middle East history and cultural conflicts. One of my favorite 100 books.

American politics

• Presidential Power by Richard Neustadt. Amazing overview of White House politics.
• Congress: The Electoral Connection by David Mayhew.
• Congress and The Bureaucracy by Douglas Arnold.
• The Brethren by Bob Woodward. Great Supreme Court overview.
• Federalist Papers. Very readable (surprisingly). Great recap of all the big issues behind the making of the U.S. Constitution.

Game theory and economics

• Strategy of Conflict by Thomas Schelling. My favorite overview of game theory. Has lots of practical examples.
• A Course in Microeconomic Theory by David Kreps. Not easy for non-economists, but good.

Other

• Real and Functional Analysis by Serge Lang. If you're trying to understand analysis, this is pretty great.
• A First Course in Probability by Sheldon Ross.
• Stickney and Weil: Financial Accounting. Really lucid overview of accounting. You can teach yourself with this book.

Most of these topics (Middle East politics, Cultural Revolution, real analysis, accounting) are about fields/topics which are really difficult to grasp as a beginner. Each of these books put a giant smile on my face re: illuminating a black box that I cared about.


 Wow, what a great question!  It suddenly occurs to me that I've spent the last ten years of my life answering just this question...

I've found the following books particularly useful in trying to understand the world.  (And I'm an independent teacher, so I get to talk about many of these books all the time — I live a good life!)

Starred (*) books are my very favorites.


HUMAN HISTORY
What are the broad strokes of cosmic / human history?

• The Cartoon History of the Universe I, II, and III, and The Cartoon History of the Modern World I and II, by Larry Gonick.
• Big History: The Big Bang, Life on Earth, and the Rise of Humanity, by David Christian (Great Courses DVD series).

Why did Europeans conquer the world?

• Guns, Germs, and Steel: The Fates of Human Societies, by Jared Diamond.

Why did Abrahamic monotheism conquer the world?

• The Rise of Christianity: How the Obscure, Marginal Jesus Movement Became the Dominant Religious Force in the Western World in a Few Centuries, by Rodney Stark, or
• The Triumph of Christianity: How the Jesus Movement Became the World's Largest Religion, by the same.
• The Evolution of God, by Robert Wright.
• Paul among the People: The Apostle Reinterpreted and Reimagined in His Own Time, by Sarah Ruden.

(My apologies that all of these but Wright's book concern Christianity exclusively.)

Is modernity good for us?

• The World Until Yesterday: What Can We Learn from Traditional Societies? by Jared Diamond.

What is "marriage"? Where did it come from? Where is it going?

• Marriage, A History: How Love Conquered Marriage, by Stephanie Coontz.

How should we see America?

• A People's History of the United States by Howard Zinn AND
• A History of the American People by Paul Johnson.

(Zinn is a radical of the Left, and Johnson of the Right. These books really need to be read next to each other — I had read them both independently, but it wasn't until I taught a class that used them both together that I saw how obscenely silly both perspectives could be at points.)

Why did al-Qaeda strike on 9/11?

• Imperial Hubris: Why the West is Losing the War on Terror, by Michael Scheuer.

I should balance this out with other books, but I haven't read 'em yet. This book, however, was crucial for my own understanding — Scheuer actually takes bin Laden's words seriously, something I hadn't seen done before.

How should we understand the Black–White racial divide?

• Race Matters, by Cornel West AND
• Civil Rights: Rhetoric or Reality? by Thomas Sowell

(These authors couldn't disagree with one another more. Read them together!)

Should we hope, or despair?

• The Better Angels of Our Nature: Why Violence has Declined, by Steven Pinker*
• The Infinite Resource: The Power of Ideas on a Finite Planet, by Ramez Naam.*
• Radical Evolution: The Promise and Peril of Enhancing Our Minds, Our Bodies — and What It Means to Be Human, by Joel Garreau
• Nonzero: The Logic of Human Destiny, by Robert Wright.

THE WORLD NOW
Why are some people rich? Why are some people poor?

• Naked Economics: Undressing the Dismal Science, by Charles Wheelan.*
• Economix: How Our Economy Works (and Doesn't Work), in Words and Pictures, by Michael Goodwin.
• A Framework for Understanding Poverty: A Cognitive Approach, by Ruby K. Payne.

(Wheelan represents a center-Right perspective, and Goodwin a center-Left. Payne is very controversial, though I haven't yet found a substantive reply to her thesis — if anyone knows of one, please point me to it!)

Why are we suckers to advertisers?

• Spent: Sex, Evolution, and Consumer Behavior, by Geoffrey Miller.

What are we eating?

• Eating Animals, by Jonathan Safran Foer.
• In Defense of Food: An Eater's Manifesto, by Michael Pollan.

Why don't buildings fit people's needs?

• A Pattern Language: Towns, Buildings, Construction, by Christopher Alexander et al.

THE HUMAN MIND
Why are humans so weird?

• How the Mind Works, by Steven Pinker
• Kluge: The Haphazard Evolution of the Human Mind, by Gary Marcus.
• The Social Animal: The Hidden Sources of Love, Character, and Achievement, by David Brooks.*

Why is it so danged hard to be happy?

• The Happiness Hypothesis: Finding Modern Truth in Ancient Wisdom, by Jonathan Haidt.*
• The Depths: The Evolutionary Origins of the Depression Epidemic, by Jonathan Rottenberg.

(Haidt's work here is my favorite book — deserving of multiple re-readings!)

Why do people do horrible things?

• Evil: Inside Human Violence and Cruelty, by Roy Baumeister.*
• Confessions of a Sociopath: A Life Spent Hiding in Plain Sight, by M.E. Thomas.

(Baumeister's understanding of human cruelty is deeply challenging, and has been life-changing for me.)

How are some people so danged talented?

• The Talent Code: Greatness Isn't Born. It's Grown. Here's How., by Daniel Coyle.

(I have most of my students read chapter 4 of this book: "The Three Rules of Deep Practice." I've read a lot of books on expertise studies, and none distill the findings as well as well as this chapter.)

Why do rational people disagree with one another, violently?

• The Righteous Mind: Why Good People Are Divided by Politics and Religion, by Jonathan Haidt.
• Political Ideologies and the Democratic Ideal, by Terence Ball and Richard Dagger and/or Ideals and Ideologies: A Reader, edited by the same.
• The Blank Slate: The Modern Denial of Human Nature, by Steven Pinker.*
• God is Not One: The Eight Religions that Run the World, by Stephen Prothero.
• The Universe Next Door: A Basic Worldview Catalog, by James W. Sire.*

(The topics here differ: some are about religion, some about politics, some philosophy, and some all three! Sire's work is my second-favorite book, though I sharply disagree with its thesis. Pinker's book is the one I wish all undergraduates would read.)

Why does American education struggle to not suck?

• Getting It Wrong from the Beginning: Our Progressivist Inheritance from Herbert Spencer, John Dewey, and Jean Piaget, by Kieran Egan.
• Tinkering toward Utopia: A Century of Public School Reform, by David Tyack and Larry Cuban.

(In my perspective, Egan is our most under-read educational thinker. His other books — which don't fit your question — are also golden.)


NATURAL SCIENCE
What's this whole universe-thing, swirling around us?

• The Canon: A Whirligig Tour of the Beautiful Basics of Science, by Natalie Angier.

What's this whole evolution thing? (Where do we come from? What are we? Where are we going?!)

• The Blind Watchmaker: Why the Evidence of Evolution Reveals a Universe without Design, by Richard Dawkins and/or
• Why Evolution is True, by Jerry A. Coyne.

Here are some of the books that have most shaped my understanding of the world:

• Chimpanzee Politics: Power and Sex among Apes - I used to think that we were all rational beings, and that people generally did things for good reasons. (I know. I was young.) This book helped me see how the primate dominance dynamic is part of our genetic heritage, and a major way we operate in the world. It goes well with the following book:
• Impro: Improvisation and the Theatre - This book is nominally about theatrical performance and creating realistic scenes. But its section on status transactions is a clear, well-analyzed explanation of how the primate dominance dynamic plays out in moment-to-moment interactions between people.
• Vehicles: Experiments in Synthetic Psychology - Imagine a tiny robot, a free-running vehicle. By observing its behavior, what can we imply about it? And what do its simple mechanisms and our reactions to them tell us about ourselves?
• Zen Flesh Zen Bones: A Collection of Zen and Pre-Zen Writings - This has helped me recognize and accept the extent to which my mental models are just models, that the world will never be completely in my grasp. And that's fine.
• Consilience: The Unity of Knowledge - Legendary scientist E. O. Wilson looks at the relationship between the different spheres of human knowledge.
• The Selfish Gene - A fascinating take on evolution and how to interpret it. And as a bonus chapter, he coins the modern term "meme". In 1976!
• Good Natured: The Origins of Right and Wrong in Humans and Other Animals - As an atheist, my morality was never dependent on religion, but it wasn't until this book that I really understood the roots of human morality.
• Demonic Males: Apes and the Origins of Human Violence - It's popular in some circles to think of violence as an aberration, that if we all were started out right, we wouldn't have violent urges. This book helped me see that violence is part of my nature, and that I'll always have to be careful of that.