The Bible.
Not for any religious reason, but because it underpins so much of Western art, culture, and literature. If you have not read it, you will miss out an awful lot.
1984.
Not necessarily because I believe it will happen (in that exact way), but more because it rings to attention many problems that are appearing/being revealed in modern society. Specifically, the many ills, laws and other regulations inserted by states in many parts of the Western world.
The Republic by Plato.
It lays down so many of the reasons we have now for why we do things. You just have to read it if you're in anyway interested in any sort of academic pursuit.
Zen and the Art of Motorcycle Maintenance.
Brilliant, unsettling and impossible to put down.
Slaughterhouse Five by Kurt Vonnegut and The Things They Carried by Tim O'Brien.
Both are war related (WWII and Vietnam, respectively) but they are so beautiful, deep, touching and really give a deeper look into war and it's effects on people, especially the soldiers fighting it.
The prose is enthralling, compelling and if you don't cry in at least one part of either book, or at least have it make you contemplate life and humanity, then I don't know what to tell you.
Siddhartha.
Each time I read it I learn something new or gain a new vantage point. I grew up catholic and before this book, I had NO exposure to the concept of no-self. I literally never had anyone in my life ever even hint about such a concept. Looking back on how much change has entered my life since then, I consider reading that book to be my "opening the wardrobe to Narnia" moment.
How to Win Friends and Influence People.
The reason why this different than your standard fare of self-help book and why it has withstood the test of time is that unlike other self help books, it isn't a simple "read this and it will change your life instantly."
Rather it is a book delineating a regimen for slow, incremental change that requires time to implement, and constant review (the author encourages constant re-reading of chapters.)
But once it is implemented, your life will change, and your social interactions and career will literally change, just not overnight.
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