Douglas Hofstadter's Godel, Escher, Bach: An Eternal Golden Braid. This book further explains the limitations of our thought processes, this time from a mathematical perspective. While it is at bottom a book about cognition, there is much more to it. It's a fun romp that ties together art, music, genetics and mathematics through a series of amusing dialogues.
Stephen Hawking's A Brief History of Time. In addition to his genius in thinking about the universe, Hawking's genius is also in making the confusing, counterintuitive concepts of 20th century physics accessible to non-scientists. Short and relatively easy to read, this book lays out the essentials of modern scientific thought.
John Perry's Dialogue on Personal Identity and Immortality. You will literally not know who you are after reading this very short, highly readable book. It will leave you floundering.
Stephen Pinker's The Blank Slate. Although I disagree with the majority of what Pinker says, I find this book very thought-provoking and important. While it is lengthy, there is an interesting thought on very nearly every page. I read all of the other books on this list by the age of 25. This is the only book that had changed my thinking in any major way since that time.
Robert Shea and Robert Anton Wilson's Illuminatus! trilogy. For sheer, mind-blowing fun, you can't beat this. Yes, it's long. Yes, it's dated. But it surely will show you just how much you don't know, and do so in a most entertaining manner.
Jesus of Nazareth's Sermon on the Mount (Matthew 5-7). Certainly I don't agree with everything Jesus says here, and it's quite a difficult set of rules to live by. Yet, it's definitely been a strong influence on me. Although these few pages supposedly form the basis of most western moral thought, relatively few ostensible Christians pay any attention whatsoever to what it actually says. I suggest reading it for yourself and giving it some critical thought.
Anthony Burgess' A Clockwork Orange. Although brief, this is a very difficult book to read, both in terms of the writing itself and the concepts conveyed. Stanley Kubrick's excellent film version is perhaps even harder to watch. This deeply disturbing story about crime prevention cuts right to the heart of our humanity. Kate Millett's Sexual Politics. While most classic feminist tomes are angry or poorly written in some other way, this book is sassy, witty and fun. It sets out the feminist basics through critiques of literary works, and includes a section on homophobia as well. It is somewhat scholarly and academic and not as readable as other books I have presented here.
Tom Robbins' Skinny Legs and All. Robbins has written many great works about how to be human. I absolutely loved this tale of Solomon's Temple, modern Arab-Israeli relations, and anthropomorphic underwear, with great life lessons in the interludes.
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