2010.01.06
Many of these books were written before 2000... this is just a subjective list based on me first encountering them at some point over the last decade. But I'd heartily recommend any of them to nearly anyone.
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Zen and the Art of Motorcycle Maintenance, Robert Pirsig. The way this book tries to reconcile the Engineer's View (detailed, analytic) and the Romantic View (general, emotional) and come up with a sense of Quality that is really the heart of Daoism is astounding. It's also a nice and very human and readable story.
Consciousness Explained, Daniel Dennett. This book I cited again and again. It's a tough read, but I'm still amazed at the solid Western, academic structure it uses to get around to an idea that's fundamentally Buddhist; that there's not as much of a "there there" when it comes to consciousness as we think. (Jeff Hawkins' On Intelligence is similarly thought provoking, and it's idea that the core idea of the mind is "predict and test" is actually more relevant to AI than this, but hey, I can only put ten books on this list... while I'm cheating like this I'd point out that The Mind's I remains the best easy introduction to this kind of thinking.)
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The Great Gatsby, F. Scott Fitzgerald. I admit that in high school I ducked reading this book and Cliff Noted my way through it. I came back to it, thanks in part to reading about Charles Schulz' love of it. Now I'm convinced that it might not make sense until you've had a big unrequited love.
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The Mezzanine, Nicholson Baker. One of my favorite books of the previous decade was Tom Robbins' Still Life with Woodpecker, which taught me to stop disrespecting objects just because they're inanimate. This book combines some of that feeling with the thoughtful analysis of Donald Norman's The Design of Everyday Things, and maybe just a hint of "Rainman". Famously it takes place entirely during one man's journey across a mezzanine and up an escalator, but mostly in flashback over the few days prior.
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Things My Girlfriend and I Have Argued About, Mil Millington. In some ways not quite as pointed as the website that started it all, this is still one of the funniest books I've ever read. Admittedly men seem to dig this book more than women (even though some of the joy is the male unreliable narrator) and it is that "comedy of embarrassment" that some people don't dig.
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Feet of Clay, Terry Pratchett. This book is a stand-in for all the Pratchett I discovered and devoured over this decade. In many ways Pratchett is a more thoughtful and emotionally in-tune Douglas Adams. And I think this book is one of the best of the "City Watch" novels; the scene of Vimes defending the Golem was heroism at its most beautiful.
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How Can I Get Through to You?, Terrence Real. Recommended by the couples therapist Mo and I went to after the die had already been cast. What I most took away from it is the pattern that happens over and over, where a woman is unhappy with the growth of a relationship but doesn't want to nag, so doesn't say much, and the man is blissfully unaware and satiated, and the woman's discontent build and builds until it explodes, leaving the man stunned and bewildered.
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The Dharma Bums, Jack Kerouac. I guess a small theme on this list is Westerners discovering some of the ideas of the spirituality of the East; and this book has that in spades. It introduced me to the concept that "Comparisons are Odious" - a thought that sounds profoundly unsustainable until you think about it, and realize that it does represent a positive thought, and points to a different way of being in the world.
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Jar of Fools, Jason Lutes. I read a lot of Graphic Novels this past decade, and this is quite likely the finest; a very human and warm story, written with a compassionate eye and illustrated with a nicely restrained and clean, formal style.
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A Deepness in the Sky, Vernor Vinge. The lone sci-fi book to make the list...
I actually prefer the same series'
A Fire Upon the Deep and how it stretched my mind about possible idea for alien consciousness, but I guess I read that last decade.
(Similarly Permutation City is a decent story that plays with the "what ifs" of putting consciousnesses into VR worlds, but I guess I read it farther back than I thought.)
someone should do Video Game Hero: you pretend to play games with no real skill in using a rubbish plastic joystick and set to cheesy music