Here are some books I recommend on a variety of subjects that interest me. (Thanks to Amazon for saving my complete order history since 1999.)

Philosophy of Mind

This is in the order that I would recommend reading them. (Indeed, it is the order I read them in, and it worked for me!)

• The Mystery of Consciousness, by John Searle. This being the first book I read on the subject, I don't actually recall what it was about, although what I remember is that I got a new perspective on questions of the nature of the mind, and the mind/body problem. Searle raises the notion of the "emergence" of the mind out of the brain, but as I recall he doesn't say what that really means (and in other works he takes a fairly peculiar (read: I think he's wrong) view that consciousness cannot be replicated on a machine, so I wouldn't take Searle too far these days).
• Views into the Chinese Room: New Essays on Searle and Artificial Intelligence, by John Preston. I read this long ago and my memory of it is dim, but I recall it as raising a number of interesting questions about the nature of consciousness, though perhaps not addressing them satisfactorily.
• Supervenience and Mind : Selected Philosophical Essays, by Jaegwon Kim. A long book on the notion of supervenience, as a type of physicalism that leaves something interesting to explain about consciousness and the mind. While supervenience is undoubtedly true in some form, the book didn't actually address those interesting things that need to be explained.
• Physicalism, or Something Near Enough, by Jaegwon Kim. Most recently cemented my view of the separation of qualia from other supposed properties of consciousness as special. Really good. Clear and short recap of issues of causality and physicalism.
• I Am A Strange Loop, by Douglas Hofstadter. It's no GEB (see below), but nevertheless an entertaining and thought-provoking ride through the comparison of the "inner light" in self-aware beings and the Gödel's "strange loop" of twisting a proof system inside itself. The main point: "I" is an illusion, a result of the mere way that our brains organize the universe, and nothing other than a pattern of computation distributed throughout the universe.

Logic, History of Science, Etc.

• Soul Made Flesh: The Discovery of the Brain--and How it Changed the World, by Carl Zimmer. A brief history of the discovery in the western world of the functions of the heart and brain. Well written, easy read.
• Gödel, Escher, Bach, by Douglas Hofstadter. Formal logic (Gödel's incompleteness), formal language theory (Turing and Church), some 1970s artificial intelligence (SHRDLU) and programming, mixed with commentary on Bach's music, M.C. Escher's art, and humorous stories involving the fictional characters Achilles and Tortoise. Good though it might be for learning about any of these things, it might be better already knowing (some of) them to appreciate the humor and elegance of the book. A very long read, but worth it.
• Looking Backward, by Edward Bellamy. I read this utopian dream in High School, for class, and, well, I liked it a lot then, so I might as well list it now.

The Media, Copyright

• The Creation of the Media, by Paul Starr. Excellent history of the development of the press from the first newspapers in the 17th century through to the creation of the broadcast TV networks in the mid 20th century. Makes good points about how regulation of an industry can be bad for consumers in the end.
• Anything by Lawrence Lessig... such as Free Culture. Why copyright law should be different from property law, among other things.

Linguistics

• Skeptical Linguistic Essays, by Paul Postal. A critical look at various topics in linguistics. Good sections on "junk linguistics." Amusing, in the sense of "this is the field I'm in?".
• Formal Semantics: The Essential Readings. Good collection of some of the classic papers in linguistic semantics. Many are quite dense, but that's why they're classics, I guess.