Plato's Republic

Any freedom loving person will hate this book if he reads it as a straightforward exposition of how to achieve the ideal state, because the ideal state Socrates describes in the book (the "Republic" of the title) is a terribly tyrannical place.  But it doesn't seem to me that Plato intended it to be read that way.  It is more like a thought exercise, where Socrates poses questions, and depending on the answers of the person he is speaking with, takes ideas further, step by step.  Some of his dialogue partners have real input; others seem more like yes-men--sometimes reluctant yes-men--and Socrates's exchanges with them read like cautionary tales showing the crazy places where lazy thinking or gullibility can take you.  And of course, nowhere is lazy thinking more dangerous than in politics, where a lot of harm can result.  There is a part where Socrates describes the three different kinds of acceptable government, the three evil kinds (which are the three acceptable ones taken to extremes), and the three different personalities that tend to be produced by each type of government, and also this is the book where Plato describes his famous "Cave" analogy.

All in all, a very rich book--one that deserves to be read multiple times, because you won't get everything it has to offer in one reading.  It's definitely a book that is best read at leisure, because there are a lot times when you will have to stop and think about whether you agree with what you just read or how you would have answered Socrates differently from his dialogue partner.

Peter Kreeft did a great series of lectures that serve as an introduction to Plato and his work--very useful if you haven't read any Plato before.  I think I'd have gotten more out of this book if I'd heard the lectures before reading it.