The Prince
The greatness of the book is because the author destroyed a 2000 year old paradigm of thinking about how politics should work and introduced reality in to our way of seeing the world. There is an interesting meta-meta-history regarding this book. He's writing about using history before 1513, mostly Roman, and often relying on Plutarch, and applying it to his time period. From our modern perspective, it gives us the about-about-history (the meta-meta). The real lesson in the book is understand your history and know its context. The current time (be it 1513) or today are different from the past but lessons can be learned with caution. Overall, nobody should follow most of the precepts within that book because disaster will follow and the Mayberry Machiavellis of the Bush administration showed how history should only be your guide never you road map.
The author is quite quotable because he writes so plainly and relates ancient history to his modern times. "There are three kinds of intellect, the one who learns from himself, the one who learns from others, or the one who is incapable of learning". Or my favorite because of its complete inanity "fortune is like a woman, to master it you must first beat her, and mistreat her to make her your own". (sounds a lot like Nietzsche in his "Thus Spake Zarathustra"
