I just finished rereading Machiavelli's The Prince. I last read it about 12 years ago. It made a real impression on me then, but I thought I have a slightly different take on the world now, and I had forgotten most of it. Wooton's introduction is pretty good.
This is the book that introduced the world, systematically, to power politics. There is much in the book to consider and take seriously, and no doubt millions of people over the past 500 years have. I think that it might be a good exercise to rewrite The Prince using modern examples. The examples are not really necessary for the book to make its point, but almost every chapter has some examples. They serve to make the book a more interesting read, and also to support the conclusions. It would be instructive to use examples from the last 50 years of history to see how applicable. I suspect that it would be informative to see that there are some places where he was wrong. It would also demonstrate the amazing relevance the book still does have, despite the radically different natures of governments, warfare and religion. Perhaps some enterprising history teacher might want to try this?