This is a 4 DVD set that covers Machiavelli, his times, and his works. I have now watched it twice. Bill Cook does a spectacular job on this. It is currently on sale for $70 and worth every penny.
http://www.teach12.com/ttcx/coursedesclong2.aspx?cid=4311 Machiavelli is much more than "The Prince" Indeed, he would regard that as one of his more minor works. The theme Machiavelli wants to pound into people's heads is that you study history and find out what worked and why it worked. Just because it worked then, does not guarantee it will work now. But if you have a catalog of who, what, when, where, why, and what happened, you are much more prepared for the future.