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1) So many to choose from, but--Adolf Hitler; after all, he is one of history's greatest villains. No doubt about it, he stands out from other tyrannical rulers. But this choice is two-fold: it is about the man himself (his life, his evolution) and it is the movement he led, and the consequences of it. I am a keen enthusiast on the World Wars but especially the Second. It is one of history's greatest dramas and this man was at the forefront of it; he led the world into the abyss and it took three major world powers to lead humanity out of it. Almost by himself, he built the impressive regime that was the Third Reich and equally by his own doing, he reduced it to ruins. I just don't see how any could NOT be fascinated by him. And it's not just the historical side of Hitler that is fascinating. The psychology behind Hitler is equally fascinating. Terribly evil as he was, one never grows tired reading about him or watching documentaries.
I know you asked for one but now I'd like to name a "good guy".
I love philosophy (it was my major in college) and I have always been enthralled by the Danish philosopher, Soren Kierkegaard, who is the father of existentialism. But it is not just the man's life works that are enthralling, but it was the figure himself as well. He was a key figure to bring philosophy back as a "way of living", like many of the ancient Greek philosophers from abstract theorizing that was philosophy throughout the Medieval and post-Medieval period up until his time. He was an enigma and he chose to endure individual anguish for what he believed in. A great fascinating aspect of his life was his authorship; he would write in pseudonyms mostly, not only to hide his identity, but for the sake of making various philosophical viewpoints befitting of each individual pseudonym. He was a man who wanted to heard but not to be seen and his entire life could have been a great movie; biographies written about him are often enthralling because of this aspect.
2) Depends on what we mean by judging. We can judge the past and its figures based on grounds of prudence. We often critique certain historical figures for what they had done, what they gained or lost from those actions, and then we implement an alternative that might've worked for them, or could've made it bad for them (if only the Titanic had more life boats; what if we had not dropped the bomb on Japan--what would a mainland invasion be like?).
Moral judgment is a different matter though and it is a concern that is most prevalent in our time, and the challenge is to be fair in this judgement without surrendering to a form of moral relativism. Many things that were considered normal at one point in history, such as slavery, has always been a great evil since it first started; however, it is wrong to apply the naive mode of thought known as "presentism", because we all want to think of ourselves as someone who can say "if it were me, I'd have done the right thing" but this is just nonsense. It is when we judge past figures exclusively by our own sense of morality that we sort of water down history by ignoring the reality of the times, and focusing on the present.
