I'm personally a big fan of Camus and Nietzsche. "The Stranger" was a masterpiece, and Nietzsche's aphorisms are brilliant. I agree with both of them on a lot of topics, but even if I didn't agree with Nietzsche, just reading his work is worth it. It's very well written.
I am not very well read on philosophy as I tend to read lots of random articles and watch various documentaries but I find some of the philosophers from the Enlightenment era to be particularly interesting like Voltaire. Then you have Plato and the allegory of the cave which took me a while to understand but when I did it blew my mind!
While I agree that Nietzsche is interesting to read, I find that I need more modern philosophers in order to understand the background they come from. Nietzsche does on occasion jump to weird conclusions and justify it in what today are bad ways. I might have to go with Rawls at the moment.
Actually, I'll say C Wright Mills. He's pretty legendary... He's more a sociologist, but his stand on society often cam around to demonstrating a philosophy on society and the nature of information, awareness, and ethics within that society.
I think they are like pop culture artists. They are fantastic when they remain general, but the closer you get to the core, the weirder they're views become. I guess it's a lesson that you cannot iconolize just one mind (like a Jesus or Buddha) but must continuously apply principles to the present.
The cave is a really good analogy that persists... My teacher had said that each human being was his own cave. And human groups where varying degrees of social caves, and each cave was an echo chamber where ones own thoughts received validation from like minds. He made a really good case to show how American society was really a group of insular caves and technology only made this worse, not better, because the cave mentality is not a condition of force, per se, but of limited perspective and, because of that, limited choices and actions. We only act based on the information we receive, thus if we pay attention only to one perspective, our perception of the world and our ability to react, accurately, to it is severely impaired. Really good teacher. Teachers don't get half the credit they deserve...some of them.
Your teacher sounds like a wise person. To me the cave also represents boxed thinking. Sadly I think most that I know self centralize their experiences and then apply their experience to all humanity. To a degree it makes sense that as a human if I am effected by a thing, that you as a human should be effected in the same way as I. I thought that way for an embarrassingly long period of my life but in the end came to see the folly in such insular thinking. We are all trapped in the cave/box including myself... but as time goes on I fight to push back the walls and knock holes in the ceiling. Perspective is an amazing thing and I no longer want to be trapped by my own thus I am so thankful for the perspective I get on the forms from people like you and others.
Nietzsche, La Rochefoucauld, Marcus Aurelius, Machiavelli, Plato, Seneca, Confucious, Foucault, Hardt, Negri are some notable ones to me, and this doesn't count the anonymous or one off works of others.
Which reminded me of a song of my youth: [video=youtube;8tlDeVyeCOc]https://www.youtube.com/watch?v=8tlDeVyeCOc[/video]