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I wish I had enough time and intelligence to study this stuff so that I can argue about it with someone. This shit is so cool, it’s basically how everything “modern” started. What great arguments can come out of discussing these few guys alone.
It's really fascinating. You have everything from the pseudo-totalitarian system of Plato to some Stoics who were outright anarchists to the 'Constitutional' ideas of Aristotle. What I don't know about classical philosophy could (and does) fill libraries, but I always love learning bits and pieces about it!
I highly recommend the podcast "Philosophize This!" It's by a philosopher who breaks down the core ideas of just about every significant philosopher in the western canon (and many non-western ones)
It's closer to maybe a lecture or an audiobook than just a casual conversation style podcast but it's really well done and very digestible, every episode is like 20-30 minutes. I have a lot more understanding of an overview of western philosophy because of it.
Go ahead and pick and choose a couple of philosophers you're interested them for a lot of the bigger ones he splits them into multiple parts focused on the different big ideas each philosopher brought to the table.