This conversation has made me want to read Hume, thus – on that note, is there anything in particular you think I should pay attention to?
I think Alejandro1 gave a good answer as well, but my answer will be slightly different.
I'd suggest starting with An Enquiry Concerning Human Understanding if you're more interested in epistemology, or otherwise An Enquiry Concerning the Principles of Morals if you have greater interest in the foundation of morality, ethics, justice, etc.
As the familiar story goes, Hume wrote A Treatise of Human Nature, and then found the reception for this work to be extremely unsatisfactory (everyone seemed to misunderstand it, and many just ignored it). He decided that...
Since LessWrong is a major congregation point for certain philosophical ideas, and because people here tend to be more objective (in the sense of not being self-deluded) than elsewhere, I thought I'd ask people's views.
To be clear, by "Greatest Philosopher" I am referring not to the most correct philosopher in human history but the one who deserves the most credit for advancing human philosophy towards being more true.
Off the top of my head I would say that a prime candidate would be Hume- amongst other things he rejected the idea of a soul, realised to a much greater extent than his predecessors the limits of human knowledge, and opposed the idea that reason is somehow an objective force that can make priorities independent of emotions.
Aristotle deserves considerable credit relative for his time but doesn't make the list because although it wasn't his fault his ideas were dogmatically accepted and held back both science and philosophy later on.
Your thoughts?