In the comments at Brian Weatherson's blog, I ventured the view that David Hume might be the greatest philosopher ever, and met with some opposition. I'll move my discussion here since it's not really topical over there. Just want to go through some of Hume's greatest hits:
The reduction of causation to constant conjunction is, for all its problems, probably the classic reductive move in the history of metaphysics. The epistemic considerations motivating it don't look so hot now that Logical Positivism's over, but they were influential for a long time (and I still find them pretty powerful). There's the antirealism about moral properties and the projectivist explanation that underlies it, which still inspires people like Simon Blackburn today. There's the attack on rationalist theories of motivation -- it's no accident that the field of practical rationality is divided between 'rationalists' and 'Humeans.' Hume's comments about the move from 'is' to 'ought' is the earliest clear statement of the naturalistic fallacy that I know of.
I mean, there's plenty of options for "greatest philosopher ever." I can see how you go with Kant if you like elaborate systems that save lots of our intuitions, or Aristotle if you're into the ancients and like logic, or Plato if you're into the ancients and don't like logic, or Kripke if you're an antirealist about the past and don't believe that the history of philosophy exists. But if you like reductive approaches and ontological simplicity, it's hard to beat Hume.
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