Ask a Long-Dead Philosopher
If you could ask a long-dead philosopher any one question, who would you you pick, and what would you ask? (For our purposes here, “long-dead” will mean “died 50 years or more ago.”) Post your question in the comments. Folks are welcome to try to answer, too, as they think the philosopher asked would do so.
On the assumption that the answer can be in essay form, and that the question can require the philosopher to do some extra reading, the funnest thing would be to expose geniuses to what others had done with their work.
You could ask Schopenhauer what he thought about Nietzsche (the torrent of abuse would be tremendously entertaining, if nothing else) or Carnap (of both Meaning and Necessity and Empiricism, Semantics, and Ontology) what he thought about Kripke (maybe Timothy Williamson built a time machine and did this).
It would be hard to do this with Kant because he really pushed up against the limits of encroaching senescence. At the very time you’d be asking him about what the German Idealists made of the first critique, he wouldn’t have much time for you because he had to finish the third one. This maybe happened to some extent with respect to Sholze, early Fichte, and Maimon.
I’d have Kant read Van Cleve, Allison, Guyer, Allais, and Langton and then ask him, “who was closest to faithfully representing what you meant about the noumena/phenomena distinction?”
To Plato: What do you really think?