On Plato's Dialogue, "Gorgias" (380 BCE or so).
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Why philosophize? Isn't it better to know how to persuade people in practical matters, like a successful lawyer or business leader? Plato (speaking as usual through Socrates) thinks that the "art" of rhetoric (persuasive speeches) isn't an art at all, in the sense of something that requires an understanding of one's subject matter, but merely a talent for saying what people want to hear. Gorgias (and Socrates's other interlocutors) think that being able to persuade gives you power, so it's awesome, but Plato thinks that unless what you say is likely to improve your audience, then it's worthless. The argument is generalizable to all artistic endeavor: Do the arts aim to just give pleasure, and even if they do, is that bad?
Mark, Seth, Wes, and Dylan kick this one off with some discussion of how we pick topics, and then stroll through the this very entertaining dialogue, which you can also hear us read in "Not Episode 69." We consider Plato's doctrine that knowledge inevitably leads to virtue and his insistence that goods can't contravene each other, so that pleasure over an injustice can't be good just because it's pleasurable, and acting justly must always be in our long-term interest, by definition. We wrap up by joining Socrates in dissing those that would dismiss philosophy as a waste of time. Get the book and read more about the topic.
End song: "Fallen Sun" by New People, from the new album Might Get It Right (written/sung by Matt Ackerman).