Who has sympathy for the Devil?

A working class man finds himself seated across from the Devil. A charming, attractive man who asks him to simply have a conversation. Petrified at first, how could he say no? As the conversation progresses, he realizes he's enjoying the conversation and looks forward to the next time he can sit down for a chat. The conversation is an introduction to philosophy on a rather broad scale. It introduces, by way of conversation, the ideas expressed in the philosophy of Socrates, David Hume, Søren Kierkegaard, and Jean-Paul Sartre - all subtly expressed through the guise of understanding the perspective of a skeptic and contrarian. The ideas posited by these philosophers went against the grain of common ideology, therefore, who best to champion them than the original contrarian?