Snaz, from Ultima VII
Snaz is a beggar living on the streets of Britain. Despite his poverty and misfortune, he tries to take it with humor and make money by telling jokes, instead of begging.
Snaz didn't talk much about his past when found on the streets in Ultima VII, only cryptically hinting that life had been unfair, leaving him a poor orphan in his childhood. He offered to tell the Avatar jokes for one gold piece each. His jokes were quite varied and involved: the Fellowship, Lord British, Weston, Mages, Sullivan and Gold Coins.
Surprisingly, he gave the Avatar, after telling the joke, some rather interesting insights on each of these things, hinting that he was way smarter than he let on. For his final joke, Snaz merely took the Avatar's gold. He did so until the Avatar wouldn't pay any more, then claiming that the hero had won insight.