Tag Archives: gamble

Wealthy Man Riddle

Main Piece:

Informant: There was a very wealthy businessman and a woman on a flight who was sitting right next to each other. And the woman was just trying to get some sleep on her flight. But the wealthy businessman was like bored out of his mind so he decided to give the woman a trick. He said, “I’ll ask you a question and if you don’t know it, you pay me $5. Then you ask me a question and if I don’t know it, I pay you $500.” The woman was like “ok, fine.”

So the guy asked the woman, he asked her a riddle and she had no idea was it was, so she went ahead and gave him $5. Then the woman asked the man, “What goes up a hill with 4 legs, but comes down with two?” The man spent a really long time thinking about it. He called his friends, he looked it up, but he couldn’t find the answer anywhere. And then he finally asked her what was the answer. And she hands him back his $5. Because, she didn’t know the answer either.

Interviewer: Wait, what?


The informant is a twelve-year-old Native American girl from the Choctaw, Blackfoot, and Lakota Nations. She was born and raised in Tennessee and frequently travels out west to visit family and friends. She is in sixth grade.


During the Covid-19 Pandemic I flew back home to Tennessee to stay with my family. The informant is my younger sister. I asked her is she knew any jokes or riddles.


Proverbs, riddles, and.charms are three of the shorter forms of folklore. They are not necessarily confined to oral expression, having appeared in written literature for ages. The purpose of the riddle is usually to deceive its listener regarding its meaning. A descriptions is given where the answer must be deciphered. Many times riddles are used as a contest of wits. Regarding this particular riddle . . . story? The rich man was bored and used his money for entertainment. I honestly really don’t know what to say. It was kind of funny. (also, between us, could it be a murderer who went to bury a dead body . . .? Hopefully something much more pleasant).