The word riddle was first recorded before 1000 AD in Middle English. Close to the Old English rede, meaning story. A puzzling question stated in such a way as to require a clever answer.
The oldest recorded riddle is actually a mathematical problem written in cuneiform from around 1650 BCE, called the Rhind Mathematical Papyrus.
There are seven houses;
In each house there are seven cats;
Each cat catches seven mice;
Each mouse would have eaten seven ears of corn;
If sown, each ear of corn would have produced seven hekat of grain.
How many things are mentioned altogether?
The usual answer: *** one (1) ***
Other answer(s) are a bit disappointing.
The most famous old (470 BCE) riddle is The Riddle of the Spinx from the myth of Oedipus.
The riddle: “What being has four legs, then two, and then three?”
The answer: *** “Man, who crawls on all fours as a baby, then walks on two legs, and finally needs a cane in old age.” ***
Check out the medieval riddles located HERE and HERE.
The ever-prolific Voltaire wrote this riddle:
"What, of all things in the world, is the longest and the shortest, the swiftest and the slowest, the most neglected and the most regretted, without which nothing can be done, which devours all that is little and ennobles all that is great?"
The answer: *** Time ***
My attempt at riddle writing:
Born earthbound and starving, I sleep in my shroud and hatch to soar less than a lunar cycle.
The answer: *** a butterfly ***