Here is a pretty easy but classic riddle.
What does man love more than life?
Fear More than Death or Mortal Strife?
What do the poor have,
The Rich Require,
and the contented desire?
What does the miser spend,
The Spendthrift save,
and what all men take to their graves?
That is the problem with a lot of the cooler older riddles, everyone has heard them.
I am thinking for this topic to just open up the last 3 chapters of the 3rd Dark Tower book and just start posting the riddles they use against Blaine.