@DoctorTYVM
I did this last month with an idiot shiftless Hieracosphinx reluctantly guarding a treasure, and just had him ask the dumbest possible riddles in the most pompous and self-satisfied tone:
“Why did the chicken cross the road?” To get to the other side.
“Which came first, the chicken or the egg?” The egg. But he will argue.
“What is the difference between a duck?” One of its legs are both the same.
“What's got two wings and is going to eat you?” Point at the sky behind him and shout “That thing?!”
DM help: riddles in the dark
I’m working on a campaign that has the player meet a creature pretending to be a sphynx and ask riddles of the players....