Ahhhh Steven, such rich questions.
First, allow me to address the subtext of your comments about the unique magic that riddles hold. You rightfully say, “It’s not like we have any experience with riddles in daily life.” I think this is EXACTLY why riddles delight us in such profound ways. The idea of a toll taker requiring us to solve a riddle in order to pass over a bridge would border on absurdity, taking us out of our common daily realm to somewhere else — or at least to a liminal space between reality and absurdity. Perhaps the map that riddles provide to this liminal space is what makes them kin to the family of myths, fairy tales, and folklore.
I think it’s also of interest that you said “riddles take me back.” I share that same experience. Not only am I taken back to a younger physical “self,” I am also taken back to a time when wordplay was important to me. I, too, loved books of riddles, as a child. Through the aging process, I have been drawn into other matters of concern, and often forget about the simple yet profound joys that clever words can bring. It’s not even a matter of simple enjoyment, there seems to be something deeply meaningful happening in my unconscious when I contend with a riddle. Perhaps it is working at a level I am not fully meant to provide articulation to. I often feel a sense of mystery under the surface of a riddle that feels connected to the mysteries I encounter in myth and fairy tales.
You ask about what riddles might have to do with the mythic imagination and I am thoroughly drawn into thinking about games, and their importance. Riddles could be considered a sort of game and psychologists are fairly unified in their opinion that games are important to our human development. I would be so bold as to suggest that the imaginal games we engage in as children are an expression of the mythic imagination. I would pretend to be Luke Skywalker when I was a young boy. I set out on adventures and battles with the dark side. I now look back and recognize that I was exploring the mythic in my imaginal games through the means most appropriate to my maturity at the time. (Full disclosure — you MIGHT sometimes still catch me dressed up in Star Wars attire at certain comic conventions.)
I’ve been thinking a great deal about game theory and re-reading Finite and Infinite Games by James P. Carse, which I consider a masterpiece, through a mythic lens. I wonder if anyone else might have thoughts about the intersection between riddles, games, and myth? I believe this intersection is a pathway into Campbell’s exploration of Finnegan’s Wake.