Man is the only animal that laughs and the only animal that riddles. In the joke and the riddle we take pleasure in looking at something one way and then having a revelation, which means we can never look at it the first way again. For example “Thirty white horses on a red hill, now they are champing, now they are stamping, now they are still– what are they?” Answer: teeth. When we hear the answer “teeth” for the first time we can never see those white horses as anything else, ever again.
Oedipus began his adventure solving a riddle. A fabulous monster — part woman part eagle part beast – asked him “What is it that walks on four legs in the morning, two in the day, and three at night.” Oedipus answered “Man” and the monster killed itself. Oedipus was confronted with a riddle to which the answer was himself at the beginning of his adventure. In the height of his adventure it happened again. He was confronted with a riddle in action — we call this a mystery — that went “Who did the horrible thing that caused a plague?” The answer to the riddle was the same. “I did.”
In both the riddle of the sphinx and the riddle of the plague the riddle answerer learned that the answer to the riddle was himself. So by answering the riddle he learned to understand himself differently. He changed himself.
Bilbo Baggins asked a riddle to Gollum who was originally Smeagol, a creature much like Bilbo himself, but who became corrupted. Bilbo’s riddle (after he had run through the horses/teeth one) was “What have I got in my pocket?”
Not a fair riddle! Gollum said.
Bilbo’s riddle was unfair because Gollum had no way of guessing it. And yet it was a cousin of Oedipus’s riddle. What Bilbo had in his pocket was the One Ring, which corrupted Smeagol into Gollum. It was a technology of self-transformation.
Oedipus was asked a riddle to whom the answer was himself. Gollum was asked a riddle and the answer was “the thing that gave you power and changed you into something very different.” Changed who into something different? Smeagol? Or Gollum?
That’s why it was a good riddle!
Tolkien’s story was about being perched on the knife’s edge between the world of paganism — what he called magic — and the world of disenchantment. You could say that Christianity for him was something like being perched on that knife’s edge.
Oedipus’s quest was to find out who had caused the plague. Bilbo’s quest was to find out what to do about the ring. The answer to Bilbo’s quest was to give it up, first giving it up to Frodo, and then ultimately having it destroyed in Mt. Doom — destroyed as if it never were. At the moment the ring was destroyed in Mt. Doom, Gollum died, and along with him the whole world of Faerie — ents, and elves, dwarves and hobbits. They went to the Gray Havens.
Two strange riddles, Oedipus’s and Bilbo’s, two strange quests. One riddle (Oedipus) had a simple answer — you. You’re the answer. The other, Bilbo’s, had a different answer — the thing that makes you no longer you. The riddle of Oedipus spurred a quest that led to self-blinding on Oedipus’s part, the riddle of Bilbo spurred a quest that led to the transformation of his world into one devoid of mystery, and devoid of him.
The world’s tangle passes through us; the knot in our heart and the knot in the sky are the same.