The first time I read the chapter called "Riddles in the Dark" in The Hobbit as a young boy, I was captivated by the strangeness of Gollum’s character and the suspense of not knowing how Bilbo would fare in the riddle contest. If he won, Gollum promised to show Bilbo out of the mountains. If he lost, Gollum would eat him for dinner.

What really caught my attention was the moment immediately following Bilbo’s victory. He stumps Gollum (by accident) with the question, “What have I got in my pocket?” But Bilbo doesn’t trust Gollum to hold up his end of the bargain, despite the fact that “the riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it.”

At that moment, I can remember a couple questions coming to mind: First, how sacred was this “sacred” riddle-game? Second, how old, exactly, is “immense antiquity”?

I have since learned that there is a millennium’s worth of history behind the origins of riddles and riddle-games. One only has to think of the Egyptian Sphinx who sat outside the gates of Thebes asking this famous riddle of travelers who passed by:

“What creature has one voice, but has four feet in the morning, two feet in the afternoon, and three feet at night?”

The stakes for the traveler who encountered the Sphinx were just as high as they were for Bilbo. If a person answered the Sphinx’s riddle incorrectly, he would be eaten instantly. The Sphinx rarely went hungry. In his Theban plays, the Greek playwright Sophocles (497/496 BC) tells the story of the Sphinx’s eventual defeat. The ancient king Oedipus encountered the Sphinx and discerned the answer: “Man—who crawls on all fours as a baby, then walks on two feet as an adult, and then uses a walking stick in old age.” Having answered the riddle correctly, the Sphinx dies by throwing herself off a cliff.

In English, the word “riddle” is inherited from Germanic languages. The Old English word is rǽdels which had a wide range of meanings. Depending on the context, translators can translate the word as counsel, debate, interpretation, conjecture, imagination, dark saying, and—of course—riddle. The word is also specifically connected with ræd, another Old English word that meant wisdom or prudence. 

Rǽdels and ræd also happen to be the words from which we get our modern word “Read.” Riddles were used prominently in medieval classrooms as a method of teaching students how to read—which, by definition, entailed the acquisition of wisdom by means of interpretation. A student learns to read the “signs” of the letters on the page, and then how to properly interpret those signs in light of reality and human experience. 

Riddles were an ideal pedagogical method for two reasons. First, they afford multiple interpretations. It can be difficult to pin down a single right answer because they rely on the paradoxical connotations and observations associated with a single object. In his Enigmata, for example, Aldhelm describes the paradoxical qualities of a cauldron:

As pounded gaping metal – wide, gross, round –
I hang untouched by boundless sky or ground.
Glowing in flames and fevering with bubbles,
I thus confront two fronts with different troubles
As I survive both being scorched and drowned. (Riddle 49)

The cauldron is truly enigmatic in its composition: it is both “pounded gaping metal” and “round;” it is suspended between “sky” and “ground;” and it fights two battles against the heat of the fire and the potential drowning by water. The compounding paradoxes have the effect of helping the reader see the world anew—i.e., in its complexity and minute details. In the medieval classroom, students confronted these riddles on a daily basis not only to teach them how to read written letters, but to see the world more clearly.

Unfortunately, most of the surviving riddles from the medieval period don’t come with an answer key. Given their affinity for paradox, riddles often allow for multiple right answers. For example, here’s a section from riddle 47 in the Anglo-Saxon Exeter Book:
 

Bound in place, deaf and dumb,
Making a meal of gifts that come
From a man’s hand, she swallows daily
Sustaining treasures dearer than gold,
Brought by a servant, a dark thane,
Sought by kings, queens, princes—
For benefit and pleasure. What race
Of shapers makes such treasure for the dark,
Dumb lady to swallow is beyond my measure.

Given the lack of an answer key or evidence of how medieval schoolmen interpreted the riddle (not to mention the sheer number of paradoxes), the answer to this particular riddle is uncertain. Some scholars have speculated a laundry list of possibilities: oven, bookcase, mill, falcon-cage, and pen and ink. 

Instead of being a flaw, the possibility of multiple interpretations afforded by a riddle can be construed as a virtue. There may be a range of correct answers, but there is a far wider range of wrong answers which can only be determined by close attention to the details included in any given riddle. This exercise in reading elicits a kind of interpretive elasticity on the part of the reader which requires the mind to exercise its powers of observation, imagination, and logic to create a set of reasonable answers.

The habits of interpretation cultivated by the study of riddles highlights their second purpose in the medieval schoolroom. They were a training ground for learning how to interpret the scriptures. Most students received a formal education in the early middle ages because they were set on a path toward a priestly or monastic vocation where they were required to read, copy, gloss, or deliver sermons on religious texts. If a student could learn to interpret a riddle, then they could reasonably be expected to be a careful reader of Holy Scripture.

We might be tempted to think that comparing the scriptures to riddles is like comparing apples to oranges. A medieval schoolman, however, would counter that both the interpretation of riddles and the interpretation of the scriptures draw on the same human faculties of observation and understanding. There is some evidence in the riddles themselves of this comparison.

In riddle 40 of the Exeter Book, the speaker describes God as someone who speaks in riddles. Here, the speaker is “Creation,” and he says of himself:

I bind all turnings under heaven’s roof,
Guide and sustain as God first wrought,
Hold shape and form, rule thick and thin. 
I am higher than heaven—at the point-king’s command,
I watch and wield his world-treasure,
The great shaper’s riddle.

The translator of this particular passage has taken some liberties—instead of “riddle” the word should be “secret” or “dark”—but it remains true to the sense of the line. The mystery of creation has been set before us as a kind of riddle by God. One can almost hear King Solomon in Proverbs recalling that “It is the glory of God to conceal things, but the glory of kings is to search things out” (Proverbs 25:2).

Insofar as riddles are an imitation of God and His creation, the stakes are high. For medieval writers, riddles are as ancient and as sacred as creation itself. Riddles draw our eye and our attention to the mystery of the world we inhabit by defamiliarizing objects that we would otherwise take for granted. They initiate us into reality itself. Yet, such an exercise in reading, although it is imbued with cosmological significance, is also playful. A person, Geoffrey Chaucer writes in his Canterbury Tales, can say “full soothe in game and play.” The desire to understand the deep mysteries of our relationship with God and the world undergird our most ancient and sacred games. The riddle-game, when played well, may not only save us from the jaws of creatures like the Sphinx and Gollum, but may also usher us further into the wisdom, beauty, and joy of God’s creation.