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The Most Dangerous Game:
Capital Riddles in Western Culture


“Off with her head!” An original illustration for Lewis Carroll’s Alice in Wonderland (1864)

7,655 words

The Sphinx-riddle. Solve it, or be torn to bits, is the decree.

— D. H. Lawrence

A question, readers: what is the most profound of all human activities? With the previous sentence, I’ve already provided the answer, for it is the question itself — the thing that drives all exploration and philosophy. How can philosophy (or any knowledge) exist without first the riddle, the profound need for the answer? Such questions, straddling the line separating knowable and unknowable, “made poets out of priests and sacred philosophy out of profane recreation.” [1] [2] In the oldest civilizations, there may not have been much separation between play and prayer at all, for in those times and in those places, gods were tricksters. Olympians loved to sow discord among themselves and their mortals on earth, often with deadly repercussions. The Old Testament God gambled with the devil for the fate of mankind. “How does the wind not cease, nor the spirit rest? Why do the waters, desirous of truth, never at any time cease?” “Don’t you want to know what it feels like, what the fruit tastes like? Don’t you want to know?” hissed the serpent. Such queries explain why scientific scholars in the early modern period referred to themselves as “natural philosophers.” The scientific method, after all, begins with a question.

Yes, words are magical things that can both signify and hide their meaning, and it was the Greek philosopher Aristotle who invented the word “metaphor” (metapherein meaning “to transfer”) in his Poetics and Rhetoric (ca. 400 BC) to explain how language created “infinite meanings with a limited set of resources,” suggesting that metaphor and riddles are often one and the same. Read them for literal interpretation, and they will elude you; think beyond their prosaic definitions and remember that “words are magical things,” and the solution may strike like a bolt from the blue. They may too, have achieved their popularity because of the great store Classical societies placed in oral storytelling and learned debate; the Socratic method involved an often riddling question and answer session that would, ideally, lead to enlightenment — to the gold flash of truth in a silt pan. [2] [3]

Riddles are metaphors for existence and the double-faced nature of humans themselves, for they are often both playful and serious, warning and entertainment, “mystical and trivial,” sometimes a reverent prayer, a meditation on the nature of being and the universe — and sometimes they are a taunt. They emerged during the same time as the ancient myths and legends, for they were mini-mysteries, whose insights revealed the meaning of the world around us, and the most famous riddles asked questions of vast significance. Many believed that only special individuals with the gift of clairvoyance [4] could solve the revelation-conundrums spoken by the god-creators through their oracles (like most ancient religions, anointed priests and priestesses acted as intercessors between the divine and earthly realms). [3] [5]

White people have been especially gifted at problem-solving throughout their history, have always been hungry for answers, have been driven to know everything. The day we stop asking questions is the day we stop being European men and women, for its process is the indispensable friend of the truth. Sooner or later, questions and riddles almost always dredge it up from even the murkiest of waters. And for these truths, these precious pearls of wisdom, we have been willing to risk all. It is this marriage of danger and knowledge, question and answer, risk and reward that defines the riddle, for it is a gambling game. Questions themselves have peril attached to them, for you may not like their answers. Sticks and stones, readers, but riddles carry the real threat of violence. Behind their whimsy lie death and entrapment; a cerebral-mind game that might nevertheless become savage. “Riddle-contests” in archaic societies were duels with deadly consequences, thereby making the riddle a kind of ceremonial sacrifice. Solve the mystery, provide a pleasing answer — or forfeit your head. Indeed, riddles with their usual poetic rhythms bore more than a little resemblance to the sacred danses macabre discussed in a previous essay [6]. This article will explore the “Capital Riddle” and its four paradigms (some riddles discussed I could place in more than one category) in Western culture: weak against powerful; like battling like; trickster taunting authority; and chaos threatening order. For the riddle is all of these and more.

Outwitting Monsters: The Trial 

Indo-European traditions glorified the brawny warrior and the wise man, both — but the wise warrior was especially revered (hence the undying appeal of Athena and her favorite hero Odysseus). Our oldest recorded riddles and enigmas often pitted the comparatively weak against the comparatively powerful: mortal vs. god, monarch vs. peasant, man vs. monster, and they were always games with the highest of stakes on the line. The heroes in these tales solved the paradoxes put to them with the aid of intelligence and verbal ingenuity, and so fulfilled the human desire to do the impossible: cheat death and damn the consequences. These powerful threats tested heroes on their journeys toward home, adulthood, the long quest, or the greater lesson — a way to both entertain and enlighten listeners in those early oral traditions most famously represented by the Greek poet Homer and his dramatic descendants.


Gustave Moreau, Oedipus and the Sphinx, 1864; barely inside the frame, the limbs of the Sphinx’s dead victims clutch rigidly to the red rocks below, just as the Sphinx herself clutches, almost seductively, at Oedipus’ dominant frame.

Said to guard the way to the city of Thebes (an ancient Greek settlement in Egypt), the Sphinx with the head of a woman, the wings of a falcon, and the body of a lion/leopard, tore the flesh from those travelers who could not answer her riddles. The best-known story of the Riddle of the Sphinx is from Sophocles’ Oedipus the King, a drama in which Oedipus reminded his subjects how he had rid them of the monster who’d long haunted their roads with death and dismemberment. Oedipus, having been exiled at birth from his father’s court because of an ugly prophecy, had grown into a young man, hungry for glory. He thus began his journey from Corinth toward Thebes and his inheritance. He had several adventures along the way — a physical battle with an older man that ended in the “stranger’s” death, and a mental battle with the notorious Sphinx. The beast barred his way and demanded the youth answer its question, or die: “What walks on four feet in the morning, two in the afternoon and three at night?” Oedipus then gave the solution to the metaphorical riddle: “Man,” for he crawls on four limbs as a babe, walks upright on two legs in his prime, and hobbles along with a walking stick during old age. [4] [8] Defeated at last, the Sphinx allowed Oedipus to pass unmolested into Thebes, where, for his great deed, Oedipus won the old king’s throne and married the widowed queen. All things considered, it might have been better had he provided the Sphinx with a bad answer. But there is no tragedy without some greatness along the way.

While on his own tortuous journey homeward bound, Odysseus too had to contend with demons disguised as beautiful women. The way from Calypso’s island took Odysseus and his crew near the Sirens, who “sensed at once a ship / was racing past and burst into their high, thrilling song,” which was also a riddle:

Come closer, famous Odysseus — Achaea’s pride and glory — moor your ship on our coast so you can hear our song! Never has any sailor passed our shores in his black craft until he has heard the honeyed voices pouring from our lips, and once he hears to his heart’s content sails on, a wiser man. We know all the pains that the Greeks and Trojans once endured on the spreading plain of Troy when the gods willed it so — all that comes to pass on the fertile earth, we know it all! [5] [9]

Though seeming to promise liberation from care and pleasure — wisdom, even — the Sirens were, of course, only promising a violent end, death being the answer to their riddling song of “sailors passing” and “ships mooring.” A literal man, drawn like a tired bird to the rumor of trees, might have accepted their offer, but Odysseus and his crew, forewarned, knew they spoke in metaphors, knew the kind of “rest” with which the Sirens tempted them, the tired sailors, was not one of short duration, but that which lasted for all eternity.

In an apocryphal story about Alexander the Great, which reversed the usual formula of questor and questioner, it was the traveling warrior himself who asked the riddles and lost the Capital Game. Angered that a conquered Indian city had dared resist his demands for surrender, Alexander summoned the ten wisest men from the defeated populace and charged them with answering his queries (“which is more — the Living or the Dead?”; “which is greater — the Land or the Sea?”). The young conqueror chose one among them to act as arbiter and to sit in judgment over his fellows’ replies; the man who guessed worst would be the first to die. But the appointed judge played a trick of his own, and when Alexander demanded that he decide who from among the group had given a bad solution, the sage answered, “each worse than the other!” thereby foiling the plot and saving all ten lives. [6] [10] Indeed, there was an honor code involved in each of these encounters. Should the guessers prove themselves mentally adept and provide a clever reply, the questioners had a duty to spare them; as in all contests of skill, rules had to be known and followed in riddling games, even by the most powerful of players. After all, the universe itself was governed by unalterable laws that no one, not even the gods, could break.

If anything, medieval people loved their riddles more than the ancients did, and Geoffrey Chaucer’s “Wife of Bath’s Tale” continued the traditional formula of flawed hero, quest, and conflict between the sexes. Chaucer’s narrator, the Wife of Bath, had run through five husbands and so esteemed herself “knowing” and wise in such matters. Her story began once upon a time in the golden days of King Arthur’s court, when goodness and justice reigned over weak and strong, noble knights and tillers of their fields, all Britons young and old, when “the elf queen with her jolly company danced often in many a green meadow.” [7] [11] And so when a wandering knight, “a lusty bachelor, who one day came riding from the river,” saw a maiden walking alone and “then, against her will, and by pure force, took her maidenhood,” there arose great outrage among the people. [8] [12] King Arthur, according to the laws of Camelot, condemned the man to death for his crime. But the queen begged him to spare the knight and give him up to a task she should choose for the doomed fellow. Because Arthur could scarcely deny Guinevere anything, he agreed and sent the man to prostrate himself before the queen and her ladies. Addressing him thus, she warned the knight, “You are still in such a position . . . that you have no guarantee of your life as yet. I will grant you life if you can tell me what thing it is that women most desire . . . And if you cannot tell me now, I will still give you leave to go a year and a day to seek and learn a sufficient answer in this matter.” [9] [13]

Needless to say, the bachelor was baffled and had no choice but to spend the next year questioning any woman he met on his quest for knowledge — the key that would unlock the mystery of the fair sex. And it was a mystery, for “he reached no land where he could find two people who were in agreement with each other on this” riddle. Some said “riches best; some said honor; some said amusement; some rich apparel; some said pleasure in bed, and often to be widowed and remarried; some said that [women’s] hearts are most soothed when [they] are flattered . . . he came near the truth there,” the Wife of Bath admitted. [10] [14] Still, the longed-for flash of insight eluded him. How could he himself know the riddle of the female sex when an entire kingdom of women could not tell him? In the end, of course, the bachelor-knight resolved the conundrum to the satisfaction of Queen Guinevere and saved his head from the block, but I’ll not spoil it; if readers wish to know the answer to this amusing story, I direct them to Chaucer’s Canterbury Tales.

Latter-day authors who have delved into myth, legend, or who have sought to create their own mythological worlds, have often used the Capital Riddle game as a plot device, mirroring older storytellers’ insistence on establishing the hero’s quest as one of trial by combat. J. R. R. Tolkien’s unlikely hero Bilbo Baggins was a hobbit who had once been happy to stay tucked away in his cozy house burrowed into the side of a hill, to eat his twelve meals per idle day, and never, he resolved, would he take any risks or adventures that would endanger his reputation as a hobbit of leisure. Fate had other ideas, and before long, Bilbo fell into the company of thirteen dwarves and a bumbling wizard, all of whom were on a quest to reclaim their treasure stolen by a malevolent dragon named Smaug, who guarded the enormous horde of gold and jewels from inside the Lonely Mountain. Poor Bilbo soon found himself at the mercy of any number of nasties: trolls, man-eating spiders, goblins, and perhaps the most disturbing creature of all — Gollum, an emaciated, semi-hobbit-like resident of the caves deep below the Misty Mountains.

Somehow, Bilbo lost the group while crawling his way through the tunnels that “seemed to have no end,” and he stumbled upon something that shone in the dank light of the water — a gold ring. [11] [15] Then, he encountered something more unpleasant — the ring’s owner, “old Gollum, a small, slimy creature . . . as dark as darkness, except for two big round pale eyes in his thin face.” Gollum lived off blind fish, “which he grabbed with his long fingers,” and goblin, too, “when he could get it . . . throttling them from behind, if they ever came down alone anywhere near the edge of the water while he was prowling about.” [12] [16] Now, with his large and liquid telescope-eyes, Gollum spied what promised to be an extra-tasty piece of meat. Bilbo hastily hid the ring in his pocket as Gollum paddled toward him. He then drew his elven sword, halting Gollum’s advance and making him, for the moment “quite polite,” at least “until [Gollum] found out more about the sword and the hobbit,” and whether Bilbo was alone as he seemed. So, the bizarre monster proposed a riddling game as a stalling tactic, for “asking them, and sometimes guessing them, had been the only game he had ever played with other funny creatures sitting in their holes in the long, long ago, before he lost all his friends and was driven away, alone, and crept down, down, into the dark under the mountains.” [13] [17] And to sweeten the pot, Gollum promised to show Bilbo the way out of the mines should the hobbit win their game. But if Bilbo failed to answer Gollum’s riddles, “we eats it, my preciouss!” Gollum hissed,

What has roots as nobody sees,
Is taller than trees
Up, up it goes,
And yet never grows?

An eye in a blue face
Saw an eye in a green face.
“That eye is like to this eye,”
Said the first eye,
“But in low place,
Not in high place.”

It cannot be seen, cannot be felt,
Cannot be heard, cannot be smelt.
It lies behind stars and under hills,
And empty holes it fills.
It comes first and follows after,
Ends life, kills laughter.


Alan Lee, “Riddles in the Dark,” a scene from The Hobbit (1925)

Gradually, the riddles became darker in nature, and growing tired of the game, Gollum thought the time had come to ask “something hard and horrible,”

This thing all things devours:
Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays kings, ruins town;
And beats high mountain down. [14] [19]

After this round, the questions devolved, and Gollum became determined to eat the hobbit no matter what. But Bilbo, as it happened, had found a magic ring that made him invisible once worn. And after digging in his pocket and placing the ring on his finger, he disappeared. In “a whirl of hope and wonder,” he made a great “leap in the dark” toward the passage that led out of the mines and over the head of the “hissing and cursing” creature who could no longer see him, but dared not follow his prey further away from the dark, slimy lake that was Gollum’s home. The little hobbit had defeated the monster and lived to journey another day. [15] [20]

Each of these victories were, however, somewhat pyrrhic. Oedipus walked over the bones of the many men before him who’d failed the test (and everyone knew what destiny had in store for him); old wrecks littered the sharp rocks of the Sirens’ shore as Odysseus and his men rowed past, and their voices would doubtless wreck many more; the grotesque creatures lurking in the caves of Middle Earth waited for their next chance to devour their prey “raw and wriggling.” And the ring, of course, was an arch-predator that had ensnared a new bearer. Winning the Capital Riddle match held death at bay, but did nothing to foil the long game played by the cruel Fates who always managed to have their way.

Meeting His Match: The Duel

The games men play for sport are actually about war, [16] [21] and the fact that games and riddles seem to have been so deeply appealing to us throughout our history suggests that war, too, is intrinsic to humanity. It might not be hyperbole to argue that “world peace” will forever be a pageant-queen pipe dream, because humans like their riddles and chess boards too much to give them up (and they blur the division between physical and mental competition; war is also a mind game). The next time someone accuses you of treating a serious problem as if it were “just a game,” tell him that games have always been deadly serious affairs. The warrior king in Shakespeare’s Henry V reveled in this type of duel, exalting to his gathered noblemen, “When we have matched our racquets to these balls, / We will in France, by God’s grace, play a set / Shall strike [the French] crown into the hazard!” [17] [22] And in Western history and myth, peers often engaged in wars disguised as riddle-duels: monarch vs. monarch, god vs. titan, priest vs. wise man, Sherlock vs. Moriarty — battle royales with devastating results for one or the other opponent. What are wars, and what are games without great risk and the prospect of glorious reward?

Let’s return to the Bronze Age and the accompanying Classical era of oral poetry and Olympic feats. Chalcas, a Greek seer who had once revealed to Agamemnon that the price of victory against the Trojans would require the sacrifice of Iphigenia (he also prophesied the success of the “Trojan Horse” ruse), forecasted his own eventual death at the hands of a man wiser than himself. Knowing this sobering news, a truly wise man would perhaps have given up riddle games altogether, but like a gunfighter whose passion he lives for and knows he will die for, Chalcas could not quit the combat he loved. One day during his travels through Asia Minor, Chalcas encountered another soothsayer named Mopsos. Both men savored the challenge and fought a verbal duel of question and answer in order to determine who possessed the superior mind. When Mopsos at last claimed victory, the disgraced Chalcas committed suicide and fulfilled his own prophecy.

But the ancient Greeks were not the only early riddlers. In the Norse Vafthrúdnismal, a book in the Eddic saga, Odin matched wits with a powerful giant called the Riddle-Weaver, each of them asking questions of the other, each of their queries one of cosmic significance. “I want to travel and visit Riddle-Weaver,” the All-Father announced, “I want to have a contest about old lore with that wise giant.” [18] [23] And thus arriving disguised at the giant’s great hall, the god put to his host an impertinent challenge: “The first thing I want to know is if you are wise.” [19] [24] Unable to resist such a provocation, the giant agreed to the game, but vowed to kill his visitor should Odin lose their battle. “Who are those young women who fly above the sea, who travel in the air with their craft?”; “How will there still be a sun when the wolf has eaten the one that now flies in the heavens?”; “How did the earth come to be, or heaven? Which was the first?” [20] [25]

After exhausting his store of arcane questions and receiving none but correct answers, Odin posed a final (trick) question: “What did Odin whisper in Balder’s ear, before he placed him on the pyre?” At this, the giant realized that it was the All-Father himself with whom he dealt, and replied humbly, ”No one knows what you said in those ancient days . . . I have spoken my aged wisdom, I have told you of Ragnarok, I have spoken with a doomed mouth,” for “now I know that I wagered my head against Odin’s wisdom.” [21] [26] And so, both parties ended the game with black fate hanging low. The giant accepted the penalty for his defeat, and though Odin escaped with his head still attached, he knew, as the giant had predicted, that it would one day belong to the axe-wielders of Ragnarok.


Arthur Rackham, Odin n’ Sleipnir, ca. 1900

Northern European and Anglo-Saxon stories, in fact, featured many more or less evenly matched riddle-duels. The next example is from Charles Godfrey Leland’s (an American) The Hundred Riddles of the Fairy Bellaria (1892), and the hero in this tale was a heroine. She’d fallen in love with a king whose most treasured possession was his lush garden; any who ventured there without his permission forfeited his life. But the fairy Bellaria wandered onto the grounds anyway and began there to eat of a tree’s fruit. The king caught her, and “thinking she was [only] a woman, said that she must die, unless she answered the question which he should put her.” [22] [28] Obliging, she said, “Put it before your council, that I may be fairly judged.” So he called together all his wise men and asked: ‘‘How many hairs have I on my head?” A lesser being would have scoffed, or been struck dumb, but Bellaria was unafraid. She answered, “Just so many as I have on mine, which is thirty thousand, lacking one. And if thou doubtest it, pull out a hair, and I will pull out one of mine, and so on till all are gone.” Of course, the king was most reluctant to do this, and one among the wise men gave his judgment, Your Majesty, “the maiden is not far from the truth, for it is said that in a full head there are thirty thousand hairs.” [23] [29] And so the King, “seeing that the maiden was wise,” and having become smitten with her beauty, not only spared Bellaria, but married her as well. [24] [30]

Now a queen, Bellaria lived many happy years with her husband and bore him a prince as “beautiful as the sun, moon, and stars.” [25] [31] But trouble soon appeared on their borders, for a wicked king from afar known as Ruggero had resolved to invade their country. Though cruel, King Ruggero was a lover of games, and after hearing of Queen Bellaria’s great wisdom, he put his invasion for the moment aside. Instead, he decided to test her. If she “could answer the hundred riddles which he would put her,” he would do her husband no harm, and would “depart in peace; but that, if she could not answer them, she and her husband [both] should die,” and all their lands would belong to him. [26] [32] These terms were not satisfactory, and because she was a monarch (a magical one) as well, she negotiated a change in their bet. For naught else will I answer your riddles, she declared, unless the contest is “Life for life — thine against mine.” [27] [33] After some grousing, Ruggero agreed and sent her his opening salvo:

“By thy head, O Queen! answer me this riddle: What hast thou often seen fall, but never rise?”

She sang back to him, “The snow which falls upon the plain, as snow doth never rise again.”

“By thy head, O Queen! Answer me this: Who is she who puts on all her clothes when it is hot, and goes naked when it freezes?”

Then the Queen sang to her harp, “The apple tree in summertime, when it is hot, is in her prime, a garment green she then doth wear, and many rustling leaflets bear, but when the winter chills the land, then she is naked as my hand. And to thee, King, I must confess such riddles are not hard to guess.” [28] [34]

The saucy little game went back and forth til Ruggero had asked all one-hundred of his best riddles; admiration of his worthy opponent gave way to terrific anger, and he drew his sword, intending to strike down the fairy queen. But suddenly, “a dizziness seized him, and the evil king fell on his own swordpoint, “which passed straight through his [black] heart.” [29] [35] Is there anything sweeter than besting an arch-rival? Great rejoicing commenced throughout the land, for with little effort the queen had taken the king.

Playing Chase: The Taunt

While riddles intrigue us, there is also something antagonistic about them, an allure that nevertheless irritates. Perhaps this duality has something to do with riddles being a kind of dance-game, often with poetic rhythm and meter, thus giving them a sing-song quality — an insolent taunt, or verbal tag of hide and seek. The “run and chase” impulse from the predator and prey relationship might be the oldest instinct humans have inherited from the primordial ooze. Riddling has always been a means of showmanship, for language can be another form of preening for creatures who lack gaudy feathers and iridescent wings, especially in those cultures that value oratorical prowess (this implies that riddles might also be connected to the mating game many animals play; witty banter is a primary way humans flirt with potential partners). The ability to wield cutting one-liners was more important to King Louis XIV’s courtiers, for instance, than was their skill with the actual rapier-blade hanging from their belts. Indeed, tricksters have used riddles in order to ridicule figures of authority for the perverse thrill of defiance — the adrenaline rush of the chase — and it is to this third form, an inversion of The Trial, that the essay now considers.


An illustration from Beatrix Potter’s The Tale of Squirrel Nutkin (1903)

Children’s books aren’t what they used to be, readers. Why, just the other day I saw a glossy-paged offering entitled Born Ready: The True Story of a Boy Named Penelope prominently featured in a bookstore window. The little troll on the cover sported some kind of blonde afro atop its mulatto head, and the illustrator was someone named “Charnelle.” How we have so rapidly fallen from Goodnight, Moon and The Little Prince to rock-bottom — this will be a riddle future historians will marvel at. Fortunately for the sane portion of the population, we still have (for now, anyway) many classics like Beatrix Potter’s complete works available. Potter was an Englishwoman who wrote children’s stories during the Edwardian era, and her characters were always animals who learned hard lessons the hard way. Her most famous story was Peter Rabbit, but my favorite has always been The Tale of Squirrel Nutkin.

Somewhere in the lovely Lake District, there lived Twinkleberry and his colony of squirrels who every morning rowed their make-shift rafts from their wooded shore to an island in the middle of a large lake. The island was rich in trees and nuts, and one hollow oak housed Old Brown, an owl who was the undisputed head of the island. Having a healthy sense of hierarchy and in order to secure Old Brown’s blessing while they foraged for food, the squirrels would always present him with gifts: sometimes “three fat mice,” other times moles neatly wrapped in leaves and tied round with string. [30] [37] But there was one squirrel who lacked this sense of propriety (and self-preservation): Nutkin, the rude cousin of Twinkleberry.

Instead of politely bowing before Old Brown as he should have done, Nutkin “was excessively impertinent . . . He bobbed up and down like a little red cherry, singing —

Riddle me, riddle me, rot-tottote
A little wee man, in a red red coat!
A staff in his hand, and a stone in his throat;
If you’ll tell me this riddle, I’ll give you a groat. [31] [38]

Twinkleberry and the other squirrels had each brought with them some minnows for Old Brown, but “Nutkin, who had no nice manners, brought no present at all.” He ran ahead of the party, singing —

The man in the wilderness said to me,
“How many strawberries grow in the sea?”
I answered him as I thought good –
“As many red herrings as grow in the wood.” [32] [39]

Old Mr. B! Riddle-me-ree!
Flour of England, fruit of Spain,
Met together in a shower of rain;
Put in a bag tied round with a string,
If you’ll tell me this riddle, I’ll give you a ring!

That last promise “was ridiculous of Nutkin, because he had not got any ring to give to Old Brown.” [33] [40]

But Old Brown, who had an enormous store of patience, it must be said, took no interest in Nutkin’s riddles and chose to ignore the little red squirrel’s antics. This continued day after day: the wise squirrels would bring their offerings, then search for nuts, while Nutkin spent nearly the entire time making a show of himself. Finally, one fine morning Nutkin went too far. After singing his riddle, Nutkin “made a whirring noise” and leapt atop the head of Old Mr. Brown. [34] [41] There was a blur of fur and feathers and then a terrified sqeeeeak! The next thing they knew, the little red squirrels saw Nutkin lodged deep in the pocket of Old Brown, who then took his prey inside the hollow, intending to skin him alive. But by sheer panic and fortune, Nutkin managed to escape the owl’s clutches and launched himself out of Old Brown’s window. In the tumult, however, Nutkin had lost his fine bushy tail. Now if you were to ask him a riddle, the erstwhile troublemaker “will throw sticks at you, and stamp his feet and scold, and shout — ‘Cuck-cuck-cuck-cur-r-r-cuck-k-k!’” [35] [42] Squirrel Nutkin is an excellent lesson for children on the subjects of manners and respect for adults. And of course, the cheeky riddles are also entertaining.

But stories about riddle tricksters taunting the authorities have not always been so humorous, for they have often taken another form: criminals mocking those sent to stop them. The fictional Riddler in Batman’s universe is a well-known example of this phenomenon, but the real Riddlers in our midst have always been much more unnerving. During the late 1960s and early 1970s, the so-called “Zodiac Killer,” a mysterious hooded man who targeted lovers, mailed cryptograms to several San Francisco newspapers. He demanded their publication and claimed that the cracked code would reveal his name. One of the letters remained unsolved for over fifty years, but like the excerpt reprinted below, none answered the riddle of the Zodiac’s identity.

I hope you are having lots of fun in trying to catch me . . .
I am not afraid of the gas chamber
because it will send me to paradice [sic] all the sooner
because I now have enough slaves to work for me
where everyone else has nothing when they reach paradice
so they are afraid of death
I am not afraid because I know that my new life is [sic]
life will be an easy one in paradice death [36] [43]

The Zodiac was a less verbally elegant and much darker version of Squirrel Nutkin, prancing metaphorical circles around both the police and the terrified populace, all while dancing on the graves of his murdered victims.

Neither was the Zodiac the only smartaleck murderer on the loose during this crime-ridden period. Jewish serial killer David Berkowitz, whose modus operandi was shooting at brunette women (and sometimes couples) through their car windows, sent journalists and the NYPD on a merry chase with a series of strange and rambling notes signed: “Son of Sam.” From these, authorities were left to piece together whatever clues and riddles the killer might have purposely or inadvertently left in the text.

Hello from the gutters of N.Y.C. . . . I’m just dropping you a line to let you know that I appreciate your interest in those recent and horrendous .44 killings . . . Tell me Jim, what will you have for July twenty-ninth? . . . Sam’s a thirsty lad and he won’t let me stop killing until he gets his fill of blood . . . don’t think that because you haven’t heard from me for a while that I went to sleep. No, rather, I am still here. Like a spirit roaming the night. Thirsty, hungry, seldom stopping to rest . . . I love my work . . . if I shall be fortunate enough to meet you I will tell you all about Sam if you like and I will introduce you to him. His name is “Sam the terrible.” Not knowing what the future holds I shall say farewell and I will see you at the next job. Or should I say you will see my handiwork at the next job? [37] [44]

What could “Son of Sam” have meant by the date July, the twenty-ninth — clearly a threat? These rambling notes were Capital Riddles, for other deaths were certain to follow should the police fail to solve the enigmas. If they succeeded, “Son of Sam” would end his final moments on the “hot seat.” Catch me if you can!

Asking False Questions: The Trap

But what of those riddles that lack any meaning, that have no answers? These are upsetting, because we are hardwired to always want solutions to our problems; if riddles cry out to be solved, then those without the perfect and elegant missing piece that will satisfy their equations trigger within us a deep sense that something has fundamentally gone wrong. Perhaps the most famous example of such riddles from the Western canon was Lewis Carroll’s Wonderland trilogy, books about a thoroughly mad world down a rabbit hole, or through a looking glass. The protagonist, of course, was a little blonde girl called Alice, and she never shook the feeling of fundamental “wrongness” when wandering the topsy-turvy realm of Wonderland.


“Who cares for you? You’re nothing but a pack of cards!”

As Alice fell, fell, fell down, down, down the rabbit hole, she began to dream: “‘do cats eat bats? Do cats eat bats? And sometimes, ‘Do bats eat cats?’, for you see, as she couldn’t answer either question, it didn’t much matter which way she put it.” [38] [46] It only grew “curiouser and curiouser” from there, for nearly every creature Alice encountered was a nonsense riddler. While attending a mad tea party with the Dormouse, March Hare, and Hatter, Alice attempted to solve the Hatter’s question: “Why is a raven like a writing desk?” At the beginning, the little girl thought, what fun! “I’m glad they’ve begun asking riddles!” [39] [47] But the tea party soon soured, for the Hatter admitted that he had no answer in mind. This “piece of rudeness was more than Alice could bear: she got up in great disgust and walked off.” [40] [48] Further travels took her to the Queen of Hearts’ garden in which several spades and diamonds were exhausting themselves painting white roses red in a vain attempt to please the queen and thus to keep their heads, for it was well-known that the red-faced monarch sent subjects to the chop for nonsense reasons. How to steer clear of her wrath? A riddle not even her husband the King of Hearts could safely answer.

And what to make of this ditty from Through the Looking Glass?

’Twas brillig, and the slithy toves
Did gyre and gimble in the wabe:
All mimsy were the borogoves,
And the mome raths outgrabe.
“Beware the Jabberwock, my son!
The jaws that bite, the claws that catch!
Beware the Jubjub bird, and shun
The frumious Bandersnatch!” [41] [49]

Stuff and nonsense! The answer-less quality of these riddles became riddles themselves; what is the point, after all, of a word problem that has no solution? As one writer for the Guardian put it, “Every one knows how gravely in our dreams we take part in the most absurd transactions,” but Lewis’ ability to translate this unconscious absurdity to the waking hours and onto the page made Wonderland both humorous and unsettling, [42] [50] for it captured the ancient and ongoing conflict between reason and chaos.

William Shakespeare himself was just as enamored of riddles as Lewis Carroll would later be, and his plays often used metaphors, puns, and other word games to entertain his audiences. Othello’s chief villain Iago, the pure essence of chaos, posed a number of cryptic questions to his insecure chief, the effect of which caused the latter to demand answers to the former’s riddles — even as Iago claimed to know “nothing” of it. Indeed, he asked corrupt questions, because he had a corrupt soul:

Iago: Did Cassio, when you wooed my lady [Desdemona] know of your love?
Othello: He did, from first to last. Why dost thou ask?
I: But for a satisfaction of my thought, no further harm.
O: Why of thy thought, Iago?
I: I did not think he had been acquainted with her.
O: O yes, and went between us very oft.
I: Indeed?
O: Indeed? Ay, indeed! Discern’st thou aught in that? Is he not honest?
I: Honest, my lord?
O: Honest–ay, honest.
I: My lord, for aught I know.
O: What dost thou think?
I: Think, my lord?
O: “Think, my lord?” By heaven, thou echo’st me as if there were some monster in thy thought too hideous to be shown. Thou dost mean something.” [43] [51]

These were false riddle-traps set brilliantly and sprung mercilessly in order to drive Othello mad with jealousy and to bring about the demise of nearly every character in the play (including Iago himself). By claiming to “know nothing,” Iago implied that he knew everything. His carefully crafted nonsense played on human fears and the overwhelming impulse we all have: always demand the mystery’s finish, never let a question mark dangle, but obsess over riddles like scorned lovers who refuse to let go.

And the final example of the Western riddle I’ll share is a short story most would not associate with the game, for no riddles were spoken aloud by its characters. Edgar Allan Poe’s “The Mask of the Red Death” took place in an unknown kingdom in an unknown time, but it was certainly a pestilence-savaged land. A disease known as the “Red Death” had swept through Prince Prospero’s country, decimating the population. Those unlucky souls who suffered and died spent their last agonizing moments bleeding from their pores, their faces grotesquely contorted and forever frozen in a red rictus of pain.

Wanting to avoid this fate himself, Prince Prospero, along with a large company of his retainers and nobles, “retired to the deep seclusion of one of his castellated abbeys.” This was an “extensive and magnificent structure, the creation of the prince’s own eccentric yet august taste. A strong and lofty wall girdled it in,” and this wall “had gates of iron. The courtiers, having entered, brought furnaces and massy hammers and welded the bolts.” [44] [52] Such descriptions of heavy velvet-draped, rooms, impregnable fortresses, a maze-like interior (which was itself a riddle), and dark hallways with little light seeping through the window slits instilled in readers a nauseous sense of claustrophobia — of the threat of being buried alive, for the group “resolved to leave means neither of ingress or egress to the sudden impulses of despair or of frenzy from within.” In all “the corridors that followed the suite, there stood, opposite to each window, a heavy tripod, bearing a brazier of fire, that projected its rays through the tinted glass and so glaringly illumined the room. And thus were produced a multitude of gaudy and fantastic appearances.” [45] [53] The party was amply provisioned with fine foods and lavish entertainment: wine, women, and song within, while without, the Red Death.

Contrary to most interpretations of the story, might the Red Death have represented reason and Prospero’s hideaway the chaos? Secluding himself from his subjects who suffered was negligent cowardice — however, it was at least understandable. But throwing balls and indulging in revels that would have shamed Emperor Caligula? The corrupt little group of elites was begging for Fate to set them right, for a comeuppance most terrible. By shirking his duty as ruler, the prince became the representative of chaos and ceded order to Death.

One night during this confinement, Prince Prospero, whose tastes were “bizarre in the extreme,” decided to throw a masqued fête. 46 [54] All wore their ghastly costumes and filtered in and out of seven apartments, no one visible to the other seven in that labyrinth abbey of winding confusion. The thick carpets and heavy drapery muffled their drunken laughter as they circulated like blood through the ventricles of the castle. But suddenly as the clock struck its midnight gong, a stranger appeared. All smiles vanished, and the music scratched off. The figure they saw “was tall and gaunt, and shrouded from head to foot in the habiliments of the grave. The mask which concealed the visage was made . . . to resemble the countenance of a stiffened corpse . . . And yet all this might have been endured, if not approved, by the mad revellers around.” But the fellow “had gone so far as to assume the type of the Red Death. His vesture was dabbled in blood — and his broad brow, with all the features of the face, was besprinkled with the scarlet horror.” [47] [55]

After his initial shock, Prospero demanded that someone seize the foul visitor and unmask him, so that all would know whom they should hang come morning. The prince rushed at the retreating form with a dagger, but having reached “to within three or four feet of [of him],” when the latter, having attained the extremity of the velvet apartment, turned suddenly and confronted his pursuer. There was a sharp cry — and the dagger dropped gleaming upon the sable carpet, upon which, instantly afterwards, fell prostrate in death the Prince Prospero.” It was then that the rest of the party realized that no tangible form existed beneath the stranger’s “grave cerements and corpse-like mask,” but the Red Death himself had stolen into their sanctuary like a thief in the night, “and one by one [they all] dropped, the revellers in the blood-bedewed halls of their revel, and died each in the despairing posture of his fall.” [48] [56] The licking “flames of the tripods expired. And Darkness and Decay and the Red Death held illimitable dominion over all.” [49] [57] Though the prince and his merry friends assumed they’d given Death an impossible Gordian Knot of a riddle to solve, the phantom of the night somehow slipped through their defenses, the riddle of just how he did so never to be solved.

Where do you hide, readers, that he cannot find you? 

Fail to answer, and you will surely die.

*  *  *

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[1] [58] See Marcel Denasi’s The Curious History of the Riddle (New York: Welfleet Press, 2020), 3.

[2] [59] Ibid., 6-7.

[3] [60] See also Johan Huizinga’s Homo Ludens: A Study of the Play-Element in Culture (New York: Roy Publishers, 1950).

[4] [61] See Sophocles’ The Oedipus Plays of Sophocles, trans. Paul Roche (New York: Meridian, 1996).

[5] [62] Homer, The Odyssey, trans. Robert Fagles (New York: Penguin, 1996), 200.

[6] [63] See The Curious History of the Riddle, 14.

[7] [64] Geoffrey Chaucer, The Canterbury Tales, trans. Kent Hieatt and Constance Hieatt (New York: Banam, 1981), 223.

[8] [65] Ibid., 224.

[9] [66] Ibid., 225.

[10] [67] Ibid., 226.

[11] [68] J. R. R. Tolkien, The Hobbit (New York: Houghton Mifflin, 1996), 65.

[12] [69] Ibid., 67.

[13] [70] Ibid., 68-69.

[14] [71] Ibid., 69, 70, 72.

[15] [72] Ibid., 80.

[16] [73] One reason why whites need to quit watching colored people play sports. It’s degrading in a very deep sense to watch blacks play at war with whites.

[17] [74] William Shakespeare, Henry V, 1.4, 262-264.

[18] [75] The Poetic Edda: Stories of the Norse Gods and Heroes, Jackson Crawford, ed. (New York: Hackett, 2015), 48.

[19] [76] Ibid., 49.

[20] [77] Ibid., 52-53.

[21] [78] Ibid., 58-59.

[22] [79] Charles Godfrey Leland, The Hundred Riddles of the Fairy Bellaria (London: T. Fisher Unwin, 1892), 2-3.

[23] [80] Leaving aside baldness, there are actually around 100,000 hairs on the average human head.

[24] [81] Ibid., 2.

[25] [82] Ibid., 3.

[26] [83] Ibid., 3-4.

[27] [84] Ibid., 4.

[28] [85] Ibid., 4-5, 134.

[29] [86] Ibid., 162.

[30] [87] Beatrix Potter, The Tale of Squirrel Nutkin (London: F. Warne & Co., 1903), 17. 

[31] [88] Ibid., 18.

[32] [89] Ibid., 33. 

[33] [90] Ibid., 34.

[34] [91] Ibid., 50.

[35] [92] Ibid., 59.

[36] [93] See the Wikipedia article on the Zodiac [94].

[37] [95] See the Wikipedia article on David Berkowitz [96].

[38] [97] Lewis Carroll, Alice’s Adventures in Wonderland (Ontario: Broadview, 2000), 53.

[39] [98] Ibid., 104.

[40] [99] Ibid., 110.

[41] [100] Lewis Carroll, Through the Looking Glass, freeclassicbooks.com, 9.

[42] [101] Anon., “Alice’s Adventures,” in The Guardian (15 December, 1865).

[43] [102] William Shakespeare, Othello, 3.3, 154-167.

[44] [103] Edgar Allan Poe, “The Masque of the Red Death [104],” 1.

[45] [105] Ibid., 1, 2.

[46] [106] Ibid., 2.

[47] [107] Ibid., 3.

[48] [108] Ibid., 3-6.

[49] [109] Ibid., 6.