Folk riddles tend to lack the consequences of literary riddles. The most influential collection of riddles in the Western tradition is perhaps the Aenigmata of Symphosius, which appears in the Latin Anthology of the early sixth-century Codex Salamasianus. Symphosius’ riddles, despite some echoing of Roman poetry, come from the gentler folk tradition and were probably occasional verse for Saturnalia celebrations. T.J. Leary’s recent skilled textual analysis improves the probable dating of the Aenigmata to 368 to 500 AD, but we still have no contemporary extrinsic evidence about the text or the poet’s identity, nationality or intentions.[2]

In the late seventh century Britain’s Saint Aldhelm delighted in Symphosius’ riddles for their intellectual challenges, but criticized them for their lack of a religious underpinning. While he loved the simplicity and intellectual challenges of the genre, he wanted a multitude of ways to bring the glory of the Christian God to Anglo-Saxons—who were not far removed from paganism, if removed at all.

Despite his declared motivation, Aldhelm begins his Aenigmata in a burst of lyric mysticism with six short riddles that lack obvious Christian content.[3] Indeed, the answers for these six riddles feel more pagan than evangelical: earth; wind; cloud; nature; rainbow; moon. Riddle 7 (fate) dispels the mood of this start with its more didactic and literary style. This style often works beautifully as both art and subtle preaching, as in Riddle 49 (cauldron), but sometimes fails by both standards, as in Riddle 99 (camel).

Many Latin poets of Late Antiquity and the early medieval period imitated Aldhelm’s popular Aenigmata, including Tatwine, Eusebius, and Boniface. The more significant riddles inspired by Aldhelm’s Aenigmata are the anonymous late tenth-century Exeter Book riddles. These Old English riddles (our word “riddle” comes from the Old English raedan with a diminutive suffix, which means “to give minor advice”) have received far more scholarly attention than Aldhelm’s Aenigmata—even though many of them are similar to or are paraphrases of Aldhelm’s riddles.

The popularity of the Exeter riddles appears to result in part from manuscript presentation; the Aenigmata typically had an answer above each riddle, whereas the Exeter Book does not include the answers at all. Maddening debate about the “correct” answer eventually created a small academic industry that continues to this day.

Riddles appear in the medieval literature of most of the world, for example in Persia with the poetry of Amir Khusrau (1253-1325). Around 1300 AD the Bohemian Bartholomacus de Solentia (also known as “Doctor Claretus”) displayed an unexpected sympathy for young women with his Latin riddles in which a young girl ably handles a wise old man’s questions—and then turns the tables and stumps him. These riddles probably inspired a popular fairy tale usually called “The Peasant’s Clever Daughter.” Later in the fourteenth century Hajji Khalifa published an important Arabic text on riddles. Around the same time William Langland included a riddle battle in the “Banquet of Conscience” section of Piers Plowman, a probable inspiration for Tolkien’s high-stakes riddle battle between Bilbo and Gollum in The Hobbit.

Interest in riddles surged in the sixteenth century. Thomas Wyatt (1503-1542), sometimes lifting from such Italians as Serafino D’Aquila (1464-1500), loved to riddle; he wrote a nine-line riddle in which the first eight lines all end with the word “not” and the answer is “a kiss.” Lilio Giraldi’s Aenigmata, an influential 1551 text on riddles, helped to create interest in the many Latin riddles of legendary classical scholar Julius Caesar Scaliger (1484-1558). With the liberties of the Renaissance, Scaliger’s puns and sexual humor found a broad audience and helped to return the riddle genre closer to the secular sensibilities of Symphosius.

William Shakespeare (1564-1616) made frequent and creative use of riddles in his plays. For Shakespeare the wit of the answer was not as important as provoking tension or making his audience ponder complexity. In Act III, Scene VI of King Lear the riddling Fool returns to offer this riddle to the King:

Fool: Prithee, Nuncle, tell me whether a madman be a gentleman or a yeoman.

Lear sees the question as applying to him, even though his answer is not one of the choices offered by the Fool:

Lear: A king, a king.

The Fool then provides a different “answer” and avoids direct offense by referring to a “son” rather than three daughters:

Fool: No, he’s a yeoman that has a gentleman to his son; for he’s a mad yeoman that sees his son a gentleman before him.

Lear continues with a vision of damnation, which Edgar reinforces. The Fool, in the manner of a comically exuberant Iago, then sums up with an aphoristic sentence that further reinforces Lear’s paranoia by comparing his daughters to faithless prostitutes:

Lear: To have a thousand with red burning spits
Come hizzing in upon’em—

Edgar: The foul fiend bites my back.

Fool: He’s mad that trusts in the tameness of a wolf, a horse’s health, a boy’s love, or a whore’s oath.

Lear never fully understands the riddling Fool; Shakespeare’s riddles often only present slanted views of the world as it is, and thus they offer more confusion—and dramatic tension—than expected clarity.

Clear answers to riddles are rare throughout Shakespeare’s works. The gravedigger’s self-referential riddle in Hamlet (“What is he that builds stronger than either the mason, the shipwright, or the carpenter?”) has a debatable answer, and seems more targeted at emotions than logic. In Macbeth the riddling prophesies of the Weird Sisters are not answered until it is too late for the characters to understand the riddles’ implications. Again, Shakespeare uses riddles more subtly than his predecessors, and his riddles tend to be aimed more at creating moods, meditations, miscommunications, and misdirection than intellectual epiphanies.

The riddles of the three caskets in The Merchant of Venice are more straightforward than in Macbeth, Hamlet and King Lear, and they echo such riddles as Sophocles’ sphinx riddle where a traveler must answer correctly to get what he wants. In this scene a suitor must pick the correct casket, inscribed with a riddle, to marry Portia. The three choices are:

Gold: Who chooseth me shall gain what many men desire.
Silver: Who chooseth me shall get as much as he deserves.
Lead: Who chooseth me must give and hazard all he hath.
(Act II, Scene VII)

Since the lead casket is the right answer, these riddles screen out the greedy suitors and reward those who understand the commitment of marriage. Similarly, in the opening scene of Pericles, Pericles must answer a riddle to win the hand of King Antiochus’ daughter, but in this case the result is less happy—the riddle confirms what Pericles suspects—that the princess has been committing incest with her father.

Alexander Pope despised riddles, but, as one might expect, his friend Jonathan Swift (1667-1745) adored them and most other forms of wordplay. Many of Swift’s literary friends shared his delight in riddles to the extent that there is some confusion as to which of the riddles should be attributed to Swift and which belong to Delany, Sheridan and other wits of Swift’s circle. His initial plan for publication apparently met with some resistance and Swift eventually published only a small number of riddles.

Some of the opposition seems to have come from the neoclassical poetics of the time, according to which a poem cannot be savored over time once its resolution is fixed. Some may also have objected to Swift’s deviation from the tradition of keeping riddles, like jokes, extremely brief. Swift’s riddles average about thirty-seven lines and “The Gulf of all Human Possessions” runs ninety-six lines—far longer than the longest riddle up until then, Aldhelm’s eighty-three line riddle that concludes his collection. In short, in the collision between the constraints of the genre and Swift’s enthusiasm, the genre prevailed.

The Romantic poets shared Swift’s love of wordplay and literary banter, so it is unsurprising that some of them tried riddling. For Keats (1795-1821) there is linguistic wordplay similar to riddling in many of his poems. Byron (1788-1824) wrote this riddle, which is a classic of misdirection:

The beginning of eternity, the end of time and space,
The beginning of every end, and the end of every place.

After that grandiosity the answer is merely “the letter E.” A similar poem, “A Riddle in the Letter H” (sometimes just called “A Riddle”) is often mistakenly attributed to Byron, but is an imitation by the skilled Catherine Fanshawe (1765-1834).

An inscrutable fragment of William Wordsworth’s (1770-1850) called “Away, away, it is the air…” ends in what seems to be a riddling challenge:

Then tell me if the thing be clear,
The difference betwixt a tear
Of water and of blood.

Samuel Taylor Coleridge (1772-1834) nearly completed a virtually impenetrable riddle, written in English words transliterated into Greek, which seems to describe a much debated event involving Wordsworth, adultery and incest. Recently Adam Roberts skillfully decoded this riddle.[4]

Considering both ambition and quantity, the all-time master of riddles is probably Lewis Carroll (1832-1898). His Phantasmagoria and Other Poems (1869) included a number of riddles, including two that were double acrostics, a feat rarely attempted since Aldhelm’s Praefatio to his Aenigmata. Despite Alice’s disdain for riddles (“I think you might do something better with time than wasting it in asking silly riddles.”), Alice in Wonderland is loaded with riddles and the language of riddles. As with the Exeter Book, scholars have focused on what is unsolved: The Mad Hatter’s riddle “Why is a raven like a writing desk?” Despite a statement by Carroll near the end of his life that indicated that the lack of answer to this riddle was part of his joke, commentators futilely continue to present “solutions” to the raven riddle.

Carroll’s genius for riddles helped to move the public perception of the proper place for riddles from pub and parlor games to fantasy literature of Tolkien and the writers he influenced. The most famous Tolkien riddling occurs in The Hobbit when Bilbo Baggins meets Gollum deep under the Misty Mountains. The two are at a standoff as to how to deal with each other, then enter into an ill-advised pact: if Bilbo wins a riddle battle, Gollum will become his slave, and if Gollum wins, Bilbo will become a meal for Gollum. After five riddles each, Bilbo wins with what appears to be a stroke of luck.

As part of his scholarly pursuits, Tolkien had studied riddles, particularly Norse, Icelandic and Old English riddles, but the riddle battle in the cave is an imaginative expansion of Sophocles’ riddle of the sphinx where intellect substitutes for physical force. No poet had ever brought tension and drama into riddles the way that Tolkien did in this ten-riddle match for life and freedom. Late in the book Tolkien used Bilbo’s riddles with Smaug the dragon to similar effect. Tolkien was also impressively inventive when he had Gandalf the wizard respond to a simple greeting by Bilbo as if he had been posed a riddle; the comic relief of that exchange is Shakespearian in character.

Wordplay is central to J.K. Rowling’s Harry Potter books—they abound with anagrams, portmanteaus (a coinage of Lewis Carroll), puns and verbal parallels as hints of character. Riddles matter too—the phrase “I am Lord Voldemort” is an anagram of the fallen angel’s original name, “Tom Marvolo Riddle.” In Harry Potter and the Goblet of Fire, Rowling revives Sophocles’ sphinx, who will not let Harry pass until he answers a three-part riddle that requires that each answer for each part then be combined phonetically in order to achieve the actual answer necessary to satisfy the sphinx. Similarly, in Harry Potter and the Philosopher’s Stone Hermione solves Snape’s mind-bendingly complex riddle in order to enter the room where the Philosopher’s Stone is housed.

Poets of our time and the recent past have also had an interest in riddles. Richard Wilbur (1921-2017) rendered exquisite translations of Symphosius’ one hundred riddles. He also wrote his own “Riddle,” which appears to be a brief devotional poem in which Wilbur himself is a riddle for God imagined as a writer—but it then takes a wry turn in the final line.

Sylvia Plath (1932-1963) wrote a riddle called “Metaphor” which, like Wilbur’s “Riddle,” focuses on herself as a riddle. It begins by laying out a poem written in nine-syllable syllabic lines—a meter that is similar to iambic pentameter in its line length, but edgier due to the unpredictability of its stresses:

I’m a riddle in nine syllables.

We do not know that Plath was writing while pregnant, but “nine” in the first line is a hint. Plath continues with the same pattern metrically, but then resists the order implied by rhyme as she offers a series of metaphors for her condition that begin:

An elephant, a ponderous house,
A melon strolling on two tendrils.

Metaphors humorously lamenting her condition continue, until the last line, where, like Wilbur, she turns the poem in an unexpected direction. Predictably in hindsight, Wilbur can end with humor and a feeling of grace, whereas Plath plunges the reader into her despair:

I’ve eaten a bag of green apples,
Boarded the train there’s no getting off.

As with many of Shakespeare’s riddles, Plath resists offering us a clean answer to the “What am I?” question. While superficially clear—she’s pregnant—what is left unsaid in the riddle invites the reader to fill that void with the feelings of dread and regret that Plath feels.[5]

Jokes and riddles share similar linguistic structures. Both start with a question. Some modern jokes may seem not to start in that fashion, but typically such jokes imply a question. If the apparent opening line of the joke is in the form of a statement along the lines of “A horse walks into a bar…”, the speaker is invariably posing this implied question: “What happens when a horse walks into a bar?”

For good jokes and riddles, silence—often awkward silence—follows the question. After this silence, the listener expects an answer that follows from the facts provided in the riddle or joke. There, however, the similarities end. The audience for a joke laughs if the joke is a good one. The words of the joke shift the perspective of the audience in ways that makes us see some absurdity in life—whether through wordplay, undermining of a social convention, a disruption of expectation, or some other subversive technique.

Riddles try to make you see the world as it is, and thus are not inherently subversive in the ways that jokes are. Riddles rarely provoke the same reaction as a joke—a wry smile or the grimace of learning the correct answer in a crossword puzzle, perhaps, but not hilarity. Riddles are only subversive when truth itself is subversive or when they are included in another text and “the answer” provides some tension with the narrative—Shakespeare was a master of that technique.

Scholars have written some outstanding books about certain types of riddles—Adam Roberts’ The Riddles of The Hobbit (Palgrave MacMillan, 2013) and Dieter Bitterli’s Say What I Am Called (University of Toronto Press, 2009) to name just a few—but it remains true that the academy tends to ignore riddles and their uses. As a result, we lack both a widely accepted definition of a riddle and a comprehensive perspective on riddles across time and cultures.