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11 of the Most Famous Riddles in History

From the Bible to Shakespeare to Harry Potter, these riddles were dreamed up by some of history’s most celebrated writers—and puzzled some of its most famous characters.

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Ancient Sumer: The world’s oldest riddle

Even 4,000 years ago, people tested one another’s critical thinking skills with riddles and logic puzzles. This ancient civilization, located in what is today the country of Iraq, left us with one of the earliest known examples of a written riddle. (Ancient Sumer is also the civilization with the oldest surviving writing system that we know of!) Here is the riddle: “There is a house. One enters it blind and comes out seeing. What is it?”

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A school. The Sumerians placed a significant emphasis on the value of education and knowledge, and some of their mathematical discoveries are still in use today. Learn about some of the strangest unsolved mysteries of the ancient world.

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The Bible: Samson’s riddle

This riddle isn’t Ancient Sumer old, but it probably dates back to the sixth or eighth century B.C. In the Book of Judges, the seventh book in the Old Testament, Samson poses a riddle to his 30 dinner guests. He tells them that if they answer correctly, he will give them 30 expensive pieces of clothing, but if they guess wrong, they must give him expensive clothing. The catch? The riddle was rigged. The guests wouldn’t have known the answer because only people who knew Samson personally had any hope of solving it. So you certainly shouldn’t break your brain trying to figure it out, but here it is all the same: “Out of the eater, something to eat; out of the strong, something sweet.”

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Bees making a honeycomb inside the carcass of a lion. Sometime before the feast, Samson had killed a lion with his bare hands, and returned to find bees building a hive inside the lion’s body. “The eater” and “the strong” are both the lion, and the”something to eat” and “the sweet” are the honey. Can you see why Samson’s guests felt cheated? An MIT professor called this “the hardest logic puzzle ever.” Can you solve it?

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Sophocles: The Sphinx’s riddle

Written in the fifth century B.C., Oedipus the King is one of the most famous pieces of literature of all time, so it makes sense that it gave us one of the most famous riddles of all time. In this tragic story of Oedipus, who fulfills his destiny even as he’s trying to avoid it, one of the happier moments comes when the title character solves the Sphinx’s riddle. With the head of a woman and the body of a lion, the monstrous Sphinx stood guard at the gates of the city of Thebes. She would tell every traveller a riddle, and would let them pass if they got it right, but would make a meal of them if they got it wrong. Despite these high stakes, Oedipus got the riddle right: can you? “What goes on four legs in the morning, on two legs at noon, and on three legs in the evening?”

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A human. Humans crawl on hands and knees (“four legs”) as a baby, walk on two legs in mid-life (representing “noon,”) and use a walking stick or cane (“three legs”) in old age. If you can solve this puzzle, you could qualify to be a British spy.

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William Shakespeare: The Riddle of Venice

This isn’t a riddle for Shakespeare’s readers to solve, but rather one that tricked some of his characters. In the Bard’s famous comedy The Merchant of Venice, the father of the young heiress Portia concocts a puzzle to ensure that his daughter marries a worthy suitor. He requires that any suitor must choose one of three caskets: one casket is gold, one is silver, and one is made of lead. One casket has a photo of Portia inside it, and only the suitor who chooses that casket may marry her. Here are the clues the suitors must use to decide:

  • On the gold casket: “Who chooseth me shall gain what many men desire.”
  • On the silver casket: “Who chooseth me shall get as much as he deserves.”
  • On the lead casket: “Who chooseth me must give and hazard all he hath.”
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The lead casket contains Portia’s picture. The first suitor opens the gold casket, only to find a skull inside and a note reading “All that glisters [glitters] is not gold,” warning him that valuing things only by their beauty is a mistake. The suitor who chooses the silver casket finds only a picture of a fool, “what he deserves” since he must be a fool to think he was automatically “deserving” of Portia’s hand. The note inside this one reads: “With one fool’s head I came to woo, / But I go away with two.” (Ouch—Shakespearean insults at their finest!) Finally, the suitor who chooses the lead casket is betrothed to Portia. Since the riddle said that the chooser of lead “must give and hazard all he hath,” Portia’s father knows that this man will be willing to make sacrifices and work hard at the marriage. And it just so happens that this lucky suitor is also the man Portia herself is in love with, and they live happily ever after. (The Merchant of Venice is one of Shakespeare’s happier works.) Believe it or not, these 21 everyday phrases were invented by Shakespeare.

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Eighteenth-century England: A riddle with a vengeance

This riddle, known as “As I was going to St. Ives,” began as a nursery rhyme in the seventeenth century. St. Ives is a fishing town in Cornwall. Though its earliest appearance was in a 1730 manuscript, it’s most famous for its appearance in the Die Hard threequel, Die Hard With a Vengeance. The villain asks Bruce Willis and Samuel L. Jackson to solve it in 30 seconds or a bomb will go off on a crowded city block. Now that’s an enduring riddle: one that went from a children’s rhyme to an action blockbuster. It goes like this:

“As I was going to St. Ives,
I met a man with seven wives,
Each wife had seven sacks,
Each sack had seven cats,
Each cat had seven kits:
Kits, cats, sacks, and wives,
How many were there going to St. Ives?”

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One. The answer, which Samuel L. Jackson figures out at the last second, is only one person. This riddle is something of a trick question, throwing all of those sevens in there to make you think you have to do lots and lots of multiplication. But in reality, the speaker was going to St. Ives when he met the polygamous gang, so they all must have been returning from St. Ives, not going. If quizzes are more your thing, try solving these 10 trivia questions only geniuses can get right.

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Jane Austen: Emma’s riddle

In Austen’s 1815 novel Emma, the title character outwits a mercenary suitor when she successfully solves his riddle. Think of this one in two parts, and, for another hint, think of what the suitor is doing.

“My first displays the wealth and pomp of kings,
Lords of the earth! their luxury and ease.
Another view of man, my second brings,
Behold him there, the monarch of the seas!”

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Courtship. The first part, which “displays the wealth and pomp of kings,” represents the “court” part of the word, and the second part, “the monarch of the seas,” is the “ship.” This fictional riddler sure was feeling confident, attempting to court a woman with a riddle about courtship. It doesn’t work in his favour, though, since Emma both beats his riddle and turns down his proposal. Fun fact: Did you know Jane Austen’s fans were called Janeites?

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Lewis Carroll: Alice’s Riddle in Wonderland

Alice’s Adventures in Wonderland, published in 1865, is chock-full of nonsense, and this riddle is no exception. When Alice is at the Mad Tea Party, the Hatter himself asks this perplexing question. Riddle-solvers, beware: don’t expect a straight answer from anyone in Wonderland. “Why is a raven like a writing desk?”

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The Mad Hatter hasn’t the slightest idea, and neither do we. This riddle is famous because of its lack of an answer: when Alice gives up and asks for the answer, the Hatter says, “I haven’t the slightest idea!” He was asking a question, not telling a riddle. Carroll even admitted that he himself hadn’t thought of an answer. However, readers pestered him so much about it that he eventually came up with one. In a preface to a later edition of Wonderland, he wrote, “because it can produce a few notes, though they are very flat; and it is never put with the wrong end in front!” The nineteenth-century puzzle expert Sam Loyd thought of another response: “because Poe wrote on both,” referencing Edgar Allan Poe’s celebrated work The Raven. Are numbers riddles more your thing? Try solving this tricky numbers riddle in less than 60 seconds!

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Albert Einstein: A fishy riddle

While this isn’t a literary riddle, it’s certainly gone down in history as one of the most famous ever because of its supposed creator: Albert Einstein. Though it’s never been outright proven that a young Einstein created this riddle, legend has it that he did—and that he predicted that only two per cent of people would be able to crack it. In our opinion, Einstein should’ve had a little more faith in people: the puzzle is totally solvable if you can use logic to work your way through the clues! Here are those clues:

There are five houses in a row. Each house is painted a different colour and has a person of a different nationality living in it. Each person drinks a different beverage, smokes a different type of cigar, and owns a different animal as a pet. Using these 15 clues, which person owns the pet fish?

  1. The Brit lives in the red house.
  2. The Swede has a pet dog.
  3. The Dane drinks tea.
  4. The green house is directly to the left of the white house.
  5. The person in the green house drinks coffee.
  6. The person who smokes Pall Mall has a pet bird.
  7. The person in the yellow house smokes Dunhill cigars.
  8. The person in the center house drinks milk.
  9. The Norwegian lives in the first house.
  10. The person who smokes Blends lives next to the person with the pet cat.
  11. The person with the pet horse lives next to the one who smokes Dunhill.
  12. The person who smokes BlueMaster drinks beer.
  13. The German smokes Prince.
  14. The Norwegian lives next to the blue house.
  15. The person who smokes Blends has a neighbour who drinks water.
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The German owns the fish. To figure this one out, try making a chart showing each house and filling out the information as you deduce it. Check out our full breakdown of Einstein’s riddle—including a detailed video showing how to find the answer. It turns out Albert Einstein also revealed the secret to happiness—and it’s genius!

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Ulysses: A riddle among riddles

This stumper comes from James Joyce’s twentieth-century behemoth of a novel, Ulysses. Stephen Dedalus, the character who is supposed to represent Joyce himself, is teaching a class on Roman history and poses a riddle to his students. The answer is so specific, and the fictional students so confused, that most scholars who read Ulysses come to the conclusion that Joyce was poking fun at riddles and at people who take them way too seriously. Here it is:

“The cock crew,
The sky was blue:
The bells in heaven
Were striking eleven.
‘Tis time for this poor soul
To go to heaven.”

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“The fox burying his grandmother under a hollybush.” If you’re scratching your head right now, well, that’s almost definitely what Joyce wanted. As Don Gifford puts it in “Notes for Joyce,” this is a riddle that “is unanswerable unless the answer is already known.” Here are 14 more famous books you really should have read by now.

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The Hobbit: Gollum’s final riddle

In this 1937 precursor to The Lord of the Rings, Bilbo Baggins, the titular Hobbit, finds himself riddle-solving for his life to escape from the underground lair of the evil Gollum. Gollum tells Bilbo he’ll grant him safe passage if he solves five separate riddles, the last of which is this:

“This thing all things devours;
Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays king, ruins town,
And beats mountain down.”

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Time. Bilbo solves every other riddle correctly, but with this one, he’s just lucky. Asking for Gollum to give him more time to solve it, he blurts out the word “time”… which is the correct answer! Don’t miss these nine overrated classics—and the better books you should be reading instead!

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Harry Potter and the Goblet of Fire: The other Sphinx’s riddle

In the fourth instalment of the Harry Potter series, the young wizard must take part in the Triwizard Tournament, a dangerous magical competition. For the final task, he has to make his way through an obstacle-filled maze. One of the obstacles is a Sphinx who won’t let Harry pass until he solves her riddle. JK Rowling, of course, was showing off her substantial knowledge of literary history by having a Sphinx, one of the most famous riddle-tellers in literature, be the magical creature to test Harry’s riddling skills. Here’s the wizard-worthy puzzle:

“First think of the person who lives in disguise,
Who deals in secrets and tells naught but lies.
Next, tell me what’s always the last thing to mend,
The middle of middle and end of the end?
And finally give me the sound often heard
During the search for a hard-to-find word.
Now string them together, and answer me this,
Which creature would you be unwilling to kiss?”

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A spider. This one essentially has three parts. The first, the liar in disguise, is a spy. The last thing in the word “mend,” which also appears at the middle of “middle” and ends the word “end,” is the letter D. And finally, “er” is the puzzled sound referenced in the third part of the clue. Once you’ve solved the three mini-clues (or only two, as Harry does), the riddle becomes a rebus puzzle, and you have to put the three parts together to form the answer: “spy-d-er.” Harry successfully solves the first and third parts, then puts them together and realizes that the unkissable creature must be a spider. The Sphinx lets him pass, and then moments later, Harry encounters a real giant spider in the same maze. So this riddle doubled as a warning. Here are 22 Harry Potter jokes every Muggle should know!

[Sources: HuffPost, Mental Floss]

Reader's Digest
Originally Published on Reader's Digest