11 of the most famous riddles in history

Even 4,000 years ago, people tested one another’s critical thinking skills with riddles and logic puzzles. This ancient civilisation, 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 civilisation 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?”

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.

This riddle isn’t Ancient Sumer old, but it probably dates back to the sixth or eighth century BC. 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.”

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?

Written in the fifth century BC, 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 fulfils 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?”

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.

Here are some more brain teasers that will leave you scratching your head.

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.”

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.” 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.)

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?”

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 riddles that involve lots of numbers are more your thing, try solving these maths puzzles only geniuses can get right.