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11 of History's Toughest Riddles

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1. A HOBBIT HEAD SCRATCHER

Anyone who’s gotten lost in Middle Earth knows that J.R.R. Tolkien loved a logic puzzle. The riddle competition between Bilbo Baggins and Gollum in The Hobbit serves up several mind-bending morsels, the trickiest of which might be:

Voiceless it cries,
Wingless flutters,
Toothless bites,
Mouthless mutters.

Answer: The wind

2. THE MAD HATTER'S DIRTY TRICK

One of the most famous literary riddles in literature is also the most frustrating ... because it came without an answer! In Alice's Adventures in Wonderland, the Mad Hatter poses this puzzle to Alice:

“Why is a raven like a writing desk?”

Answer: The Hatter doesn’t have the answer, and as it turns out, Carroll didn’t, either. But readers’ desire for closure was so intense that the author was forced to dream up an answer that later appeared in a preface:

Enquiries have been so often addressed to me, as to whether any answer to the Hatter's Riddle can be imagined, that I may as well put on record here what seems to me to be a fairly appropriate answer, viz: 'Because it can produce a few notes, tho they are very flat; and it is never put with the wrong end in front!' This, however, is merely an afterthought; the Riddle, as originally invented, had no answer at all.”

3. OEDIPUS'S COMPLEX PROBLEM

In Sophocles’ Oedipus Rex, the title character must answer to the Sphinx to save his own life and continue his journey to Thebes. Spoiler: he nails it. The monster asks: 

What walks on four feet in the morning, two in the afternoon and three at night? 

Answer: “Man: as an infant, he crawls on all fours; as an adult, he walks on two legs and; in old age, he uses a 'walking' stick.” 

4. A HARRY POTTER PUZZLER

The Harry Potter series is teeming with playful language and cleverness, so it’s only right that a juicy riddle made its way into the series. In The Goblet of Fire, J.K. Rowling gives a nod to the Sphinx by putting one in the maze during the Triwizard Tournament. Harry is tasked with cracking this 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?

Answer: A spider.

5. GUARDED TRUTHS

The riddle was coined by mathematician Raymond Smullyan and goes by many names—“A Fork in the Road,” “Heaven and Hell,” and “The Two Doors,” among them. It is probably most well known for having a role in the 1986 movie Labyrinth. Here’s the basic idea: You’re met with a choice between two identical doors with an identical guard at each. One door leads to heaven and one door leads to hell. You can ask one guard one question and then make your choice on which door to pass through. One of the guards always tells the truth and one of them always lies. So, what question do you ask? 

Answer: In Labyrinth, the protagonist (Sarah, played by Jennifer Connelly) gets it right. She asks the one on the left, “Would he [referencing the guard on the right] tell me that this door leads to the castle?” Leftie tells Sarah yes, and from there, she is able to conclude that he is the one guarding the door to “certain death.” This can get tricky to work through, but luckily the Internet has an unending supply of resources if you want a deep dive into the puzzle’s logic.

6. A BULLY RIDDLE

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This riddle was rumored to be Teddy Roosevelt’s favorite: 

I talk, but I do not speak my mind
I hear words, but I do not listen to thoughts
When I wake, all see me
When I sleep, all hear me
Many heads are on my shoulders
Many hands are at my feet
The strongest steel cannot break my visage
But the softest whisper can destroy me
The quietest whimper can be heard.

Answer: An actor 

7. JAMES JOYCE GOES DEEP

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In Ulysses, Stephen Dedalus poses a riddle to his pupils. A word to the wise: don’t spend too much time trying to work this one out. 

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

Answer: “The fox burying his grandmother under a hollybush.” 

Get it? Dedalus’s students don’t, and many scholars believe that’s sort of the point. The exaggerated difficulty is meant to be a kind of riddle about riddles.

However, not all of Joyce’s riddles in Ulysses are impossible. Protagonist Leopold Bloom jokes, "Good puzzle would be cross Dublin without passing a pub.” This equally baffling head scratcher was solved by a software developer in 2011. The programmer managed to map all of Dublin’s pubs and used an algorithm to chart a course that never comes within 115 feet of one.

8. THE ONE THAT STARTED IT ALL

There is debate over who wrote the first riddle, but the ancient civilization of Sumer is certainly responsible for one of them. Sumerians’ contribution to the legacy of logic problems: 

There is a house. One enters it blind and comes out seeing. What is it?

Answer: A school

9. THINK HARD

Another oldie-but-goodie originated in 18th century England, though you might know it from Die Hard with a Vengeance.

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?

Answer: One. As John McClane learns, this is a classic trick question. If the narrator meets the group on the way to St. Ives, then they must be going in the opposite direction and the math calculations are simply a bit of trickery meant to misdirect.

10. PLATO’S ANCIENT HEAD-SCRATCHER

In The Republic, the philosopher Plato makes reference to a famous Greek riddle credited to someone named Panarces:

There is a story that a man and not a man

Saw and did not see a bird and not a bird

Perched on a branch and not a branch

And hit him and did not hit him with a rock and not a rock.

Answer: “A eunuch who did not see well saw a bat perched on a reed and threw a pumice stone at him which missed,” according to Plato. You can be forgiven for not coming up with that off the top of your head. In Greek, the verb for “to hit” can also indicate throwing something with the intention of hitting it.

11. EINSTEIN’S FISHY PUZZLE

The so-called “Eistein’s Riddle” asks a simple question: “Who owns the fish?” It may not have been written by Einstein—sometimes it’s attributed to Lewis Carroll, and it’s highly likely that neither of them wrote it at all. Occasionally, some versions feature other animals, like zebras, instead of fish. But regardless of its origins, this riddle is a tough one:

Here’s the set-up:

There are 5 houses in five different colors.

In each house lives a person with a different nationality.

These five owners drink a certain type of beverage, smoke a certain brand of cigar and keep a certain pet.

No owners have the same pet, smoke the same brand of cigar or drink the same beverage.

The question is: Who owns the fish?

These are your hints:

The Brit lives in the red house

The Swede keeps dogs as pets

The Dane drinks tea

The green house is on the left of the white house

The green house's owner drinks coffee

The person who smokes Pall Mall rears birds

The owner of the yellow house smokes Dunhill

The man living in the center house drinks milk

The Norwegian lives in the first house

The man who smokes blends lives next to the one who keeps cats

The man who keeps horses lives next to the man who smokes Dunhill

The owner who smokes BlueMaster drinks beer

The German smokes Prince

The Norwegian lives next to the blue house

The man who smokes blend has a neighbor who drinks water.

Answer: The German. Here's an explanation.

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The Real Bay of Pigs: Big Major Cay in the Bahamas
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When most people visit the Bahamas, they’re thinking about a vacation filled with sun, sand, and swimming—not swine. But you can get all four of those things if you visit Big Major Cay.

Big Major Cay, also now known as “Pig Island” for obvious reasons, is part of the Exuma Cays in the Bahamas. Exuma includes private islands owned by Johnny Depp, Tyler Perry, Faith Hill and Tim McGraw, and David Copperfield. Despite all of the local star power, the real attraction seems to be the family of feral pigs that has established Big Major Cay as their own. It’s hard to say how many are there—some reports say it’s a family of eight, while others say the numbers are up to 40. However big the band of roaming pigs is, none of them are shy: Their chief means of survival seems to be to swim right up to boats and beg for food, which the charmed tourists are happy to provide (although there are guidelines about the best way of feeding the pigs).

No one knows exactly how the pigs got there, but there are plenty of theories. Among them: 1) A nearby resort purposely released them more than a decade ago, hoping to attract tourists. 2) Sailors dropped them off on the island, intending to dine on pork once they were able to dock for a longer of period of time. For one reason or another, the sailors never returned. 3) They’re descendants of domesticated pigs from a nearby island. When residents complained about the original domesticated pigs, their owners solved the problem by dropping them off at Big Major Cay, which was uninhabited. 4) The pigs survived a shipwreck. The ship’s passengers did not.

The purposeful tourist trap theory is probably the least likely—VICE reports that the James Bond movie Thunderball was shot on a neighboring island in the 1960s, and the swimming swine were there then.

Though multiple articles reference how “adorable” the pigs are, don’t be fooled. One captain warns, “They’ll eat anything and everything—including fingers.”

Here they are in action in a video from National Geographic:

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Photo Illustration by Lucy Quintanilla. Balloon/Poe, iStock
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History
When Edgar Allan Poe Pranked New York City—And Inspired Jules Verne
Photo Illustration by Lucy Quintanilla. Balloon/Poe, iStock
Photo Illustration by Lucy Quintanilla. Balloon/Poe, iStock

On April 13, 1844, a special extra of the New York Sun announced: “ASTOUNDING NEWS! … THE ATLANTIC CROSSED IN THREE DAYS! SIGNAL TRIUMPH OF MR. MONCK MASON’S FLYING MACHINE!!!” According to the article, a balloon heading from England toward Paris had been blown off-course and landed safely near Charleston, South Carolina. The “report” was submitted by a journalist who was also a well-known short-story writer: Edgar Allan Poe.

There was just one problem. He had made the whole thing up.

“The Balloon Hoax,” as it later became known, was Poe’s idea of a calling card. He had just moved to Manhattan, looking for work as a journalist. What better way to announce you’ve arrived than to prank an entire city?

The possibility of balloon travel had ignited the popular imagination since the 1780s, when the Montgolfier brothers built the first balloon to carry a man into the air. By the 1830s, balloonists had successfully crossed the British Channel, and they had begun talking about attempts to cross the Atlantic in earnest.

Newspapers were often full of the exploits of daring aeronauts, and the interest in ballooning apparently led to some fictional takes on the pursuit. Poe’s story in The Sun wasn’t the first: In 1835, Richard Adams Locke published a widely credited account of a balloon reaching the moon. The success infuriated Poe, who had just two months earlier published a story about a man returning from the moon in a balloon, “Hans Pfaall—A Tale.” Poe was certain Locke had plagiarized him, but Locke received all the glory for his “Moon Hoax.” (Ironically, Poe’s own hoax included long sections from the aeronaut Thomas Monck Mason’s 1836 account of his balloon voyage from England to Germany.) Poe decided he would do a little self-promotion while outdoing his old enemy: He submitted the hoax to the same paper that had published Locke’s. The paper published the account with glee, completely unaware that it was fake.

According to Poe's report, a balloon called the Victoria held eight people and made the crossing in 75 hours. At the time, it took two weeks to cross the Atlantic by boat, so the potential for a voyage in which “the broad Atlantic becomes a mere lake,” as one of the passengers supposedly remarked, created quite a stir. Poe later claimed that when the Sun first announced the special Extra with details of the fantastic voyage, “the whole square surrounding the Sun building was literally besieged … I never witnessed more intense excitement to get possession of a newspaper. As soon as copies made their way into the streets, they were bought up, at almost any price, from the newsboys.”

Poe included an abundance of scientific detail to give the article an air of authority, from precise measurements of key components, down to the screws and steel wires, to the combined weight of the fictional passengers (1200 pounds). His main characters were also based on real people: Poe named the pilot after Monck Mason, the famed aeronaut whose accounts he had liberally borrowed from.

The report was picked up in the next day's New York Sunday Times (no connection to The New York Times, which had yet to be founded) and Baltimore Sun. Other papers were less convinced of the report's veracity, and seemed to realize that further news should have come up from Charleston. (One contemporary account suggests that Poe himself revealed the hoax by drunkenly boasting about it in front of the crowd at the newspaper’s headquarters.)

Two days after the hoax first appeared, the New York Sun published a retraction. "The mails from the South last Saturday night not having brought a confirmation of the arrival of the Balloon from England ... we are inclined to believe that the intelligence is erroneous," the paper said. However, they added, "We by no means think such a project impossible." Astoundingly, balloonists would not truly accomplish a trans-Atlantic flight until 1978.

Poe believed his little trick would demonstrate his mastery of scientific description and artful writing. He was so assured of his skill, he didn’t seem to realize that publishing known misinformation would hurt his chances of finding work as a journalist—which is exactly what happened.

But the hoax did inspire someone else: Jules Verne later read it and began working on the adventure that would first bring him fame, Five Weeks in a Balloon, published in 1863. That tale was an immediate success, earning him the financial independence that would allow him to go on to write blockbusters such as A Journey to the Center of the Earth and Around the World in Eighty Days. Whether Poe would have appreciated Verne’s achievements, so heavily influenced by his own work, is another matter.

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