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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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Big Questions
Why Do Cats 'Blep'?
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As pet owners are well aware, cats are inscrutable creatures. They hiss at bare walls. They invite petting and then answer with scratching ingratitude. Their eyes are wandering globes of murky motivations.

Sometimes, you may catch your cat staring off into the abyss with his or her tongue lolling out of their mouth. This cartoonish expression, which is atypical of a cat’s normally regal air, has been identified as a “blep” by internet cat photo connoisseurs. An example:

Cunning as they are, cats probably don’t have the self-awareness to realize how charming this is. So why do cats really blep?

In a piece for Inverse, cat consultant Amy Shojai expressed the belief that a blep could be associated with the Flehmen response, which describes the act of a cat “smelling” their environment with their tongue. As a cat pants with his or her mouth open, pheromones are collected and passed along to the vomeronasal organ on the roof of their mouth. This typically happens when cats want to learn more about other cats or intriguing scents, like your dirty socks.

While the Flehmen response might precede a blep, it is not precisely a blep. That involves the cat’s mouth being closed while the tongue hangs out listlessly.

Ingrid Johnson, a certified cat behavior consultant through the International Association of Animal Behavior Consultants and the owner of Fundamentally Feline, tells Mental Floss that cat bleps may have several other plausible explanations. “It’s likely they don’t feel it or even realize they’re doing it,” she says. “One reason for that might be that they’re on medication that causes relaxation. Something for anxiety or stress or a muscle relaxer would do it.”

A photo of a cat sticking its tongue out
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If the cat isn’t sedated and unfurling their tongue because they’re high, then it’s possible that an anatomic cause is behind a blep: Johnson says she’s seen several cats display their tongues after having teeth extracted for health reasons. “Canine teeth help keep the tongue in place, so this would be a more common behavior for cats missing teeth, particularly on the bottom.”

A blep might even be breed-specific. Persians, which have been bred to have flat faces, might dangle their tongues because they lack the real estate to store it. “I see it a lot with Persians because there’s just no room to tuck it back in,” Johnson says. A cat may also simply have a Gene Simmons-sized tongue that gets caught on their incisors during a grooming session, leading to repeated bleps.

Whatever the origin, bleps are generally no cause for concern unless they’re doing it on a regular basis. That could be sign of an oral problem with their gums or teeth, prompting an evaluation by a veterinarian. Otherwise, a blep can either be admired—or retracted with a gentle prod of the tongue (provided your cat puts up with that kind of nonsense). “They might put up with touching their tongue, or they may bite or swipe at you,” Johnson says. “It depends on the temperament of the cat.” Considering the possible wrath involved, it may be best to let them blep in peace.

Have you got a Big Question you'd like us to answer? If so, let us know by emailing us at bigquestions@mentalfloss.com.

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Afternoon Map
The Most Popular Infomercial Product in Each State

You don't have to pay $19.95 plus shipping and handling to discover the most popular infomercial product in each state: AT&T retailer All Home Connections is giving that information away for free via a handy map.

The map was compiled by cross-referencing the top-grossing infomercial products of all time with Google Trends search interest from the past calendar year. So, which crazy products do people order most from their TVs?

Folks in Arizona know that it's too hot there to wear layers; that's why they invest in the Cami Secret—a clip-on, mock top that gives them the look of a camisole without all the added fabric. No-nonsense New Yorkers are protecting themselves from identity theft with the RFID-blocking Aluma wallet. Delaware's priorities are all sorted out, because tons of its residents are still riding the Snuggie wave. Meanwhile, Vermont has figured out that Pajama Jeans are the way to go—because who needs real pants?

Unsurprisingly, the most popular product in many states has to do with fitness and weight loss, because when you're watching TV late enough to start seeing infomercials, you're probably also thinking to yourself: "I need to get my life together. I should get in shape." Seven states—Colorado, Idaho, Kentucky, Montana, Nebraska, Utah, and Wisconsin—have invested in the P90X home fitness system, while West Virginia and Arkansas prefer the gentler workout provided by the Shake Weight. The ThighMaster is still a thing in Illinois and Washington, while Total Gym and Bowflex were favored by South Dakota and Wyoming, respectively. 

Kitchen items are clearly another category ripe for impulse-buying: Alabama and North Dakota are all over the George Forman Grill; Alaska and Rhode Island are mixing things up with the Magic Bullet; and Floridians must be using their Slice-o-matics to chop up limes for their poolside margaritas.

Cleaning products like OxiClean (D.C. and Hawaii), Sani Sticks (North Carolina), and the infamous ShamWow (which claims the loyalty of Mainers) are also popular, but it's Proactiv that turned out to be the big winner. The beloved skin care system claimed the top spot in eight states—California, Mississippi, Nevada, New Mexico, Oklahoma, Oregon, Tennessee, and Texas—making it the most popular item on the map.

Peep the full map above, or check out the full study from All Home Connections here.

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