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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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A Hamilton-Themed Cookbook is Coming
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Hamilton Broadway

Fans of Broadway hit Hamilton will soon be able to dine like the Founding Fathers: As Eater reports, a new Alexander Hamilton-inspired cookbook is slated for release in fall 2017.

Cover art for Laura Kumin's forthcoming cookbook
Amazon

Called The Hamilton Cookbook: Cooking, Eating, and Entertaining in Hamilton’s World, the recipe collection by author Laura Kumin “takes you into Hamilton’s home and to his table, with historical information, recipes, and tips on how you can prepare food and serve the food that our founding fathers enjoyed in their day,” according to the Amazon description. It also recounts Hamilton’s favorite dishes, how he enjoyed them, and which ingredients were used.

Recipes included are cauliflower florets two ways, fried sausages and apples, gingerbread cake, and apple pie. (Cue the "young, scrappy, and hungry" references.) The cookbook’s official release is on November 21—but until then, you can stave off your appetite for all things Hamilton-related by downloading the musical’s new app.

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fun
Never Buy Drawing Paper Again With This Endlessly Reusable Art Notebook
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Art supplies can get pricey when you’re letting your kid’s creativity run wild. But with an endlessly reusable notebook, you never have to worry about running out of paper during that after-school coloring session.

The creators of the erasable Rocketbook Wave have come out with a new version of their signature product meant especially for color drawings. The connected Rocketbook Color notebook allows you to send images drawn on its pages to Google Drive or other cloud services with your phone, then erase the pages by sticking the whole notebook in the microwave. You get a digital copy of your work (one that, with more vibrant colors, might look even better than the original) and get to go on drawing almost immediately after you fill the book.

An animated view of a notebook’s pages changing between different drawings.

There’s no special equipment involved beyond the notebook itself. The Rocketbook Color works with Crayola and other brands’ washable crayons and colored pencils, plus dry-erase markers. The pages are designed to be smudge-proof, so turning the page won’t ruin the art on the other side even if you are using dry-erase markers.

Rocketbook’s marketing is aimed at kids, but adults like to save paper, too. Break away from the adult coloring books and go free-form. If it doesn’t quite work out, you can just erase it forever.

The notebooks are $20 each on Kickstarter.

All images courtesy Rocketbook

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