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.

Friday’s Best Amazon Deals Include Digital Projectors, Ugly Christmas Sweaters, and Speakers

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10 Illuminating Facts About A Christmas Story's Leg Lamp

It's a Major Award!
It's a Major Award!
Tim Evanson, Flickr // CC BY-SA 2.0

When A Christmas Story was first released in 1983, it was a sleeper that attracted only a small (but quite cultish) following. Over the past three decades, however, the film has steadily become a holiday staple on par with classics like A Charlie Brown Christmas (1965) and Miracle on 34th Street (1947). And as the film itself has grown in popularity, so has one of its most recognizable props: the leg lamp, that glowing gam otherwise known as “A Major Award.”

1. The A Christmas Story leg lamp was inspired by an old-school soft drink.

Before A Christmas Story was a movie, it was a series of short stories that appeared in two different volumes by the late writer and radio personality Jean Shepherd. The books, In God We Trust: All Others Pay Cash and Wanda Hickey’s Night of Golden Memories and Other Disasters, were fictionalized accounts of Shepherd’s childhood in Depression-era Indiana (though the movie was filmed mostly in Cleveland, Ohio). Shepherd describes the leg lamp and his father’s obsession with it in a 1966 story titled “My Old Man and the Lascivious Special Award that Heralded the Birth of Pop Art.”

According to A Christmas Story House and Museum (yep, there’s an entire museum dedicated to the subject), Shepherd imagined the leg lamp after seeing an illuminated Nehi Soda advertisement, which featured two shapely disembodied legs up to the knee. Shepherd gave cloaked credit to Nehi by writing that the Old Man’s crossword contest was sponsored by an “orange pop” company whose name “was a play on words, involving the lady’s knee.”

When the lamp finally arrives in Shepherd’s essay, he writes, “From ankle to thigh the translucent flesh radiated a vibrant, sensual, luminous orange-yellow-pinkish nimbus of Pagan fire. All it needed was tom-toms and maybe a gong or two. And a tenor singing in a high, quavery, earnest voice: ‘A pretty girl/Is like a melody…’”

2. The A Christmas Story leg lamp was immortalized by production designer Reuben Freed.

Uncertain of just what a leg lamp should look like, A Christmas Story’s production designer Reuben Freed created a quick sketch and showed it to Shepherd, who surprisingly approved it right away. “I immediately thought of something I had seen in my mother’s front room, which was sort of a gold-colored silk lampshade, pleated with fringe around it,” Freed told Cleveland magazine in 2009. “I thought of it immediately and never thought of anything else—just that classic, big ugly shape.”

3. The “original” A Christmas Story leg lamp no longer exists.

Finding an original leg lamp is considered the ultimate feat for A Christmas Story aficionados, Caseen Gaines wrote in A Christmas Story: Behind the Scenes of a Holiday Classic. But “the likelihood of finding one is about as great as locating Pee Wee Herman’s bicycle in the basement of the Alamo.” Freed produced three leg lamps for the movie, but none of them survived the production. All three were broken during filming.

4. There’s a simple reason for the typo on the box the A Christmas Story leg lamp is delivered in.

When the leg lamp arrives at Ralphie’s house in the movie, it’s in a crate labeled not only with the infamous “FRAGILE,” but also “HIS END UP.” Though the use of “his” in place of “this” might seem like a subtle joke, the crate was indeed originally labeled “THIS END UP,” but no one had bothered to measure the container before trying to wheel it through the door. Jim Moralevitz, an actor who played one of the leg-lamp delivery guys, told Cleveland’s News-Herald, “I had the pleasure of delivering the major award 30 years ago. Unfortunately, the crate was so wide that it wouldn’t fit through the door. So they called in the carpenters and they took four inches off.”

5. The A Christmas Story leg lamp is big in Cleveland.

Erik Drost, Flickr // CC BY 2.0

Because much of A Christmas Story was filmed in Cleveland, the city has embraced the movie as its own (possibly to the resentment of Shepherd’s native Indiana). In 2013, to celebrate the movie’s 30th anniversary, Terminal Tower in Cleveland’s Public Square was turned into a giant leg lamp, complete with a red garter.

Terminal Tower can be seen, sans leg-lamp accoutrements, in A Christmas Story’s first few opening shots, looming over Higbee’s department store, where Ralphie first spots the coveted Red Ryder BB gun.

6. The A Christmas Story leg lamp is also a big deal in Long Island.

In 2005, the Reichert family, owners of the Northport Hardware Store in Northport, Long Island, got a goofy idea after attending the mayor’s Christmas tree lighting ceremony. They browsed through the store’s generous stock of leg lamps, called over some of the guys from the bar next door, and ceremoniously lit one of the lamps in the store’s picture window. Then they all cheered.

Somehow the Reicherts’s lighting of the leg lamp caught on and it has become an annual Northport tradition, though their store no longer hosts the festivities.

7. The A Christmas Story leg lamp is a hit on Halloween.

The leg lamp has become so popular, you can now purchase ready-made Halloween costumes in its likeness. In 2012, Josh Sundquist, a paralympian, motivational speaker, and author who lost his leg to cancer when he was 9 years old, won Halloween when he decided to make his own leg lamp costume. He even shaved his leg for authenticity.

8. The A Christmas Story leg lamp has been a star on the stage.

In 2012, A Christmas Story: The Musical opened on Broadway at the Lunt-Fontanne Theater. The leg lamp was celebrated with a kick line—only the Broadway chorus kicked up not only their own legs, but also fishnet-clad leg lamps.

The year before, at the Falcon Theatre in Burbank, California, the Troubadour Theater Company performed A Christmas Westside Story, a mashup of A Christmas Story and the epic tale of the Sharks and the Jets. What song did the leg lamp get to sing? None other than “I Feel Pretty.”

9. The A Christmas Story leg lamp is a hot commodity.

Steam Pipe Trunk Distribution Venue, Flickr // CC BY 2.0

According to a post-Christmas press release that highlighted Amazon’s seasonal sales in 2012, the online retail giant boasted: “If you stacked every Christmas Story Leg Lamp purchased by Amazon customers this holiday season, the height would reach the top of Mt. Everest.”

10. The A Christmas Story leg lamp gave rise to a hilarious catchphrase.

“Fra-gee-lay. It must be Italian!” has graced everything from baby onesies to novelty shirts to kitschy home decor.