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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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Fearless Man Slices 26 Watermelons on His Stomach in 60 Seconds, Setting New Record
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Ashrita Furman, a 63-year-old New Yorker who holds the world record for setting the most Guinness World Records, just achieved another one. This time, it was for the most watermelons sliced on top of his stomach in 60 seconds, Nerdist reports.

Furman came up with the idea for the record himself, and while he didn’t have any competition, Guinness stipulated that he had to slice at least 20 watermelons to be recognized. He managed to cut through 26 melons with his tool of choice, a katana, in less than a minute. (He walked away without a scratch.)

Check out this spectacle (and serious ab workout) for yourself:

“I’m really thrilled,” Furman told Reuters after pulling off the feat. “My first reaction is I’m relieved that I didn’t kill myself and the second is that I’m exhilarated because it is not only a skillful record, but also it’s something that I invented and now it’s out there and other people can challenge it.”

Furman, who has been called “Mr. Versatility,” currently holds more than 200 Guinness records. He set his very first record in 1979 after completing 27,000 jumping jacks, and he hasn’t slowed down since. In the past near-40 years he has set the record for—among other feats—the most knives caught in a minute (54); the greatest distance traveled while juggling on a pogo stick (4 miles, 30 feet); and most grapes caught in his mouth in one minute (86).

[h/t Nerdist]

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Courtesy of Shout! Factory
No Strings Attached: The Puppet Satire of D.C. Follies
Courtesy of Shout! Factory
Courtesy of Shout! Factory

At one corner of the bar, Jack Nicholson is seducing Margaret Thatcher. At another, Richard Nixon is reconsidering the sins of his presidency. Before the night is out, Sylvester Stallone, Oliver North, and Dan Rather will all make appearances, each sporting slightly exaggerated features and misshapen heads.

For two seasons between 1987 and 1989, a fictional Washington, D.C. bar was the setting for this unlikely assembly of political and entertainment figures cast in foam and orbiting around the show’s only regular human performer, actor Fred Willard. D.C. Follies might have been the most peculiar thing to come from the minds of famed television duo Sid and Marty Krofft, and when the hallucinogenic H.R. Pufnstuf is on their resume, that’s saying something.

A screen capture from the 'D.C. Follies' television series
Courtesy of Shout! Factory

The satirical, syndicated half-hour series might not have been paying licensing fees to the UK’s ITV network, but there’s a good argument for why they should have. In 1984, the channel began airing Spitting Image, a sharp, cutting take on world affairs created by Peter Fluck and Roger Law that used hypnotically repugnant puppets to represent political figures and members of the British royal family. The altered reality allowed for skewering, with jokes and actions that would have seemed too mean-spirited in live-action made permissible by the fact that they were embodied by living caricatures. In one sketch, then-Prime Minister Thatcher wondered why the poor didn’t just “eat their own bodies,” while newspaper employees at reputed tabloid outlets were depicted as literal pigs. At the height of its popularity, Spitting Image was viewed by 18 million viewers weekly.

Although other UK comedy exports like Monty Python's Flying Circus had found success with American audiences, Spitting Image was strikingly topical and resonated best with British audiences. A series of American-oriented specials for NBC that aired in 1986 and 1987 did well, but not well enough to commit to a series. At the same time, Sid and Marty Krofft—who had made their last name synonymous with Saturday morning kid TV culture in the 1970s—were working on a show that would emulate Fluck and Law’s approach. Thatcher would take a back seat to Oliver North, Dan Quayle, and other sometimes scandalous figures in then-contemporary U.S. politics. With Willard cast as the bartender, D.C. Follies got picked up in 90 markets for syndication beginning in September 1987.

The Kroffts had experience with parody puppets, having crafted Elvis Presley in felt as far back as the 1950s and mounting an elaborate live show, Les Poupées de Paris (The Dolls of Paris), that featured topless puppets. Not quite as appalling in appearance as the Spitting Image cast, the near-life-size foam stand-ins cost between $1500 and $3000 apiece. Political cartoonists like Bob Myers, who contributed to the New York Daily News, would offer a design that puppet makers could use as inspiration for a sculpt. People with easily identifiable features, like the drooping lip of Stallone or the shock of bright red hair sported by Jim Bakker's mistress Jessica Hahn, were ideal.

Unlike Fluck and Law, who typically targeted elected officials, the Kroffts had to be more cautious when it came to legal consequences. While political figures were largely powerless to complain or litigate over puppet counterparts, celebrities tended to exercise more caution over their likeness. D.C. Follies got away with using Woody Allen, Dolly Parton, and a host of others, but Frank Sinatra threatened to sue if he showed up cast in foam. The show eventually added a disclaimer at the end reminding viewers it was meant to be taken in jest.

There was also the challenge of remaining topical in a fast-moving news cycle. Unlike most scripted series, D.C. Follies was taped just three days prior to air to avoid time-worn jokes. Marty Krofft told the press that a puppet could be crafted in just 36 hours if needed, making it easier for them to comment on that week’s headlines.

D.C. Follies premiered the weekend of September 26 and 27, 1987, an auspicious debut for a syndicated offering: It was the same weekend Star Trek: The Next Generation began airing. Often on late at night and sometimes opposite Saturday Night Live, Follies invited a number of human guest stars—Martin Mull was the first—who tried not to be upstaged by the vaguely disfigured effigies surrounding them. Marty Krofft allegedly recruited some guests simply by threatening to make a mocking puppet of them if they didn’t agree to appear.

A screen capture from the 'D.C. Follies' television series
Courtesy of Shout! Factory

Each week, Willard—who was apparently hired for his ability to make conversing with puppets seem plausible—lent a sympathetic ear to the problems expressed by his satirical patrons. The blend of characters and real guests made for some odd pairings: The real Mike Tyson once appeared to box a puppet George Bush. Freddy Krueger (Robert Englund in his familiar makeup) saddled up to the bar to help plug a new Nightmare on Elm Street movie. Krueger's nightmare: Quayle becoming president.

Mostly, though, the puppets walked in and out of frame in non-sequitur sketches. John Madden might accost Pope John Paul II; Jimmy Carter, Richard Nixon, and Gerald Ford were seen playing Trivial Pursuit, with Nixon admitting his Presidential Library was a Bookmobile; Madonna, Sean Penn, Jesse Jackson, Ted Koppel, and dozens of others also passed through.

Follies earned a second season while still filming its first, but ratings were never strong enough to warrant a third. (Late last year, Shout! Factory released the full series on DVD.) The Kroffts went on to produce similar puppet productions like Red Eye Express and Krofft Late Night. Nothing, however, seemed to endure quite like Spitting Image, which ran for 12 years in the UK and is currently being considered for a U.S.-based revival. Based on today’s political climate, there should be no shortage of material.

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