What makes a great riddle?

[Image courtesy of PNG Find.]

I have always suspected that riddles were our first experiments with puzzles and puzzly thinking. Long before crosswords, Sudoku, codebreaking, and magic squares, the potential for wordplay and outside-the-box thinking would have appealed to storytellers, teachers, philosophers, and other deep thinkers.

Who doesn’t enjoy unraveling a riddle, parsing the carefully constructed sentences for every hint and nuance lurking within, and then extracting that tiny purest nugget of a solution from the ether?

Riddles appeal to our love of story and adventure, of heroes with wits as sharp as their swords. Riddles are the domain of gatekeepers and tricksters, monsters and trap rooms from the best Dungeons & Dragons quests.

And so, for centuries upon centuries, even up to the modern day, riddles have been a challenging and intriguing part of the world of puzzling.

We can trace them back to the Greeks, to Ancient Sumeria, to the Bible through Samson, and to mythology through the Sphinx. Riddles abound in literature; we find riddles in Shakespeare, in the works of Joyce, Carroll, and Austen, all the way up to the modern day with The Hobbit and Harry Potter. Every locked room mystery and impossible crime is a riddle to be unraveled.

[Image courtesy of Campbell County Public Library.]

But this raises a crucial question: what makes a good riddle?

At first glance, it should be confusing or elusive. But after some thought, there should be enough information within the riddle to provide a solution, either through wordplay/punnery OR through looking at the problem from a different perspective.

Let’s look at an example. In this instance, we’ll examine the riddle from Jane Austen’s Emma, which is posed to the title character by a potential suitor:

My first displays the wealth and pomp of kings,
Lords of the earth! their luxury and ease.
Another view of man, my second brings,
Behold him there, the monarch of the seas!

The answer is “courtship.”

The first half of the riddle refers to the playground of royalty — court — and the second half to the domain of her suitor — ship — and when combined they form the suitor’s desire. This riddle is confusingly worded, to be sure, but it makes sense when analyzed and it’s totally reasonable when the clever Emma figures out the answer… and turns down the suitor’s attempt at riddly courtship.

[Image courtesy of Yale.edu.]

So, what’s an example of a bad riddle? Well, unfortunately, we don’t have to look too hard for an example of one. Let’s examine Samson’s riddle from The Book of Judges in the Old Testament, which he poses to his dinner guests (with a wager attached):

Out of the eater,
something to eat;
out of the strong,
something sweet.

The answer, bafflingly, is “bees making a honeycomb inside the carcass of a lion.”

This is borderline nonsense unless Samson actually told you the story of killing a lion with his bare hands and later returning to the corpse to find bees building a hive inside. So, basically, this riddle not only screws over his dinner guests — who lost a wager to buy fine clothing if they couldn’t solve the rigged riddle — and serves as an excuse to brag about killing a lion. Samson is a jerk.

This is a bad riddle, because it’s designed to be confusing, but does not offer enough information to get to the desired solution. It’s purposely unsolvable, and that sucks. Riddles shouldn’t be arbitrary or nonsensical.

James Joyce pulled this in Ulysses. Lewis Carroll pulled it in Alice’s Adventures in Wonderland. And each of these examples give riddles a bad name. (Even if they do serve a literary purpose, as scholars claim they do in the Joyce and Carroll examples.)

Even if you want the hero to seem (or be) smarter than the reader, the riddle should still make sense. When confronted with five riddles by Gollum in The Hobbit, Bilbo Baggins solves four of them (and answers the fifth through charmingly dumb luck). It doesn’t hurt his character or make the reader feel like they’re being cheated when these riddles are resolved.

That’s another quality of a great riddle. Even if you don’t solve it, when you DO find the answer, it should feel like you were outwitted and you learned something, not that you were involved in a rigged game.

Oh, and speaking of learning, that reminds me of another example of a challenging yet fair riddle, one that comes from Ancient Sumeria (now, modern-day Iraq):

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

The answer, as you might have puzzled out, is “a school.”

Riddles can be devious or tricky; they can rely on misdirection, our own assumptions and biases, or careful word choice to befuddle the reader. But they should always be learning experiences, like the house you enter blind and leave seeing.

What are some of your favorite riddles, fellow puzzlers? Let us know in the comments section below. We’d love to hear from you!

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Riddles, Riddles Everywhere!

I’ve had riddles on the brain recently, because I keep seeing them everywhere. Over the last few weeks, they’ve popped up in games, TV shows, books, and even emails to the blog.

It all started with our twice-monthly office D&D game. Every other Thursday, a group of us commandeers one of the conference rooms at lunchtime and enjoys an hour of dice-fueled storytelling, adventure, and fun.

As is often the case with a fantasy-inspired game, there was a river to cross and a riddle to answer in order to pass.

A murderer is condemned to death. He has to choose between three rooms. The first is full of raging fires, the second is full of assassins with loaded guns, and the third is full of lions that haven’t eaten in a year. Which room is safest for him?

This is a classic riddle, usually titled “Three Doors” or “The Murderer’s Riddle.”


And when you’ve got a team of puzzle solvers in your D&D group, this riddle is no challenge at all.

(If you’re curious about the solution, you pick door #3. After a year of not eating, the lions would be dead, so it would be safe to enter that room.)

Later on in the game, we again had to barter passage across a body of water, either answering a riddle or battling a demon to the death.

Naturally, we chose the riddle.

What is the creature that walks on four legs in the morning, two legs at noon and three in the evening?

This is another classic riddle — the Riddle of the Sphinx, most famously solved by Oedipus — and posed no challenge to our merry band of misfit adventurers.

(If you don’t know this one, the answer is “man,” since you walk on four legs as a child, aka crawling, two legs as an adult, and with a cane when you’re older. The day — morning, noon, and evening — represents a lifetime.)

We crossed the lake, and our adventure continued, and I thought I was done with riddles for a bit.

Then a few days later, I got caught up on the latest season of MTV’s The Challenge, a reality/competition game show. (I’ve written about some of their puzzly challenges in the past.)

And, wouldn’t you know it, this week’s challenge involved a riddle.


Both teams would start on this platform, sending pairs of swimmers out on a long swim to retrieve keys. Those four keys would then open both a chest full of letter tiles and a riddle to be solved. The first team to solve the riddle with the letters available would win the challenge.

Once all the drama of selecting partners — given that many of the players weren’t strong swimmers, and the slowest-swimming team would be eliminated from the game — there was plenty of tension to be had.

But finally, all four keys were retrieved by the teams, and the riddle revealed:


I am a 5 letter word.

I am normally below you.

If you remove my 1st letter, you’ll find me above you.

If you remove my 1st and 2nd letters, you can’t see me.

The teams were initially baffled, playing around with different words and various combinations of letter tiles in the hopes that it would spark something.


Eventually, competitor Ashley came up with a three-letter word that you couldn’t see — AIR — and her team quickly came up with the correct answer: CHAIR.

(A chair is normally below you, hair is above you (sorta), and air can’t be seen.)

So, three riddles in a matter of days. It’s officially a pattern. And so far, I’m three for three on solving these riddles.

A week or so later, though, yet another riddle arrived, this time by email. And I admit, I’m a little stumped.

What has a bell but isn’t a church. Is full of air but is not a balloon?

What do you think, fellow puzzlers and PuzzleNationers? Any ideas? Let me know in the comments section below. I have a few theories, but nothing that feels like a conclusive answer.

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Riddle me this!

The spirit of puzzle-solving has always been with us — every problem is a puzzle of some sort, after all — so it’s surprising to realize how relatively brief the history of paper puzzles is in the long run.

I mean, the Sudoku puzzle as we know it first appeared in print in Dell Magazines in 1979, a little over thirty years ago! (Yes, some puzzles with similar attributes appeared in French publications nearly a century before, but the Sudoku as we know it is a modern creation.)

This year marks the one-hundredth anniversary of the crossword puzzle. One hundred years! Amazing when you think about it, but also just a drop in the bucket when compared with the span of human history.

So, if the two most famous puzzles are both fairly recent developments, what sort of puzzles kept humans occupied for centuries and centuries before that?


Yes, plenty of wordplay and mathematical games predate the modern puzzles we know and love, like the famous ancient word square found in the ruins of Pompeii that features a Latin palindrome.

But I suspect that riddles were, in fact, our first experiments with puzzles and puzzly thinking.

They appeal to our love of story and adventure, of heroes with wits as sharp as their swords. Riddles are the domain of gatekeepers and tricksters, monsters and trap rooms from the best Dungeons & Dragons quests.

The Riddle of the Sphinx — in its most famous version: “What goes on four legs in the morning, on two legs at noon, and on three legs in the evening?” — has origins as far back as the story of Oedipus and the tales of Sophocles and Hesiod, more than 2000 years ago.

And variations of logic puzzles and riddles have been with us at least as long. Consider the famous “a cabbage, goat, and wolf” river crossing, or the Man with Seven Wives on the road to St. Ives.

Nearly one hundred and fifty years ago, Lewis Carroll unleashed a doozy of a riddle in Alice’s Adventures in Wonderland, one we discussed in detail in a recent blog post.

In more recent times, one of Batman’s most capable and dogged adversaries has employed riddles to confound and challenge the Caped Crusader.

His debut episode of Batman: The Animated Series features a corker of a riddle: “I have millions of eyes, yet I live in darkness. I have millions of ears, yet only four lobes. I have no muscles, yet I rule two hemispheres. What am I?”

While we’ll probably never be able to trace the history of riddles as definitively as that of crosswords and sudoku, it’s fascinating to consider just how long puzzles in one form or another have been with us.

And so, in the spirit of puzzling, here are a few riddles for the road. Enjoy.

A man lay dead on the floor, fifty-three bicycles on his back. What happened?

Bob walked into a bar and asked for a glass of water. The bartender pulled out a gun and pointed it at Bob’s face. A few seconds later, Bob said, “Thank you” and walked out. What happened?

Rhonda lay facedown in the middle of the desert. On her back was something that could have saved her life. What is it?

Frank did not want to go home because of what the masked man held in his hand. What is the masked man holding?

Joe was dead. Across his back was an iron bar. In front of him was some food. What happened?

[Answers will be posted on Friday!]

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