Solving Riddles

Praps ye sits here and chats with it a bitsy, my preciousss. It likes riddles, praps it does, does it?”

—Gollum, from JRR Tolkien’s The Hobbit

Hobbits are very skilled at riddles—much more so than, say, men or dwarves (or even elves). Being close to the earth, they understand its humor, and riddles are born of the earth.

Mr. Baggins, a pretty average hobbit (perhaps a little smarter and a little more courageous than most, though he doesn’t yet know it), is ready to take on the mysterious Gollum at riddling games. In fact, he even dares to think that he might beat the slimy creature. After all, hobbits spend a great deal of time sitting by the fire in the winter months making up and guessing at riddles. They’ve even come up with some questions that are remarkably difficult for other inhabitants of Middle-earth to guess.

If you’re confronted by riddles, here are some hints about how to approach them.

• RIDDLES ARE ALL ABOUT MISDIRECTION. The solutions are always obvious and standing in plain sight.
• RIDDLES ARE ABOUT WORD PLAY. Hobbits are fascinated by words—this is a sign of their connection to elves. The more you enjoy riddles and word games, the more elvish you are.
• RIDDLES ARE ANCIENT. Bilbo himself knows that even a very old creature such as Gollum is going to know the basic rules of riddling.
• RIDDLES ARE A KEY TO GREATER TRUTH. In fact, the adventures of Bilbo, and later of Frodo, are a great riddle, and one to which the answer ultimately lies in the Undying West.

Who Likes Riddles?

It’s quite possible you may come into situations in which riddles are the most reasonable response to a given challenge. If so, you might ask what kind of people (or creatures) are riddling you. Their reaction to riddles will probably reveal something about their personalities, too.

Elves and Riddles

Elves, on the whole, like riddles. Which is to say, they like random, nonresponsive, confusing answers to questions. Frodo comments to Gildor, “It is said, Go not to the Elves for counsel, for they will say both no and yes.” The elf admits the justice of this remark. Elrond also has a habit of making cryptic comments that don’t make much sense—unless you’re a half-elf or a wizard. And Galadriel is positively Delphic in most of her utterances while the Fellowship is vacationing in Lothlórien. All in all, the elves like a style of communication that is confusing, cryptic, and only understandable by other elves. This makes them highly susceptible to riddles and other guessing games.

The only problem with starting a riddling contest with an elf is that it’s likely to go on for days, as the riddles get more and more obscure, bound up in lore that’s thousands of years old and remembered only by the elves, and even then not many of them. So don’t start riddling with elves unless you have plenty of time on your hands and nothing urgent in the offing (such as saving Middle-earth from the Dark Lord by dropping his ring in a volcano).

Dwarves and Riddles

Dwarves are plain, down-to-Middle-earth folk with no time for nonsense—riddling or anything else. Dwarf lore is largely a matter of transmitting plain, ordinary fact, although every now and then there’s a bit of mysticism wrapped up in it, such as the Mirrormere and the myths surrounding Khazad-dûm. But who wants to spend his time speculating on the answers to obscure questions when there’s ale to be drunk, beards to be grown, and orcs to be slain?

If you want to start a riddling contest with a dwarf, be sure to make the stakes worth his while: a pile of gold coins, perhaps, or a trinket or two made of mithril; possibly a couple of barrels of well-brewed ale to go along with a nice stash of Longbottom Leaf (since dwarves are notorious connoisseurs of pipeweed).

Men and Riddles

Let’s face it: Compared to most other races of Middle-earth, men are a bit simpleminded. (The exception is Númenóreans, but there aren’t many of them around. We’re talking about normal, average, everyday men.) They aren’t nearly as mystic and complex as the elves, and they don’t have strong connections to the earth like dwarves do. However, they generally like riddling speech, as witness the strange dream that Faramir and then, once, Boromir have:

And so on.

In point of fact, men rather like riddles, since riddles are mysterious and allow for days—months, sometimes—of endless debate, thus shutting off any need to take action.

From this point of view, the best time to start a riddling contest with a man is when he’s contemplating some disastrous course of action and you want to delay him as long as possible from making an ass of himself and possibly bringing ruin on everyone else. Gods sometimes come down from the heavens to challenge mortal men to riddling contests as a way of testing man’s wisdom and deciding if they’re truly worthy of ruling.

Orcs and Riddles

Orcs don’t like riddles. They don’t like anything confusing. All they want is to get a plain answer to plain questions, preferably with a little torture to go with it, and then get on with slaughtering and rampaging. If you’re stuck in a dungeon with a couple of grumpy orcs, don’t try to riddle them. Spend your mental energy thinking of a way to escape with most of your skin intact.

Dragons and Riddles

Dragons like riddles. They’re fascinated by riddling speech, as witness Smaug’s reaction when Bilbo tells riddles during their conversation. There’s a lot of riddling talk, and Smaug loves it—which is why he doesn’t end the conversation right then and there by blowing Bilbo to ashes with his fiery breath. The rules here, if you’re talking to dragons, are:

• KEEP THE TOPICS LIGHT. Don’t spend any time on famous elvish warriors who’ve slain dragons or notable dwarves who’ve been able to defeat the great Wyrms of the North. Instead, stay on topics such as the weather, food, and what the well-dressed dragon is wearing this season.
• REMEMBER THAT DRAGONS ARE SENSITIVE TO THE SUBJECT OF WEALTH (ESPECIALLY THEIR OWN). Dragons have spent a good deal of time accumulating their hoards, so it’s very rude to suggest that anyone else might have a claim to them.
• GIVE THE DRAGON AN OPPORTUNITY TO SHOW OFF ITS JEWEL-ENCRUSTED UNDERBELLY BY TELLING IT HOW MAGNIFICENT IT IS. Dragons like to boast as much as the next magical beast. They also appreciate fulsome praise. Who knows? You may discover something useful.
• TRY NOT TO BRING UP PAST HEROES WHO MAY HAVE CHALLENGED THEM AND WHOSE DESCENDANTS ARE STILL AROUND, POSING A DISTANT, BUT NONETHELESS DISTINCT THREAT. Dragons, like other magical beasts, have extremely long memories.
• DON’T SHOPLIFT HIS TREASURE. For goodness sakes, this is just plain manners! How’d you like it if someone came into your house and stole the teaspoons? Just because a big two-handled goblet is lying there in plain sight is no reason to take it.

Hobbits

Hobbits love riddles and have a rich store of them. Except for one or two instances, Bilbo really isn’t at a loss for a riddle when Gollum presses him—except for the very end of the game when he rather unfairly demands to know, “What have I got in my pockets?” Experts and authorities have quite reasonably pointed out that this isn’t a riddle and therefore, by the strict rules of the game, Bilbo has lost. However, when he accepts the challenge to guess the answer to the hobbit’s question, Gollum implicitly also accepts the new rules and obligates himself to abide by the result. Of course he’s not going to. It’s just that from a strictly moral standpoint, he ought to.

If you challenge a hobbit to a riddle game, and the hobbit is stuck for a riddle (by which right, he ought to surrender the game), don’t give in if he starts asking irrelevant questions like “What have I got in my pockets?” or “What was the first name of my aunt’s mother’s grandmother’s second cousin?” If he can’t think of a true riddle, inform the hobbit that he’s lost; it’s as simple as that.

What Makes a Good Riddle?

Some riddles are based on word play; others are about what you don’t know. Bilbo is skilled at both. Others prove themselves somewhat less adept. Tolkien’s stories are filled with riddles, and it would make things easier for many of the characters if they could answer them earlier and more correctly.

Boromir’s Riddle

When he comes to the Council of Elrond, Boromir of Gondor tells the assembled elves, dwarves, hobbits, and men of a riddle that his brother, Faramir, heard in a dream:

On the surface, this is pretty clear, especially when it’s all explained to Boromir at the council. Yet he persists in misunderstanding bits of it, even when Tolkien practically hits him over the head with it. The same thing is true of Faramir when, later in the story, he actually meets Frodo and Samwise and learns of the Ring. We can only see Boromir’s failure to understand his riddle as a sign of the degeneration of the races of men and the evil that gnaws at the heart of Gondor. The lesson: When a bunch of elves, dwarves, hobbits, and men tell you something’s true—believe it.

Aragorn’s Riddle

When Bilbo first meets Aragon and the Ranger tells him his story, the hobbit is kind enough to make up a poem for the future king of Gondor in the form of riddling verse:

You can’t help feel that this is yet another example of hobbits and elves making things more difficult than they need to. If everyone knows Aragorn is the rightful king of Gondor, why not just say so? Surely it would make his claim to the throne stronger and make it harder for people such as Denethor to dispute the claim. Well, that’s elves and hobbits for you. Always mixing things up in riddle-speak.

The Riddle of the Dead

At a key moment in the War of the Ring, Aragorn and the Grey Company make a fateful decision: They will ride to the Stone of Erech and pass through the kingdom of the dead. At this point, the sons of Elrond bring a message from their father: “Bid Aragorn remember the words of the seer, and remember the paths of the dead.”

Not terribly encouraging words, on the whole, but the Ranger remembers (because he’s wise in the lore of Middle-earth) the words spoken by Malbeth the Seer:

“Dark ways, doubtless,” Gimli the dwarf remarks sourly, “but not darker than these staves are to me.” We can sympathize with the dwarf. After all, remember, dwarves like plain speech better than riddling talk, and these comments of the Seer are confusing at best. However, Aragorn, true heir of kings, understands them and takes them as an indication that at this dark hour he should ride the paths of the dead.

The lesson here is when you don’t have any better road, follow the riddle. Because, awful as its advice may be, it’s probably better than the alternative.

Riddles in the Dark

The most famous riddling contest in history is unquestionably when Bilbo meets Gollum deep in the bowels of the Misty Mountains. Neither is entirely sure of the other; each has something to gain from the other. And Bilbo has little choice but to play the game out to the end. We can all learn something from his selection of riddles.

What Has Roots as Nobody Sees

Gollum’s first riddle describes something

A logical choice, since that’s where he lives. What’s more surprising is that Bilbo gets it right so quickly. “Easy, ” he says. “Mountain, I suppose.” In fact, there’s nothing easy about it, since Bilbo comes from the gently rolling lands of the Shire, has never seen a mountain, and mistakes his first sight of the Misty Mountains for the Lonely Mountain, home of Smaug.

Thirty White Horses

Next Bilbo presents Gollum with his first riddle:

Well, if Gollum (as he tells Bilbo) “only has six,” how does he know this chestnut’s answer is “teeth”? Perhaps he’s heard of other creatures who have more teeth than he does. Good advice for us, to be aware that riddles are meant to stir our minds and make us think outside our usual confines.

Wind and Sun

The next two riddles in the contest are about elemental forces, neither of which is especially liked by the contestant at whom it’s directed. Gollum asks Bilbo about something that

And it takes Bilbo a few minutes to think of the answer: “Wind. Wind, of course.” He answers with a riddle that calls up images Gollum finds distasteful—making the point that if you’re ever stuck in a tight place, find something that your opponent likes much worse.

An Eye in a Blue Face

Gollum is used to living underground, so Bilbo naturally thinks something along these lines will fool him:

The answer—sun on daisies—upsets Gollum not so much for what it is than for the memories it evokes. It recalls distant days by the River when he used to go fishing with his cousin, Deagol. And, naturally, it causes him to make a mistake with his next riddle:

Well, the answer’s obvious, isn’t it? Dark.

Fish and Eggs

There’s nothing so obvious as that which you see every day. Bilbo thinks his riddle is dreadfully easy:

However, it puzzles Gollum for a good long time. He finally hisses the answer: eggs. The creature’s reply is equally simple:

But the hobbit is stumped, and he frantically turns over in his mind all the awful creatures who could be “cold as death.” At the last second the answer—fish—comes to him. The lesson: It’s the obvious things that are the most difficult.

Time, Time, Time

What could be more puzzling than something that conquers everything. Gollum asks,

Of course, there’s only one answer: Time. So when you’re out of luck and out of everything else—you’re never out of time.

What Has Bilbo Got in His Pocketses?

At the beginning of The Lord of the Rings, the author (in this case, presumably Frodo) observes, “The Authorities, it is true differ whether this last question [What have I got in my pockets] was a mere ‘question’ and not a ‘riddle’ according to the strict rule of the Game,” but everyone agrees that Gollum, having agreed to the rules, was bound to answer. The biggest question, of course, was who the “authorities” were. After all, who really decides what’s a riddle and what isn’t? It turns out that riddling has some pretty specific rules.

If You’re Going to Riddle, Know the Answers

Both Bilbo and Gollum know the answers to all the riddles they ask. That’s better than the folks of Gondor, for example. Aragorn recites the words of Malbeth the Seer:

He really has no idea what it means. Still, he knows, the best thing a king can do sometimes is to ride forward without question. So if you encounter a riddle to which you don’t know the answer, trust in fate and ride forward blindly. Maybe things will work out all right after all.

The Answer to a Riddle Should Make Sense

Doubtless you’ve listened to riddles, puzzled over them, and when the answer was given, thought, Well, of course! Why didn’t I think of that?

Some people, though, when riddling, keep the answers obscure or provide the answers in another language—Norwegian, or something.

This goes beyond cheating; it’s just irritating, and if you do this sort of thing to a dragon or a goblin, it’ll probably be the last riddle you tell.

Riddles Should Come at Appropriate Times, Or, Never Laugh at Live Dragons

Asking riddles when you’re cold, lost, and sitting on the edge of a dark lake, far underground, next to a slimy creature who has expressed a desire to eat you may not seem like the best time for a guessing game, but at least such a game would gain you some time to come up with a plan. The same is true when talking to a dragon. Dragons are fascinated by riddling talk, and you can keep them guessing as long as you keep your whereabouts concealed. However, when running down a narrow tunnel with an annoyed fire-breathing dragon behind you, it’s not the best time to throw riddles, insults, or anything else. Just concentrate on running fast. Really, really fast.

Short Riddles Are Usually Harder to Solve Than Long Ones

It’s notable that both Bilbo and Gollum ask short questions (in Bilbo’s case, the egg riddle, and for Gollum the fish riddle) that turn out to be dreadfully hard to figure out. That’s because short riddles give the guesser less to work with and more scope for confusion. Also remember that what’s obvious to you is usually not so clear for someone else. So the clue in constructing a successful riddle may lie in focusing on your everyday experiences rather than the strange or exotic.

Other Famous Riddles

If you’re stuck for a riddle, you might consider borrowing from riddles made famous by other great figures of history and legend. One of these is King Oedipus (better known, of course, for killing his father, marrying his mother, and giving us the Oedipus complex). As a young man, Oedipus confronted the Sphinx, the monster with the body of a lion and the head of a beautiful maiden. The Sphinx was accustomed to ask travelers a riddle; those who couldn’t answer correctly (which up to that point, had been everybody) she killed and devoured. In its traditional form, the riddle of the Sphinx goes:

The answer, of course, is man, who crawls when a baby, walks on two legs in the prime of his life, and when he’s old has to make use of a stick. Oedipus guessed the answer correctly, whereupon the Sphinx, taking defeat very hard, killed itself, and Oedipus became king of Thebes.

Alternate Versions

Another version of the Riddle of the Sphinx (and one that pays a greater tribute to Oedipus’s ingenuity in coming up with the correct answer) runs like this:

The answer is a man sits on a stool, his stick on his lap. A dog comes in and steals the stick, whereupon the man grabs the stool and throws it at the dog, forcing the animal to return the stick.

Still another version of the Sphinx’s riddle is:

Heidrek the Wise

In the Norse saga of King Heidrek the Wise, the god Odin, disguised as usual, shows up at Heidrek’s court to challenge the king to a riddling contest. Finally Odin asks:

Heidrek, living up to his name, answers that “The raven lives ever on the high fells, the dew falls ever in the deep dells, the fish lives without breath, and the rushing waterfall is never silent.” After this bit of wordplay, Odin has to concede that Heidrek is, indeed, wise.