9 of History’s Best Riddles
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,
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
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
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