Is it often that you share riddles with your family and friends? Do you have a huge collection of riddles and like showing them off at a party or get-together with your favorite people?
Do you like history? Do you want to increase your collection of riddles – this time with the most ancient of them all?
Well, I can help you with that!
Riddles are, no doubt, fun. They increase your vocabulary, brush your problem-solving abilities, make you better at socializing, and whatnot.
As a mommy, what I like the most about riddles is that they can keep your kids engaged – for a long time. And that is like a blessing for parents, if you know what I mean.
Riddles make you think. You are given some clues, and you must come up with a correct answer.
This whole thing makes you use your brain. You use not one but many ways to find the right answer. When you say a wrong answer, you try to think about it differently so that you can find the right solution to it.
This is a great exercise for your brain.
Now, if you are a fan of riddles, I know what ancient riddles will mean to you. And so, I have come up with the best of the m that are that have managed to pass the test of time.
The best part?
Some famous personalities said them!
Most Famous Ancient Riddles That Will Blow Your Mind
I like history. The thing of the past excites me. I like visiting old monuments, palaces, and places that have some history attached to them.
I get goosebumps in one of those places and hear about its history. And so, I go to such places again and again.
I had the same feeling when I heard about ancient riddles. Imagining that these riddles are told by some very older people in the past and are then carried forward to future generations gives me all the chills.
If you are anywhere like me, you will understand what feeling I’m talking about here.
So, there were some great riddlers among our ancestors too. Isn’t it?
I have made a collection of some of the oldest riddles in history. You can read them, memorize them, share them with your near ones, or just admire them – the choice is yours!
Don’t worry, thinking about what the answers to these old riddles could be. I have included the answers too. You can thank me later.
Are you excited?
1. The Most Ancient Riddle of the World
Did you know that four thousand years ago, people used to test each other’s critical thinking abilities with the help of riddles?
Well, yes. People were intelligent back then, too!
The riddle I’m talking about here is the oldest of all riddles – in the history of humankind. This is an ancient Sumerian riddle, and it has stood the test of time, I must say.
The land of Sumer was where the Sumerians lived. It is Iraq at present.
They wrote this riddle – an example of the earliest written riddle.
Did I tell you that apart from writing riddles, they created one of the most ancient writing systems as well?
So, do you think you can crack the oldest riddle below?
A house based on a foundation like the skies. A house one has covered with a veil like a secret box. A house set on a base like a goose. One enters it blind but leaves it seeing. What is it?A school
The Sumerians were very serious when it came to knowledge and education. As a result, they made some amazing mathematical discoveries tha t people still use today.
2. Sophocles: The Sphinx’s Riddle
Did I tell you how old this riddle this? How about I tell you it was written in the 5th century B.C.?
Well, yes. It is that old.
Did you read “Oedipus the King”?
It can be regarded as one of history’s most popular pieces of literature. So, no doubt, it gave us a much-loved riddle that I will share with you here.
Now, coming to the sad story of Oedipus, he gave the right answer to the riddle asked by the Sphinx.
He has a tragic destiny that he wants to avoid so much but cannot. However, he became very happy when he answered the Sphinx riddle correctly.
If you are not much aware of the story, let me tell you a bit of the synopsis.
The monstrous Sphinx has the body of a lion with the head of a woman. She was the guard of the gates in the city of Thebes.
The Sphinx would ask them a riddle whenever a traveler tried to enter through the gates. If they could answer it correctly, they could only enter the city.
But if someone got the answer wrong, the Sphinx would eat them up.
When Oedipus tried to enter Thebes, the Sphinx asked him a riddle, and he got the answer right.
Do you know what the riddle was?
What goes on four legs in the morning, two legs at noon, and three in the evening?A human
When a human is born as a baby, they crawl on their hands and knees. When they are in their mid-life, they walk on two legs.
And when they enter their old age, they use a cane or a stick to walk.
3. Samson’s Riddle in the Bible
Here comes another of the oldest riddles in the history of riddles. Well, it is not as old as the ancient Sumer one, but it sure is one of the oldest.
It was written back in the 6th or 8th century B.C., probably. So, now you know how it is one of the oldest ones.
Have you read the Book of Judges?
In the Old Testament, it comes at number seven.
In it, Samson asks a riddle to thirty people whom he invited to dinner. He tells them that if they succeed in giving the answer to the riddles correctly, they will get thirty pieces of clothing that are really expensive.
It was a rigged riddle. This means not everyone can guess it correctly, as it was something that only a handful of people who knew Samson closely would have the chance to know.
Okay, so now, you don’t have to scratch your head looking for the answer. I have included it here.
Q: Out of the eater, something to eat; out of the strong, something sweet. What am I?Bees making a honeycomb inside the carcass of a lion
Now, this is definitely a hard one, I must say.
Before that very feast, Samson had killed a lion without any weapon. And then found out that there were bees inside that lion’s body making a hive.
Here, the “strong” and “eater” in the riddle are the lion. The “sweet” and “something to eat” was the honey.
4. The Riddle of Venice by William Shakespeare
Are you a fan of Shakespeare? Have you read all that he has written? How about the Merchant of Venice?
If you are an avid reader of Shakespeare, you may not find this riddle to be much more difficult. But when he asked this riddle in his literature, it was a hard one for all his characters.
In the Merchant of Venice, Portia is the young heiress. Her father wants her to marry a worthy suitor, so he makes a puzzle.
He asked her suitors to select one of three caskets that he presented in front of them. There was one gold, one silver, and one lead casket.
Inside one of these three caskets, there was a picture of Portia. The one who can select the right casket will win his daughter Portia.
In order to choose the right casket, he presented the suitors with three clues. Read the following.
Gold casket: “Who chooseth me shall gain what many men desire.”
Silver casket: “Who chooseth me shall get as much as he deserves.”
Lead casket: “Who chooseth me must give and hazard all he hath.”The lead casket contains Portia’s picture.
One suitor chooses the gold casket and finds a skull with a note that says, “All that glisters (glitters) is not gold.” It warns him that if he continues to value things just by looking at their beauty, it will be a mistake.
The one who opens the silver casket finds the picture of a fool. He was a fool to think that he deserved to marry Portia. The note inside the casket says, “With one fool’s head I came to woo, / But I go away with two.”
The one who opens the lead casket gets to marry Portia. Her father understands that this man will work hard and make all the sacrifices that their marriage needs.
Also, it turns out that this is the man who Portia is in love with.
5. The Riddle of Emma: Jane Austen
I’m a big fan of Jane Austin. I have read all her novels, and Pride and Prejudice is my favorite.
Are you a fan of Jane Austen too? Have you read her 1815 novel, Emma?
If you have, you may already know the answer to the riddle I’m going to talk about here.
Emma, the main character in the novel “Emma,” solves the riddle of a mercenary suitor and outwits him.
Do you want to try to solve it?
Here it is:
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!
What am I?Courtship
You can think of this riddle in two parts. The first part of the riddle means the court, and the second part of the riddle represents the ship.
The man with the riddle was feeling confident for sure, as he thought that he could win Emma with his riddle. But nothing of that sort happened as Emma turned his proposal down.
6. An Eighteenth-Century England Vengeance Riddle
Did I tell you that this riddle started out as a nursery rhyme back in the seventeenth century?
People call it “As I was going to St. Ives.”
A fishing town in Cornwall is known as St. Ives. This riddle first appeared in a manuscript written in the year 1730. But it came to people’s attention in the threequel of Die Hard, named Die Hard with a Vengeance.
The villain in this movie asks Samuel L. Jackson and Bruce Wills to answer this riddle correctly in just thirty seconds. If they fail to do so, a bomb will go off on a city block that is full of people.
Here’s the riddle for you to crack:
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?One
In the movie, Samuel Johnson manages to find the right answer to the riddle at the last second.
This riddle is more like a trick question. It makes you think that you need to multiply multiple times. But the reality is just the opposite. All you need is to think wisely.
7. The Riddle of Alice in Wonderland
Have you read the classic novel Alice’s Adventure in Wonderland by Lewis Carroll?
It was the year 1865 when this novel got published. I loved it so much that I not only read the novel but also watched the movie multiple times when it was released.
There is so much happening in the novel, and you can’t ignore the riddles.
Here I have listed an old riddle that was asked by the Hatter at the Mad Tea Party to Alice.
Do you want to give it a try?
Why is a raven like a writing desk?The Mad Hatter hasn’t the slightest idea, and neither do we.
Do you know why this riddle became so famous?
Well, one reason is that there is no answer to it. Alice couldn’t find the answer and asked Hatter about the answer when he said, “I haven’t the slightest idea!”
So, this was basically a question. Did you know that even Carroll said that he hadn’t thought of an answer while writing this question?
But you know, when you write something, you need to be able to answer everything that is related to it.
So, after a lot of pestering from the readers, Carroll came up with the answer eventually.
He wrote in a preface to a newer edition of Wonderland, “because it can produce a few notes, though they are very flat; and it is never put with the wrong end in front!”
8. The Dilemma of a Wise Man
Here comes another of the most ancient riddles of them all.
Would you believe me if I told you that this riddle hails from 570 B.C.?
Yes. This old riddle is taken from one of Greece’s seven wise men. Do you think you can shed some light on it?
Come, see if you can!
Who is this father who has twice six sons? These sons have thirty daughters apiece, particolored, having one cheek white and the other black. They never see each other’s faces nor live more than twenty-four hours each.Twelve months
This riddle is all about time.
Here the sons in the first line represent the twelve months. There are thirty days in each month. The daughters here represent the days – half day and half night.
The days come with a duration of twenty hours each, and they never meet.
9. The Fatal Plight of Homer
There are so many ancient riddles out there that sorting them in terms of antiquity is quite a task.
This riddle is taken from the story of Homer. Have you heard of this famous Greek port?
Well, I suppose, you already have. Did you know that he went to the island of Los and got in touch with a handful of fishermen there?
When he wanted to know from them, “how is your day?” they gave him a reply with a riddle. It is that riddle that I’m going to talk about here.
So, people said that Homer failed to understand what the correct answer to that riddle could be. And so, he stayed on that island until his last breath.
Tell me, how good are you at solving riddles? Do you think you can solve this one that even Homer couldn’t?
Give it a try.
Q: What we caught, we threw away; what we didn’t catch, we kept. What did we keep?Lice
Lice are something that the fisherman kept. But as I said, Homer didn’t get the answer right.
The fishermen were very crafty, I must say!
10. Amazing Chinese Character Riddles
Do you know how to read or speak Chinese?
If not, then this ancient is going to be really tough for you even to understand the meaning of the lines.
This language is nowhere near the language of the Germans, Romans, or even Italians. Yet, it has a world of its own.
Chinese character riddles basically mean you have to determine the meaning of all the combined characters. Knowing just the meaning of a string of those characters will not do.
Here I have included one of the oldest Chinese character riddles.
If you read these characters literally, it will read as “yellow silk, young maiden, grandson, mortar.”
When Chinese characters are combined, you get a different meaning altogether.
The answer to this riddle means utterly wonderful, lovely words.
In order to get the answer, you have to combine the characters 色絲 first. This translates to color silk. And then when you do that separately, you get 絕. This holds the meaning of utterly.
Secondly, you have to combine the characters 少女 so that you get
妙 separately. When combined, it means young maiden. And then, when you separate it, it gets the meaning wonderful.
Thirdly, you have to combine the characters 女子 so that you get 好 separately. When combined, it means the son of a woman. And then, when you separate it, it gets the meaning of good or lovely.
Finally, you have to combine the characters 受辛 so that you get 辭 separately. When combined, it means words.
You need to put everything together to get the final answer.
Don’t worry if you don’t get the right answer to this old riddle. When it comes to Chinese character riddles, know that they are of a different kind than the regular ones.
So, if you want to answer them correctly, you may need to know the Chinese language first.
11. Persian Riddles
Do you know what the ancient Persians are famous for?
Well, they are well-known for their poetry, music, and art. But not only that, they are popular for their complicated riddles too.
The one that I have mentioned here is anonymous. People are not sure who the speaker was. But I can definitely say that it was written between the 9th and 11th centuries. You can find it in the Shams-i Qeys Kitāb al-mu’jam.
Here it goes.
What is it that tears into small pieces, whatever falls in its toothless mouth? If you put your fingers in its eyes, it will instantly prick up its ears.Scissors
This riddle seems simple when you hear its answer. But when you hear it for the first time, you start thinking about what a complicated thing it can be. Isn’t it?
12. The Riddle of Gollum
Are you aware of how many riddles were exchanged during the encounter between Gollum and Bilbo?
Well, there were five in number.
In the “Lord of the Rings” precursor that was written in 1937, we can see that the titular Hobbit named Bilbo Baggins, is solving riddles.
These riddles were given by Gollum, the evil and Bilbo was seen answering them as he wanted to escape from his underground lair.
Gollum can be seen telling Bilbo that he will allow him to pass safely only if the latter can give answers to all his questions correctly.
Here is the fifth one for you to solve. Of course, I have included the answer in case you can’t find a solution to it.
This thing all things devours;
Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays king, ruins town,
And beats mountain down.
What is it?Time
Well, Bilbo was successful in answering all the previous four riddles given by Gollum correctly. But he wanted more time to solve this riddle.
He spoke the word “time,” and Gollum thought he was answering the riddle. So, you can say Bilbo was lucky with this one.
13. A Fishy Riddle by Albert Einstein
Did you know that people say this riddle was created by none other than Albert Einstein?
It doesn’t fall under the category of literary riddles, but it sure is famous in history – all thanks to its supposed creator.
No such proof says the owner of this riddle is the famous Albert Einstein, but people say he did. Also, they say that this man predicted not many men would be able to answer it – only two percent – maybe.
Well, I think it would be great if Einstein had a bit more faith on us – his predecessors. Because, you know, it is not that hard. And if you try, you might be able to crack it too.
All you need is to guess the clues right by using proper logic. The following are the clues for you.
The Brit lives in the red house.
The Swede has a pet dog.
The Dane drinks tea.
The green house is directly to the left of the white house.
The person in the green house drinks coffee.
The person who smokes Pall Mall has a pet bird.
The person in the yellow house smokes Dunhill cigars.
The person in the center house drinks milk.
The Norwegian lives in the first house.
The person who smokes Blends lives next to the person with the pet cat.
The person with the pet horse lives next to the one who smokes Dunhill.
The person who smokes BlueMaster drinks beer.
The German smokes Prince.
The Norwegian lives next to the blue house.
The person who smokes Blends has a neighbor who drinks water.
Who among these persons owns the pet fish?The German owns the fish
There is a row in which there are five houses. Each house has a different color and a different person as a resident.
In addition, each person has a different nationality, smokes a different kind of cigar, drinks a different kind of beverage, and has a different pet animal.
And you needed to find the answer to this riddle depending on the fifteen clues mentioned already.
You can make a chart with each house and then fill them with all the information you have about them. This way it will be easier for you to find the answer.
14. The Riddles of Allfather
Odin made up multiple riddles in order to fool King Heidrek. I’ll talk about a few here.
Let’s start with the first one.
Did I tell you that this ancient riddle has its roots in the legends of Norse mythology?
People say that the riddle is created by Odin. He made this up so that he can fool King Heidrek.
Here it goes.
Four hang, four sprang, two point the way, two to ward off dogs, one dangles after, always rather dirty.
What am I?A cow
Isn’t this riddle an intelligent one?
The following is the second riddle created by Odin in order to challenge King Heidrek. Do you think you know the answer?
Mankind it mars, speech it hinders, yet speech it will inspire.”
What is it?Ale
The following is the third riddle that Odin made up so that he could save Gestumblini. And again, he presented this in front of King Heidrek.
It goes like this:
From home, I went. From home, I made my way. I saw a road of roads, and a road under them, and a road over them, and a road on all sides. What are we?Rivers
15. The Other Sphinx’s Riddle in Harry Potter and the Goblet of Fire
This riddle is not that old, but if I don’t include this in the list of riddles, then the list might seem incomplete.
So, tell me, are you a fan of Harry Potter? Have you read all his books? Have you watched all his movies?
Well, I have. I’m a big fan of Harry Potter. I have read and watched all the movies from the series – not once but multiple times!
In the fourth book of the Harry Potter series, you can see that a dangerous yet magical competition known as Triwizard Tournament is held, and Harry has to take part in it.
In order to complete the final task, he needs to go through a maze that is filled with many obstacles. Unfortunately, a Sphinx is one of those obstacles. She won’t allow Harry to pass until he answers her riddle correctly.
From this, you get to know how good J.K. Rowling’s knowledge of literary history is. Because, you know, Sphinx plays a very important role as a riddle-teller in the history of literature.
And J. K. Rowling chooses this magical creature to measure how good Harry is at cracking riddles.
Here goes the riddle.
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?A spider
There are three parts to this riddle.
In the first part, the spy is the liar who is in disguise. You have to solve all three parts in order to get the final answer right.
Harry solves all three parts of this riddle successfully and then gets the final correct answer which is “spy-d-er” or spider, after combining the three answers.
As a result, the Sphinx allowed him to go through. A few moments after that, he was actually face to face with a huge spider in that very maze.
This riddle acted as a warning to Harry, you can say.
16. The Lord of Mysteries
Have you read The Hobbit?
If your answer is “yes,” then I assume you already know how powerful the literary of J.R.R. Tolkien is!
He created some great novels, poetry, and fictional languages and was pretty good at making riddles.
Of course, this one is not that ancient, but it is still counted among the old and most famous riddles in the history.
This is one of the five riddles that Gollum asks Bilbo during their encounter in the Misty Mountains.
I mentioned another of Gollum’s riddles in a previous section, and here goes another one.
Thirty white horses on a red hill: first, they champ, then they stamp, then they stand still. What are they?Teeth
Don’t you find this riddle interesting?
17. A Complex Puzzle in Ulysses
Have you read the critically-praised all-time favorite in the history of literature, Ulysses?
Written by James Joyce, this is another timeless novel. The main character in this novel is Stephen Dedalus. He can be seen taking a class on Roman history, and that is when he asks his students this riddle in this novel.
People say that this character represents the author himself.
This is a complex riddle with such a complex answer that it left his students and his readers in doubt.
People started thinking that Joyce was actually making fun of riddles. Hence he came up with such as specific one. Some say that he is making fun of people who take riddles very seriously.
So, here it goes.
The cock crew,
The sky was blue:
The bells in heaven
Were striking eleven.
‘Tis time for this poor soul
To go to heaven
What is it?The fox burying his grandmother under a holly bush
Are you pulling your hair right now?
Well, that is what Joyce, maybe. In the “Notes for Joyce,” Don Gifford says that this riddle in Ulysses “is unanswerable unless the answer is already known.”
Did you enjoy these ancient riddles? Were they too hard for you to crack or you cracked them easily?
Well, if you ask me, some of these riddles went right above my head! I found them to be really tricky.
But you know, there is something about these oldest riddles that I liked so much, no matter how hard they were to solve.
Do you want me to add more to this list?
Let me know in the comments!
Hi, I am Claudia, I run TheQueenMomma’s content creation team, personally focusing on topics which add joy to people’s life. You would usually see me writing on topics like Jokes, Riddles, Truth & Dare as well as Baby Names etc.
In my professional career, I have a Bachelor’s and Master’s in sociology and specialize in media and crime. Once I finished my education, I began my career working as a journalist, reporting on various topics like crime, justice and family law. Even though I valued journalism, I came to the realization that I wanted to have a more immediate impact in people’s lives as well as bring joy to them.