Can you solve 11 of history’s most puzzling riddles? 

Riddles are among the oldest forms of entertainment; some date back thousands of years but are still maddening to unravel. See if you can solve all 11 of the most famous and beloved in history. (Answers at the bottom of the page.

Sphinx riddle


1. Riddle of the Sphinx

The Sphinx guarded the entrance to the Greek city of Thebes, demanding all travelers answer a riddle correctly before they could pass. The legendary question is quite possibly the most famous riddle in history: "Which creature has one voice and yet becomes four-footed, and two-footed, and three-footed?"

Or, in more modern language: “What goes on four legs in the morning, two legs at noon, and three in the evening?”

Greek island of Ios and Homer riddle


2. Homer’s riddle 

The poet Homer is said to have met fishermen while visiting the Greek island of Ios. According to legend, Homer asked about their day and the fishermen responded with a riddle.  


ANSWERS:

1. Oedipus solved the Sphinx's riddle: "Man - who crawls on all fours as a baby, then walks on two feet as an adult, and then uses a walking stick in old age."

2. Lice.

3. A school.

4. Teeth.

5.  The answer is honey from the lion's carcass. Honey is ‘something to eat’ and ‘something sweet’, and lion is ‘the eater’ and ‘something strong’.

6. According to Lewis Carroll: “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.”

Fans too have come up with plenty of their own solutions to the Hatter’s riddle.

7. The answer is courtship (wooing).

8. A cow.

9. The German owns the fish. (If you’re still stumped, here’s how one riddle solver came up with the solution.) 

10. A spider. This is a tricky riddle that needs to be broken down by individual parts, then strung together. The first two lines refer to a ‘spy’. With this hint, can you unscramble the rest? 

11. Bassanio proves himself worthy of Portia by ignoring the superficial glitter of the gold and silver caskets. The lead casket, symbolizing humility and modesty, is the correct choice: "Who chooseth me must give and hazard all he hath."

Can you solve 11 of history’s most puzzling riddles? 

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Riddles are among the oldest forms of entertainment; some date back thousands of years but are still maddening to unravel. See if you can solve all 11 of the most famous and beloved in history. (Answers at the bottom of the page.

Sphinx riddle


1. Riddle of the Sphinx

The Sphinx guarded the entrance to the Greek city of Thebes, demanding all travelers answer a riddle correctly before they could pass. The legendary question is quite possibly the most famous riddle in history: "Which creature has one voice and yet becomes four-footed, and two-footed, and three-footed?"

Or, in more modern language: “What goes on four legs in the morning, two legs at noon, and three in the evening?”

Greek island of Ios and Homer riddle


2. Homer’s riddle 

The poet Homer is said to have met fishermen while visiting the Greek island of Ios. According to legend, Homer asked about their day and the fishermen responded with a riddle.  

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Unable to answer, Homer remained on the island searching for the answer to this question until his death: “What we caught, we threw away; what we didn’t catch, we kept. What did we keep?” 

Riddles from the Middle East


3. Ancient Sumerian Riddle

Can you solve this ancient Sumerian challenge which traces its roots thousands of years back to the Middle East?: A house you enter blind, but come out of with sight.

 

4. Tolkien riddle

J.R.R. Tolkien didn’t just create fictional languages, he conjured up much loved riddles. Try your hand at this mind teaser. Bilbo is in a riddle competition with Gollum in The Hobbit (1937) and must answer correctly in order to escape: “Thirty white horses on a red hill: first they champ, then they stamp, then they stand still. What are they?”
 

Lion riddle of the ancient world


5. Biblical riddle

In the Hebrew Bible, Samson poses a question to the Philistines that has served as a riddle for the ages: 'Out of the eater, something to eat; out of the strong, something sweet.' 

The Philistines, who were stumped, are believed to have extorted the answer from Samson's wife, who persuaded Samson to tell her. We’ve given you a photographic hint as a head start.

Alice in Wonderland Hatter's Tea Party

6. The Mad Hatter’s raven riddle

“Why is a raven like a writing desk?” the Mad Hatter asks in Alice in Wonderland (1865). If you don’t know, you’re not alone. Even the Hatter didn’t have a solution to one of the most famous literary riddles in history. Lewis Carroll eventually tacked on his solution to a later preface, however.

 

Jane Austen's Emma starring Gwenyth Paltrow


7. Jane Austen’s Emma riddle

Jane Austen’s beloved Emma (1815) - played by Gwyneth Paltrow in the movie - was a matchmaker who enjoyed ‘charades’, otherwise known as word riddles. Can you unravel what Emma is referring to? 

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!

But, ah! united, what reverse we have!
Man's boasted power and freedom, all are flown;
Lord of the earth and sea, he bends a slave,
And woman, lovely woman, reigns alone.

 

Odin riddle

8. Royal riddle

Scandinavia Norse mythology offers many brilliant riddles, including those by the God Odin. According to the myth, King Heidrek threatened to imprison Gestumblindi should he be unable to think up a riddle to stump his majesty. The challenge resulted in this riddle: “Four hang, four sprang, two point the way, two to ward off dogs, one dangles after, always rather dirty. What am I?”

Einstein's Goldfish riddle

9. Albert Einstein’s pet fish

This riddle may not date back thousands of years but its fame comes from its celebrated creator. Albert Einstein, the theoretical physicist born in Germany in 1879, is believed to have come up with this fishy brain teaser.  

Q: There are five houses in a row. Each house is painted a different color and has a person of a different nationality living in it. Each person drinks a different beverage, smokes a different type of cigar, and owns a different animal as a pet. Using these 15 clues, which person owns the pet fish?

i) The Brit lives in the red house.
ii) The Swede has a pet dog.
ii) The Dane drinks tea.
iv) The green house is directly to the left of the white house.
v) The person in the green house drinks coffee.
vi) The person who smokes Pall Mall has a pet bird.
vii) The person in the yellow house smokes Dunhill cigars.
viii) The person in the center house drinks milk.
ix) The Norwegian lives in the first house.
x) The person who smokes Blends lives next to the person with the pet cat.
xi) The person with the pet horse lives next to the one who smokes Dunhill.
xii) The person who smokes BlueMaster drinks beer.
xiii) The German smokes Prince.
xiv) The Norwegian lives next to the blue house.
xv) The person who smokes Blends has a neighbor who drinks water.  

Hogwart's school in Harry Potter

10. Harry Potter’s riddle of fire

Harry Potter is faced with a Sphinx and a riddle while in the maze in the Goblet of Fire. Can you untangle this word puzzle and string together the answer?

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 men,
The middle of the middle and the 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?

 

The Merchant of Venice riddle

11. The last word to Shakespeare

The British Bard was a famous playwright and wit who enjoyed wordplay. In The Merchant of Venice, Portia’s father tests her suitors by posing a riddle. The men are invited to choose between one of three caskets - gold, silver, or lead - each with an inscription. Portia’s photo is inside only one of them. The suitor must display his intellectual skills to win her hand in marriage. Can you deduce which is the correct casket from the following descriptions?

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.”


ANSWERS:

1. Oedipus solved the Sphinx's riddle: "Man - who crawls on all fours as a baby, then walks on two feet as an adult, and then uses a walking stick in old age."

2. Lice.

3. A school.

4. Teeth.

5.  The answer is honey from the lion's carcass. Honey is ‘something to eat’ and ‘something sweet’, and lion is ‘the eater’ and ‘something strong’.

6. According to Lewis Carroll: “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.”

Fans too have come up with plenty of their own solutions to the Hatter’s riddle.

7. The answer is courtship (wooing).

8. A cow.

9. The German owns the fish. (If you’re still stumped, here’s how one riddle solver came up with the solution.) 

10. A spider. This is a tricky riddle that needs to be broken down by individual parts, then strung together. The first two lines refer to a ‘spy’. With this hint, can you unscramble the rest? 

11. Bassanio proves himself worthy of Portia by ignoring the superficial glitter of the gold and silver caskets. The lead casket, symbolizing humility and modesty, is the correct choice: "Who chooseth me must give and hazard all he hath."

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