10 Most Difficult Riddles the World Over. Some Are So Funny They Are Set to Tickle Your Funny Bone


From the olden times a storyteller’s tale runs a winding path and yet is sprinkled with humor, idioms, irony and sometimes can begin or stop at the middle with a riddle. Riddles are popular among children since their orientation to words and objects or events are catapulted by the imagination. This comprehension and habit forming exercise can stretch your mental capacities or simply tickle your funny bone. Here are some of the top ten most difficult riddles that you may be able to play a game with young and old alike.

A Politician’s Mind Game 

A Politician’s Mind Game

Riddles garner thinking out of the box and pose limitless idiosyncrasies just like the field of politics. Here is one that is rumored to be the favorite of Teddy Roosevelt. 

“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.”

The answer is, an actor.

Coming from the Ancient Sumerians

Coming from the Ancient Sumerians

Known for posing logic into problems riddles grant entertainment and exercise deeper comprehension and cause of debate. This one proves to be so.

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

The answer is, a school.

Riddles in Africa as a rite of passage

Riddles in Africa as a rite of passage

As oral tradition is treasured, culture cans sometimes dictate how riddles are used and what they are about.  There are elegant ways to put meanings into words and are effectively so in this case. Here are a few African riddles that are simple, playful yet conceal the answer too well.

From Ghana:

“What do you look at with one eye, but never with two?

Answer: The inside of a bottle.

Swahili of East Africa Riddle:

What things always chase each other but never overtake one another?

Answer: The wheels of a vehicle.

A West African Riddle:

Why is a man like pepper?”

Answer: Until you have tested him, you can’t tell how strong he is.

In Ancient Greece

In Ancient GreeceThe story behind this riddle states that the Greek poet Homer had met some fishermen on an island. Having greeted and asked how their day was the fishermen posed this riddle. Homer was never able to solve it and had stayed on the island until his death.

The Riddle is:

“What we caught, we threw away. We kept what we didn’t catch. What was it that we kept?”

The answer would be lice.

Some riddles identify with Biblical characters and quoted in a Bible text

Some riddles identify with Biblical characters and quoted in a Bible text

The hero and anti-hero is Samson who had superhuman strength. In a feast that he was hosting he wagered if anyone could solve this riddle.

Riddle: “Out of the eater, something to eat; out of the strong, something sweet.”  (Judges 14:14)

Answer: Bees that were making a honeycomb inside a lion’s carcass. Samson had killed the lion.

Tolkien’s inspiration

Tolkien’s inspiration

As this Norse legend goes Thor’s father Hervarar saga ok Heiðreks disguises himself from Odin the king. This riddle was one not to be missed by Thor’s father and he was eventually able to answer it. Odin the King had narrowly escaped and turned into a crow upon him solving it. The riddle goes:

“Four hang, four sprang, two point the way, two to ward off dogs, one dangles after, always rather dirty. What am I?”

The answer is, a cow of which has four feet and four udders, two horns and two eyes, and the tail dangles after.

A unique riddle for a unique purpose

A unique riddle for a unique purpose

They say that this riddle was used by a psychopath doctor to show the mentality of a killer.

“While at the funeral of her own mother, she met a guy whom she did not know. She thought this guy was amazing, so much the dream guy that she was searching for that she fell in love with him immediately. However, she never asked for his name or number and afterward could not find anyone who knew who he was. A few days later the girl killed her own sister. So… Why did she kill her sister?”

The logical and psychopath’s answer would be, “She was hoping the guy would appear at the funeral again.”

Riddles from India

Riddles from India

These deep thinking riddles tease the mind.

“What is it that you will break even when you name it?”

The answer is silence.


“What is put on a table, cut, but never eaten?”

The answer is a deck of cards.


“What goes into the water red and comes out black?”

The answer is, a red hot poker.

Other Ancient Riddles

Other Ancient Riddles

Riddles speak of the pace of life and the mentality of the era. Here are some riddles.

At night they come without being fetched,
“And by day they are lost without being stolen.”
Hint: They belong to the night
The answer is, stars.

“There was a green house.
Inside the green house there was a white house
Inside the white house there was a red house.
Inside the red house there were lots of babies.”

The answer is watermelon.”

Modern riddles

Modern riddles

Modern riddles can also turn the tide on anyone. Here are some not so famous but creative ones.

“There is a pond with white stones along the sides. At the center of the pond is a crocodile. What is this thing?”

The answer is a tongue.


Another would be fitting for school kids.

“When I am clean, I am black. When I am dirty, I am white. What am I?”

The answer is a blackboard.


“Mightily amusing riddles can turn a room from utterly silent to a tumultuous and boisterous party. Riddles evoke the life and love and culture belonging to a specific profession or group of people. From legends to practical stories riddles never fail to push man to his logical senses and limits. Such are what great stories are made of and some riddles too.”

This entry was posted on February 16, 2016.

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