Riddles have roots that run deep into the literary tradition of the West. There is a book called the Exeter Book. It is the largest collection of old English writings. It contains rhymes, puns, and compound words that are used as metaphors in place of single words, or riddles that are in the form of kennings. For example, “the sea” means “whale-rod”.

There are famous riddles that demonstrate a protagonist’s wit in a story or let a character escape some dire situation by using their brains rather than brawn. There are some riddles that play the role of reminding people that there are some questions which cannot be answered. While these can cause unending frustration and head-scratching, the unanswerable questions in the form of riddles make the most strange but pleasant riddles of all.

Top 10 Famous Riddles


Oedipus Rex by Sophocles

This is most likely among the most famous riddles when it comes to Western literature. In this riddle, Oedipus is outside Thebes and is asked the following by the Sphinx.

Riddle: What walks on 4 legs when it is morning, on 2 legs at noon and on 3 legs in the evening?

Answer: Human. As an infant, a man crawls on 4 legs; as an adult he walks on two legs and as an elderly citizen he walks with a cane hence the three legs.


The Hobbit by J.R.R. Tolkien

Bilbo and Gollum were playing a riddle game where Bilbo’s life is at stake. Gollum asks him the following riddle whereby he will be awarded safe passage from the tunnel if he gets it right.

Riddle: This is a thing that is devoured by all things; flowers, trees, beasts, birds; bites steel, gnaws iron; grinds hard stone to meal; beats mountain down, ruins town and slays king. What is it?

Answer: Time.


"The Garden of Forking Paths" by Jorge Luis Borges

Borges's stories are often puzzling. However, this particular story has more of a literal riddle and was used in the explanation of ancient labyrinth by Stephen Albert a Synologist.

Riddle: In a riddle whose only answer is chess, what is the only word that is prohibited?

Answer: Chess.


A House from Sumer

Sumer’s ancient civilization introduced the world to several things including idea of laws, writing and irrigation. They were also behind one of the first examples of riddles. This riddle is said to have been written over 4,000 years back.

Riddle: There is a house. A person enters this house blind but exits it seeing. What is it?

Answer: A school.


Thirty White Horses by J.R.R. Tolkien

J.R.R Tolkien was highly influenced by Norse mythology. He also included several riddles in his writings. In The Hobbit, he challenged Gollum in various riddle competitions in exchange for Gollum’s freedom.

Riddle: There are 30 white horses on a red hill: first they champ, then they stamp, then they stand still. What are they?

Answer: Teeth.


What We Caught from Greece

This riddle is known for its apocryphal involvement with Homer’s death (he was a Greek poet). Homer traveled to Ios Island, which as he had been forewarned by an oracle, would be where he died. On one of his travels along the Island, he came across some fishermen. He asked the fishermen how their day was, and they responded with a riddle. Unfortunately, Homer couldn’t solve the riddle. He refused to leave until he found out the answer to that riddle, which he never did. Eventually, he died on the island.

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

Answer: Lice


Heaven and Hell

This is a riddle that has taken many different forms over the years. However, there is a popular version, and it goes like this.

Riddle: You die then you find yourself in limbo, and you see two doors. One of them leads you to hell and the other one heaven. They are being guarded by two guardians. The guardian guarding the doorway to heaven always tells the truth and the guardian guarding the doorway to hell always lies. What is the one question you will ask to either of the guardians to find out which door will lead you to heaven?

Answer: If I asked the other guardian which door leads to heaven, what would he tell me?


Who Has The Fish? From Albert Einstein

According to tradition, Albert Einstein came up with this riddle when he was a child. While it may not pass as a riddle in the real sense, it still manages to measure one’s focus and intellect.

Riddle: There are 5 houses that have 5 occupants. Each occupant’s house is differently colored. The houses also have different choice of beverages, different cigarette brands, and a unique pet. Your goal is to figure out which occupant owns the fish.

Here is more information:

  • An Englishman resides in a red house

  • The Dane drinks tea

  • Dogs are kept by the Swede

  • The green house is left to the white house

  • The occupant of the green house drinks coffee

  • The birds are kept by the Pall Mall smoker

  • The Dunhill smoker lives in the yellow house

  • The milk is drunk by the man living in the center house

  • The first houses’ occupant is Norwegian

  • The blend smoker’s neighbor keeps cats

  • The horse keeper and the Dunhill smoker live next to each other

  • The German smokes Prince

  • The Norwegian lives right next to the blue house

  • The blend smoker’s neighbor drinks water.

Answer: The German.


Samson’s Riddle from Israel

Samson was more known for the superhuman strength he had than mind. He is the author of one of the most known riddles of all time. During a feast he hosted for his acquaintances, he decided to make a wager. If any of the guests could answer the riddle, he would award them with thirty articles of fine clothing.

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.


The Hardest Logic Puzzle Ever from George Boolos

This riddle is more of a riff of the earlier mentioned "heaven-hell" riddle. It was by George Boolos, but it was inspired by Raymond Smullyan.

Riddle: There is an Island that has 3 gods. One god always tells a lie, and the other always tells the truth. The third god has a random behavior. To top it off, these three gods, being jerks, answer in their own languages such that you are unable to tell which word, between “ja” or “da”, means “no” or “yes”. You have 3 questions to work out the True god, the false god, and the Random god.


Question 1: (To any of the three gods) If I were to ask you "Is that the random god," would your answer be "ja?" (This questions, no matter the answer, will enable you to tell which god is not random i.e. the god who is either False or True)

Question 2: (To either the True or False god) If I asked you "are you false," would your answer be "ja?" 

Question 3: (To the same god you asked the second question) If I asked you "whether the first god I spoke to is random," would your answer be "ja?"


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