Riddle Me This: Famous Riddles With Answers

Woman thinking with finger on chin

by Christine Scott |
Updated on

Riddles are one of those things that my brain never seems to retain. I hear them, I appreciate them, and then they promptly leave my headspace. Which means I am pleasantly surprised by them again and again when I hear them further down the line. A bit like a goldfish.

I asked my Puzzles HQ colleagues for a reminder and they were happy to oblige. Before we take a look at some of their favourites, let’s begin with a few of the most famous riddles of all time.

The riddle of the Sphinx

Riddles have been delighting people for thousands of years. This one was first answered correctly by Oedipus in Oedipus the King from the fifth century BC. The Sphinx was so fed up that he solved it and she didn’t get to eat him, that she inexplicably chucked herself into the sea instead and drowned.

Which creature walks on four legs in the morning, two legs in the afternoon, and three legs in the evening?

Answer: A human. They crawl on all fours as a baby, walk on two feet as an adult, and then walk with a cane as an elderly person.

The Riddler’s riddle

Slightly less literary this one, but we couldn’t not feature the actual Riddler – with a teaser that he poses to his old foe Batman in Batman Forever

Tear one off and scratch my head, what was red is black instead.

Riddler from Batman holding question mark cane

Answer: A matchstick.

Deciphering Die Hard

Next there’s Die Hard with a Vengeance. The riddle which features in the blockbuster actually originated as a nursery rhyme in the 17th century. It’s now best known as the riddle Bruce Willis and Samuel L Jackson had to solve to stop a bomb going off…

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?

St Ives

Answer: One.

‘Maths!’ I hear you cry in horror (just me?), but no, if the man was going to St Ives, the people he met on the road would have been returning… Trickery.

Potter puzzle

Harry Potter encounters a sphinx (What else? They get everywhere) in the Triwizard Tournament in Harry Potter and the Goblet of Fire, and J K Rowling really thought about this one…

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?

Harry Potter crest

Answer: Spider.

The first part is ‘spy’, the second is ‘d’ and the third ‘er’. Sound them out together and you get (spoiler) the creature who is about to jump out at Harry in the maze.

Ring riddles

And, in probably the most famous riddle-off in literary memory… It’s Gollum vs Bilbo. Here are two. They’re too good to edit:

Alive without breath,
As cold as death;
Never thirsty, ever drinking,
All in mail never clinking.

Answer: A fish.

A box without hinges, key, or lid,
Yet golden treasure inside is hid.


Answer: Eggses.

Puzzles HQ picks

Hungry for more? Find some of our picks below:

1. I have no doors but I have keys, I have no rooms but I have space, you can enter but you can’t leave! What am I?

2. What gets wetter and wetter the more it dries?

3. Which word in the dictionary is spelled incorrectly?

4. What can run but never walks, has a mouth but never talks, has a head but never weeps, has a bed but never sleeps?

5. What can you hold in your left hand but not in your right?

6. What does man love more than life, hate more than death or mortal strife; that which contented men desire; the poor have, the rich require; the miser spends, the spendthrift saves, and all men carry to their graves?

Keep scrolling for the answers. Plus, if you like riddles it’s high time you investigated a cryptic, the famously enigmatic crossword. Find some of our favourite clues here:

Cryptic Crosswords: A Few Of Our Favourite Clues

Favourite Cryptic Crossword Clues box image

1. A computer keyboard (We stare at these a lot).

2. A towel.

3. Incorrectly.

4. River.

5. Your right elbow.

6. Nothing.

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