Much like puns, riddles are so much more delightful if you have someone to tell them to, to be able to watch their face as they’re stumped, or as they begin to work out the answer.

If you’re always on the hunt for a good riddle, here are a bunch you might not have heard before now.

1. A hat of a different color.

Four men walk into the desert. Suddenly all four are simultaneously knocked out.

They awake buried to their heads in the sand unable to look anywhere but straight ahead.

They are positioned so that each man sees another’s head before him. However between the first and second man there is a separating wall. So the first man sees only desert. The second man sees only wall.

The third man sees another’s head and a wall.

The fourth man sees two heads and a wall. On top of each mans head is a hat. The underside of each cap is black, but the outside of each cap is either blue or white. Before any of the men can speak, their captors tell them if they speak, they d**.

However, if any of them can guess the color of their cap on the first try they can all go free. The captors tell them that there are two blue caps and two white caps.

After a minute, the third man says his hat correctly and they are all free. How did he know?

Answer: If the last man saw 2 blues or 2 whites, he would know his colour and would have said it immediately. However, since he did not say, he is unsure because he saw 1 blue and 1 white.

The 3rd man now knows about this after sometime. If the 3rd man sees white, then he will know his is blue, and vice versa.

2. What’s in a word?

‘Tis a very ugly word,

And one that makes one shudder,

Whenever it is heard.

It mayn’t be very wicked;

It must be always bad,

And speaks of sin and suffering,

Enough to make one mad.

They say it is a compound word,

And that is very true;

And then they decompose it,

Which, of course, they’re free to do.

If, of the dozen letters,

We take off the first three,

We have the nine remaining,

As sad as they can be;

For though it seems to make it less,

In fact it makes it more,

For it takes the brute creation in,

Which was left out before.

Let’s see if we can mend it –

It’s possible we may,

If only we divide it,

In some new-fashioned way.

Instead of three and nine, then,

Let’s make it four and eight,

You’ll say it makes no difference,

At least not very great;

But only see the consequence!

That’s all that need be done,

To change this mass of sadness,

To unmitigated fun.

It clears off swords and pistols,

Revolvers, Bowie-knives,

And all the horrid weapons,

By which men lose their lives.

It wakens holier voices –

And now joyfully is heard,

The native sound of gladness,

Compressed into one word!

Yes! Four and eight, my friends!

Let that be yours and mine,

Though all the hosts of demons,

Rejoice in three and nine.

Answer:  Manslaughter

13. On the flip side.

Rich people need it, Poor people have it, And if you eat it you will die.

Answer: Nothing

3. It’s not the future.

What has four wheels and flies?

Answer: A garbage truck

4. Dollars and cents.

Three guests check into a hotel room. The manager says the bill is $30, so each guest pays $10. Later the manager realizes the bill should only have been $25. To rectify this, he gives the bellhop $5 as five one-dollar bills to return to the guests.

On the way to the guests’ room to refund the money, the bellhop realizes that he cannot equally divide the five one-dollar bills among the three guests. As the guests aren’t aware of the total of the revised bill, the bellhop decides to just give each guest $1 back and keep $2 as a tip for himself, and proceeds to do so.

As each guest got $1 back, each guest only paid $9, bringing the total paid to $27. The bellhop kept $2, which when added to the $27, comes to $29. So if the guests originally handed over $30, what happened to the remaining $1?

Answer: The $2 shouldn’t be added to the $27; they’re already part of the $27; $25 for the rooms, $2 for the bellhop.

5. A strange coincidence.

James went skydiving by his house in Utah and, as a result, saved the life of his brother, Jeff. Strangely, Jeff lived in Delaware, and hadn’t spoken to his brother James in years.

What happened?

Answer: James d**d and became an organ donor to sick brother, Jeff.

6. Don’t write it down.

Totally solve-able, but try to do it without writing it down or using outside resources. This is best done strictly verbal. You have a 3 gallon bucket and a five gallon bucket and an unlimited supply of water.

You must get EXACTLY four gallons in one of the buckets, or you will be executed. You have no other way of measuring the water, and no other tools, aside from the two buckets.

How do you achieve precisely 4 gallons?

Answer: Fill the 5 gallon bucket. Pour the water from the 5 gallon bucket into the 3 gallon bucket. When the 3 bucket is full you’ll have exactly 2 gallons remaining in the 5 bucket. Empty the 3 bucket. Pour the 2 gallons from the 5 bucket into the 3 bucket.

Fill the 5 bucket again. Pour from the 5 bucket into the 3 bucket. Since the 3 bucket already has 2 gallons in it, it can only take 1 gallon from the 5 bucket, leaving 4 gallons remaining in the 5 bucket.

7. My grandpa’s favorite, too.

2 coins add up to $0.30

One of them is not a Nickel. What are the 2 coins?

Answer: A Quarter and a Nickel. One of them is not a Nickel, the other one is!

8. No pet left behind.

A farmer has a stray dog, a chicken, and a bag of grain he’s taking to his farm. He gets to the river he needs to cross to get to the farm, but his canoe will only fit one item other than himself.

He can’t leave the dog alone with the chicken or it will eat the chicken, he can’t leave the chicken alone with the grain or it will eat the grain, and the same rules apply on the other side of the river because the farm is still a few miles away.

How does he get everything across the river?

Answer: Chicken over

Go back and bring the dog over.

On the way back take the chicken with you leaving the dog in the right side.

Leave the chicken on the wrong side and take the grain back to the right side.

Then leave the grain with the dog and go back to get the chicken. Or just train your animals

9. This doesn’t sound pleasant.

What’s a thing that’s large and round,
Oft mistaken for a hound,
Known distinctly throughout town,
For the the stench emitted from its mound?

Answer: yo mama

10. Across the desert.

You’re at the edge if a desert and want to cross it. Crossing will take 6 days. You can only carry 4 days worth of food and water, you can hire helpers, but they in turn can also only carry 4 days of food and water.

What is the smallest amount of helpers you need to safely cross (and have everyone survive) and how do you do it?

Answer: you need 2 helpers. After the first day you send 1 helper back with 1 supply of rations, the other 2 are divided between you and the other helper. Now you both have 4 days worth of rations.

The next day you send the 2nd helper back with 2 days of rations, taking the 3rd one yourself. You now have 4 days worth of rations for the remaining 4 days.

11. The right question.

You are in a room with 2 Doors, only one leads to freedom! There are also 2 people who look exactly the same, one of them is always lying and the other on is always telling the truth, you can only ask one question too escape from the room ( you don’t know which one is lying and which one is telling the truth )

what would you ask them?

Answer: I want to be free, which door would the other person show me? Then pick the other door.

12. Everyone loves to anger their friends.

A group of people with assorted eye colors live on an island. They are all perfect logicians — if a conclusion can be logically deduced, they will do it instantly. No one knows the color of their eyes. Every night at midnight, a ferry stops at the island. Any islanders who have figured out the color of their own eyes then leave the island, and the rest stay. Everyone can see everyone else at all times and keeps a count of the number of people they see with each eye color (excluding themselves), but they cannot otherwise communicate. Everyone on the island knows all the rules in this paragraph.

On this island there are 100 blue-eyed people, 100 brown-eyed people, and the Guru (she happens to have green eyes). So any given blue-eyed person can see 100 people with brown eyes and 99 people with blue eyes (and one with green), but that does not tell him his own eye color; as far as he knows the totals could be 101 brown and 99 blue. Or 100 brown, 99 blue, and he could have red eyes.

The Guru is allowed to speak once (let’s say at noon), on one day in all their endless years on the island. Standing before the islanders, she says the following:
“I can see someone who has blue eyes.”

Who leaves the island, and on what night?


Who leaves the island? All of the blue-eyed islanders

On what night(s)? On the 100th night

13. Sounds like dinner.

Two fathers and two sons went fishing. They each brought back a fish, but there are only three fish.

How is this possible?


A grandfather, a father and a son.

Father is both a father AND a son. So four titles for three people.

14. A visit that can’t wait.

A man who is mute decides to take a train to visit his cousin for the day. At the station, he sees that a round trip ticket is $1 while a one way ticket is 50 cents. Without signing with his hands, nor pointing at the price sign, he gives a dollar to the teller, who gives him a round trip ticket.

How did the teller know he wanted a round trip ticket, and not a one way with 50 cents change?

Answer: He paid with coins such that 50c was a subset of the coins (ie in the UK, it’d be two 50p pieces, maybe he paid in your country with four 20c and two 10c coins).

The teller can see that if he’d wanted one-way, he could have handed over just some fo the coins and no change would be needed.

15. Don’t make it harder than it has to be.

Simon’s dad has 4 sons: March, April, and may.

Who’s the fourth son?

Answer: Simon

16. Hungry beast.

I breathe, yet am not alive, My licks are never those of love, The more you feed me, the hungrier I become.

What am I?

Answer: Fire

17. The L word.

There exists a word with L in the middle, in the beginning, and at the end. Yet the word only has 1 L.

What’s the word?

Answer: Inland

18. Not so simple.

A man is running down a hallway. A light flickers and he slows to a walk. What’s happened?

Answer: He’s trying to make it to a prison to present evidence that a man on d**th row was innocent/stop him from being executed, but he sees the light flicker from the surge of them activating the electric chair so he knows he’s too late and the prisoner was already executed??

19. I’m not sure how true this is, but.

Everyone wants one, but once you have it, you want to give it away.

Answer: A secret

20. The only possible answer.

What is greater than God, more evil than the devil and if you eat it – you d**?

Answer: Nothing

21. This one stumped me.

I have four arms, six legs, spit acid and yet everyone wants me.

What am I?

Answer: A liar

22. Abstract enough to drive people nuts.

You’re trapped in a fully enclosed room with no windows and no doors. It is impossible to break through or dig under the walls. The only things you have in the room are a mirror and a table.

How do you escape?

Answer: You look in the mirror, see what you saw. Take the saw, cut the table in half. Two halves make a whole, climb out the hole.

23. I’m officially deceased.

Disclaimer: This riddle needs to be spoken, not written. Reading it here will give it away.

Two penguins are kayaking through the desert. One turns to the other and says, “Where’s your paddle?” The other replies, “Sure does.”

From experience, people go nuts trying to figure out why that’s the response. Just repeat the whole thing to them while they try to figure it out.

Answer: (The answer is, the first penguin is actually saying, “Wears your paddle.” Trying to paddle a kayak through the desert sand really wears down your paddle.)

24. This one will get you.

What’s brown and rhymes with snoop?

Answer: Dr. Dre

25. A classic for a reason.

A cowboy rides into town on Sunday and stays for two days and nights and leaves on Friday. How did he do it?

Answer: His horse is named Friday.

26. Either way.

A man walks into a bar asking for water. The bartender looks at him for a moment and fires a gun into the ceiling. A little bit surprised the man thanks the bartender and walks out. What the heck was happening?

Answer: The man in question had hiccups. The shock of the gunshot cured them for him

27. Not a trick question.

You’re on a game show with three doors. Only one has a prize. You pick Door 3. They show you Door 2 (which they know) is empty.

Do you stay with Door 3, or switch to Door 1?

Answer: Switching doors gives you a higher probability of success. This is the Monty Hall Problem.

28. I love this one.

What rooms have no walls?

Answer: Mushrooms

29. Too many prisoners.

Four prisoners are arrested for a crime, but the jail is full and the jailer has nowhere to put them. He eventually comes up with the solution of giving them a puzzle so if they succeed they can go free but if they fail they are executed.

The jailer puts three of the men sitting in a line. The fourth man is put behind a screen (or in a separate room). He gives all four men party hats. The jailer explains that there are two black and two white hats; that each prisoner is wearing one of the hats; and that each of the prisoners is only to see the hats in front of them but not on themselves or behind. The fourth man behind the screen can’t see or be seen by any other prisoner. No communication between the prisoners is allowed.

If any prisoner can figure out and say to the jailer what color hat he has on his head all four prisoners go free. If any prisoner suggests an incorrect answer, all four prisoners are executed. The puzzle is to find how the prisoners can escape, regardless of how the jailer distributes the hats.


The 3rd prisoner, seeing 2 black/white hats, will know that his is white/black and will say immediately.

If the 3rd prisoner sees 1 black and 1 white, he will stay quiet for some time. The 2nd prisoner will notice that and realise that he and the 1st prisoner has a black and white each. The 2nd prisoner who can see white/black on the 1st prisoner will deduce that his own hat is black/white respectively.

30. An oldie but a goodie.

What is red, but smells like blue paint?

Answer: Red paint

31. 99 people, 1 problem.

You and 99 other people are kidnapped and placed in solitary confinement for an indefinite amount of time, having no way to communicate with the others.

You will all either gain your freedom or be put to d**th depending on if you can answer the kidnappers correctly.

Each hour, one person at random (you are also in the random mix of 100 total people) is taken into a room with two switches that resemble light switches. They are face-up on a table. There is nothing else in the room. There’s nothing to write with and no possible way to communicate with anyone else by any means like writing in the walls or anything like that. You are required to flip one of the switches when brought to the room, no matter what. After you flip the switch, you get escorted back to your solitary confinement. Also, you can only flip one of them each time you get taken into the room.

Being selected at random, the same person can go twice in a row, or three or four or 50 times in a row (who knows right? It’s random).

You must tell the captors when all 99 have been through the room in order to gain your freedom. You only have one opportunity and if you guess correctly, you are given your freedom. If you guess incorrectly, you get out to d**th.

You have 15 minutes to plan with the other 99 so that they have the same plan as you to know when everyone has been through. How do you do it?

Answer: One person is designated as the leader, only they may flip the first switch down. Each person when going into the room will look at the first switch, and flip it up if it is their first or second time seeing the switch down (more on this later).

The leader keeps track of how many times he has flipped the first switch down, and once he gets to a total twice the number of people who are not leader, so in this case, 198. The reason that each person does it twice is to prevent the possibility that any given person is never selected to go in the room and the switch happens to be up initially.

In that scenario the leader would’ve switched it 99 times without said person ever visiting the room, however with 198, the issue with the switch being up to start is negated because having flipped it up an extra time past the 196 mark (98×2), the leader knows person 99 has visited at least once

I’m definitely going to memorize a few of these for future use.

What’s your favorite riddle? If it’s not here, share it with us in the comments!