50 Riddles With Answers for a Serious Mental Workout

There’s nothing like a good riddle to twist your brain into knots and to provide a satisfying zing when you solve it correctly. Riddles can offer entertainment and fun while also giving your brain something genuinely hard to work on. As it turns out, these enigmatic, often extremely frustrating (yet shockingly obvious when you know the answer!) questions have actually been confounding humans for thousands of years.

Famous Riddles in History

Riddles have a very long history. In many myths, heroes encounter ancient beasts or guardians who force them to answer tricky questions in order to pass. This is the case for the Greek tragic hero Oedipus, who famously defeats the winged Sphinx by solving her riddle, and thus saves his own life—for the time being.

In some versions of the story, the question she asks is: “What goes on four feet in the morning, two feet in midday, and three feet in the evening?” Oedipus ultimately provides the correct answer, which is: “Man.” Upon being bested, the Sphinx throws herself to her death.

Another millennia-old reference to riddles appears in the biblical story of Samson. In this tale, Samson shares a riddle with his Philistine companions at his wedding celebration and promises to give them clothes if they succeed. The puzzle he poses is as follows: “Out of the eater came something to eat; out of the strong came something sweet.”

The men eventually coerce Samson’s bride into telling them the answer: “What is sweeter than honey, and what is stronger than a lion?” Samson’s riddle references a time when he killed a lion, then returned to find that a swarm of bees had produced honey in its carcass, which he then served to his unwitting parents.

Fortunately, if you’re reading this, you aren’t facing the threat of death at the hands of a monstrous, self-destructive hybrid creature. You likely aren’t a desperate wedding guest, either (though that is slightly more in the realm of possibility), or someone who has eaten honey out of a dead lion.

Instead, these riddles are perfect for testing your mental fortitude or confounding your friends and family at your next social gathering. Still, it might raise the stakes a bit to imagine that you’re standing before an imposing mythical monster while reading these quandaries. Some of these might also make you think of the world in entirely new ways. How swiftly can you solve these tricky riddles?

50 Riddles With Answers

Riddle: What can you put in a bucket to make it weigh less?

Answer: A hole.

Riddle: What has a face and two hands but no arms or legs?

Answer: A clock.

Riddle: What gets bigger the more you take away from it?

Answer: A hole.

Riddle: What has a head, a tail, is brown, and has no legs?

Answer: A penny.

Riddle: What word contains 26 letters but only has three syllables?

Answer: Alphabet.

Riddle: What can go up a chimney down but can't go down a chimney up?

Answer: An umbrella.

Riddle: What has a lot of eyes but cannot see?

Answer: A potato.

Riddle: What has one head, one foot, and four legs?

Answer: A tennis ball.

Riddle: What can you serve but never eat?

Answer: A tennis ball.

Riddle: What can you make that nobody—not even you—can see?

Answer: Noise.

Riddle: What has a bottom at the top?

Answer: Your legs.

Riddle: What is easy to get into but hard to get out of?

Answer: Trouble.

Riddle: A girl fell off a 20-foot ladder but wasn't hurt. Why?

Answer: She fell from the bottom rung.

Riddle: A woman has four daughters, and each daughter has a brother. How many children does the woman have?

Answer: Five.

Riddle: If two's company and three's a crowd, what are four and five?

Answer: Nine.

Riddle: A man has 17 sheep. All but nine run away. How many are left?

Answer: Nine.

Riddle: If you have three apples and you take away two, how many do you have?

Answer: Two.

Riddle: A doctor gives you three pills and tells you to take one every half hour. How long will the pills last?

Answer: One hour.

Riddle: What keeps something that cannot be kept?

Answer: A clock.

Riddle: Three brothers run a never-ending race. One is slow, one is steady, and one is fast. Who are they?

Answer: The hour, minute, and second hands of a clock.

Riddle: I am a five-letter word. Remove my first letter and I become a form of energy. Remove my first two letters and I become something needed to live. Rearrange my final three letters and you can drink me. What am I?

Answer: Wheat. Remove the W to get heat, remove the H to get eat, and rearrange the final three letters to get tea.

Riddle: What word begins with T, ends with T, and has T inside it?

Answer: Teapot.

Riddle: What starts with E, ends with E, but contains only one letter?

Answer: An envelope.

Riddle: What has a tongue but cannot talk?

Answer: A shoe.

Riddle: What can you hear but not touch or see?

Answer: Your voice.

Riddle: What has 13 hearts but no other organs?

Answer: A deck of cards.

Riddle: Three doctors say that Robert is their brother. Robert says he has no brothers. How can everyone be telling the truth?

Answer: 2005 was the number of the house in which he was born and died.

Riddle: A man was born in 2005 and died in 2005 at age 80. How is that possible?

Answer: 2005 was the number of the house in which he was born and died.

Riddle: Five machines take five minutes to make five widgets. How long would 100 machines take to make 100 widgets?

Answer: Five minutes.

Riddle: A farmer has 15 apples. All but eight are eaten. How many apples does the farmer have left?

Answer: Eight.

Riddle: A man pushes his car to a hotel and immediately realizes he's bankrupt. Why?

Answer: He's playing Monopoly.

Riddle: Two fathers and two sons go fishing. Each catches one fish, yet they bring home only three fish. How is that possible?

Answer: There are only three people: a grandfather, his son, and his grandson.

Riddle: A woman has two children born at exactly the same time, on the same day, in the same year. They aren't twins. How is that possible?

Answer: They're two of a set of triplets.

Riddle: Without looking at a calendar, can you name a month that has exactly 28 days?

Answer: February in a non-leap year.

Riddle: A man is running a race. He passes the person in second place. What position is he in now?

Answer: Second place.

Riddle: An electric train is traveling west at 60 miles per hour while a strong wind blows east at 40 miles per hour. Which direction does the train's smoke travel?

Answer: Nowhere. An electric train doesn't produce smoke.

Riddle: A monkey, a squirrel, and a bird race to the top of a coconut tree. Who gets to the banana first?

Answer: None of them. Coconuts don't grow bananas.

Riddle: How many months have 28 days?

Answer: All 12 months.

Riddle: Where does today come before yesterday?

Answer: The dictionary.

Riddle: I have no life, but I can die. What am I?

Answer: A battery.

Riddle: It is the beginning of eternity, the end of time and space. It is the start of every end, the end of every place.

Answer: The letter E.

Riddle: What lives if you feed it, but dies if you give it a drink?

Answer: Fire.

Riddle: What can you drive that has wheels and also flies?

Answer: A garbage truck.

Riddle: What can run but never walks, has a mouth but never talks, has a bed but never sleeps, and has a head but never weeps?

Answer: A river.

Riddle: A plane crashes on the border of the U.S. and Canada. Where do they bury the survivors?

Answer: You don't bury survivors.

Riddle: What has a neck but has no head?

Answer: A guitar.

Riddle: What word is pronounced the same if you take away four of its five letters?

Answer: Queue.

Riddle: What has many keys but can’t open any locks?

Answer: A piano.

Riddle: What is so fragile that saying its name breaks it?

Answer: Silence.

Riddle: Why is it that when you have lost something, it’s always in the last place you look?

Answer: Because you stop looking when you find it.