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Difficult Riddles Challenge

Take the 55 Difficult Riddles Challenge and see how you stack up against the best riddle solvers with the scoring key below.

We’ve identified fifty-five of the most difficult riddles that have stood the test of time. Your task is to answer as many as you can correctly without consulting the Internet or other resources. You’ll receive two points for every correct answer.

This challenge will put your critical thinking skills, logic ability, and general intelligence to the test. If you can’t come up with a good answer, just move on to the next difficult riddle.

Are you up for the challenge? Ok, let’s begin. Good luck – You’re probably going to need it.

Really Hard Riddles

1.) Mount Everest was discovered in 1852. Before it was discovered, what was the tallest mountain?
Answer: Still Mount Everest. (This is one of those riddles that makes you kick yourself if you couldn’t come up with the correct answer.)

What was the tallest mountain before Mount Everest was discovered riddle.

2.) You are in a room with three monkeys. One has a banana, one has a leaf, and one has a stick. Who is the smartest primate in the room?
Answer: Well, you are. Humans are primates. (For any riddle that leads with the word “you,” be ready for a solution that involves you, your name, or your age.)

Smartest primate in the room riddle.

3.) A dog, Max, is tied to a 15-foot rope. Max’s food dish is 25 feet away. And yet, Max is still able to eat from his dish. How did Max do it?
Answer: One end of the rope was tied to Max, but the other end wasn’t tied to anything. (This is the type of riddle that leads readers to make an unneeded assumption.)

4.) What has two arms but no hands, no eyes, but can help you see?
Answer: Glasses. (If you focused on “help you see,” you probably got to the right answer.)

5.) It is black when you purchase it, red when you use it, and gray when you throw it away? What is it?
Answer: Charcoal. (Even for folks who grill out a lot, this is a tough riddle. If they were easy, they wouldn’t make our list.)

Difficult Riddles with answers.

Put your Thinking Cap On

6.) The more you remove from it, the bigger it grows. What is it?
Answer: A hole. (Of course, this makes total sense. I just wish I’d come up with the answer the first time I was asked.)

7.) Is a vintage one-hundred-dollar bill more valuable than a new one?
Answer: Yes. $100 is always greater than $1. (A little play on words is fair game.)

8.) This starts with a t, ends with a t, and is filled with tea. What is it?
Answer: A teapot. (Even though not too many things are filled with tea, this still is a tough one.)

9.) You’re driving in a Toyota Camry. You make a right-hand turn. Which of your tires do not move?
Answer: Your spare tire. (Ugh! Some might suggest this should be in the hard riddles for adults section.)

10.) What do a tiger, comb, and zipper all have in common?
Answer: Teeth. (As there are not too many words associated with a comb or a zipper, hopefully, this one was a little easier for you.)

If you like these riddles, you might be interested in seeing our full list of riddle pages.

Hard Riddles With Answers

11.) It has keys but no locks. It has space but no room. You can enter but can’t go inside. What is it?
Answer: A keyboard.

12.) What English word has three consecutive double letters?
Answer: A bookkeeper.

13.) It can’t be seen, heard, or smelt. It lies behind stars and under hills and any empty holes it fills. And it comes early and follows after, ends life, and kills laughter. What is it?
Answer: Darkness.

14.) A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Afterward, they enjoy a lovely dinner. How can this be?
Answer: She took a photograph of him and developed it in her darkroom.

15.) What word in the English language does the following: the first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?
Answer: Heroine.

You might like All of our Riddles page.

Tougher as Nails

16.) Emma stands on one bank of a river, and her dog Bandit stands across on the other bank. Molly calls for Bandit. Bandit comes and is not wet at all. Bandit didn’t use a bridge. How can this be?
Answer: It’s wintertime in a cold climate, and the river is frozen. Bandit walked across the frozen river without getting wet.

17.) A sundial tells time and has the fewest moving parts of any time-telling device. What timepiece has the most moving pieces?
Answer: An hourglass – it has thousands of grains of sand.

18.) I am a person, a bird, and a fruit; what am I?
Answer: A Kiwi. A person from New Zealand is a Kiwi.

See The World’s Hardest Riddles to test your smarts.

Hard riddles chart.

Logic Puzzles

19.) What can you hold in your right hand but never in your left?
Answer: Your left hand.

20.) I threw a ball as hard as I could, and it came right back to me. And yet I didn’t bounce it off of any wall or anything. How could this be?
Answer: I three the ball straight up in the air.

21.) What is always hot, even if stored in a refrigerator?
Answer: Tabasco sauce.

22.) Which word in the dictionary is always spelled incorrectly?
Answer: Incorrectly.

23.) A mother had two daughters were born on the same day in the same year at the same hour. But they were not twins. How could this be?
Answer: They were two of three triplets or two of four quadruplets.

24.) What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
Answer: The letter “r.”

Challenging brain teasers and difficult riddles.

Tough Brainteasers

25.) What English word retains the same pronunciation, even after you remove four of its five letters?
Answer: Queue.

26.) George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave< are drinking soda. Using logic, is Elizabeth drinking coffee or soda?
Answer: Elizabeth is drinking coffee. The letter “e” appears twice in her name, as it does in the names of the others that are drinking coffee.

27.) I am higher without a head than I am with it. What am I?
Answer: A pillow.

28.) I jump when I’m walking and stand when I’m sitting. What am I?
Answer: A kangaroo.

See riddles for adults with answers.

Difficult Riddles

29.) Arthur fell off a 30-foot ladder after hanging Christmas lights on the house and yet didn’t get hurt. How could this be?
Answer: Because he fell of the bottom rung.

30.) I am the beginning of everything, the end of time and space, the beginning of every end, and the end of every place. What am I?
Answer: The letter “e.”

31.) You are in Simon’s house where there is one rule that can’t be broken. You can have pizza, but you cannot have a sandwich. And you can use pepper but not salt. You can leave by the front door, but it isn’t an exit. What is the rule at Simon’s house?
Answer: Only things with double letters are permitted. (See what I did there with “letters” and “permitted”?)

32.) What goes up the chimney down but cannot go down the chimney up?
Answer: An umbrella.

33.) Three different doctors said that Paul is their brother, yet Paul claims he has no brothers. Who is lying?
Answer: No one is lying because the three doctors are Paul’s sisters.

34.) What flies through the air on stolen feathers?
Answer: An arrow.

35.) In Denver, you cannot take a photo of a man with an artificial hip. Why not?
Answer: You need a camera!

36.) What tastes better than it smells?
Answer: Your tongue.

37.) What sport is played worldwide has four letters and begins with a “T”?
Answer: Golf – you see, a golf tee is where the ball is placed on an opening drive.

What vegetable is only sold fresh?

Math Riddles for Kids

38.) What happens once in soccer, twice in football, but never in baseball?
Answer: The letter o.

39.) What is unique about this sequence of numbers: 8-5-4-9-1-7-6-3-2-0?
Answer: The numbers are in alphabetical order

40.) How many letters are there in the alphabet?
Answer: 11. “The Alphabet” features eleven letters.

41.) How many birthdays does the average person have?
Answer: One birthday. Everyone has just one birthday.

42.) I have two heads and two tails and walks around on four legs. What am I?
Answer: A girl with a ponytail riding a horse.

Funny Riddles

43.) Three football players – an offensive tackle, a linebacker, and the tight end – were standing under an umbrella and yet didn’t get wet. How could that be?
Answer: It wasn’t raining outside.

44.) Emma was practicing for the Olympics. She jumps 152 feet, all on her own. She lands unhurt and makes the team. How did she do it?
Answer: She was a ski jumper.

45.) First, think of the color of the clouds. Next, think of the color of the snow. Now, think of the color of a bright, full moon. Now, answer quickly: What do cows drink?
Answer: Water.

46.) If you are traveling south on an electric train, which way is the smoke from the train going?
Answer: There is no smoke – it’s an electric train.

47.) How can you drop a raw egg onto a concrete floor without cracking it?
Answer: Well, concrete floors are very strong. It’s quite unlikely that the force of a fallen egg would crack the flooor.

48.) Where is the only place where today comes before yesterday?
Answer: The dictionary.

49.) If you paint a white house blue, it will become blue. If you color a picture of an orange, it is orange. And if you throw a scarf into the Red Sea, what will it become?
Answer: Wet.

50.) How many legs does a cow have if you call its ears legs?
Answer: Four legs. Just because you call its ears legs doesn’t make them legs.

Best Riddles for kids.

Critical Thinking Questions

51.) What vegetable is only sold fresh – never canned, frozen, in jars, or pickled?
Answer: Lettuce.

52.) CAUTION: SCHOOL CROSSING — Can you spell that without any Os?
Answer: T-H-A-T!

53.) Which letter comes next in this sequence: J-F-M-A-M-J-J-A-S?
Answer: O. O for October. Each is the first letter of the months of the year, January, February, March…

54.) Joe’s speed boad is at dock. The boat has a ladder over the side that nearly touches the water. The rungs are 12 inches apart. How many rungs are underwater during high tide when the waiter raises 15 inches?
Answer: None. The boat floats and rises when the water rises.

55.)A carrot, five buttons, and a scarf are found in front of a Minnesota house on a spring morning. What is the reason?
Answer: They were part of a snowman that melted.

Scoring Key

Well, how did it go?

Remember you receive two points for every correct answer. With 55 questions, there’s a high score possibility of 110 points.

Let’s face it; this is a tough challenge. Since we know these are challenging questions, our strict scoring guidelines have been eased. See below.

80 + points = Prodigy. Harvard would be too easy for you.

60 – 79 points = Genius. The Nobel Prize is within your reach.

40 – 59 points = Super smart. “A” grades come easy to you.

20 – 39 points = Really smart. Just answering ten of these bad boys shows us you know what you’re talking about.

< 20 points = Keep at it. You’re still probably crushing it at school.

The mere fact that you took on this challenge suggests you’re smarter than most. It shows you’re trying to improve yourself. So congratulate yourself and read some tips below on how to solve hard riddles.

Tips For Solving Difficult Riddles

Here are some tips for solving tough, critical-thinking riddles.

A.) Read the question over slowly several times. Upon your second, third, or even later reading, a clue might expose itself.

B.) Many challenging riddles are written in hopes that the readers will make an incorrect assumption. Assume nothing, e.g., just because an umbrella is out doesn’t mean it’s raining.

C.) Sometimes, the question itself has a false premise, e.g., roosters don’t lay eggs, or electric trains don’t generate smoke. Be on the lookout for false beliefs.

D.) Think creatively. Don’t zero in on an obvious answer. Consider many options before making your answer.

E.) Many of these tough riddles are essentially trick questions. The way the question is written sends you down a suggested path. When considering all answer possibilities, try rejecting that path, and come up with the solution just based on the facts given.

Challenging Riddles FAQ

Here are some frequently asked questions about challenging riddles.

What is the hardest “What Am I?” riddle?

I have two heads and two tails and walk around on four legs. What am I? Answer: A girl with a ponytail riding a horse.

What is a difficult riddle for kids?

A carrot, five buttons, and a scarf are found in front of a Minnesota house on a spring morning. What is the reason? Answer: They were part of a snowman that melted.

What is a difficult riddle for teens?

Which letter comes next in this sequence: J-F-M-A-M-J-J-A-S? Answer: O. O for October. The sequence lists the first letter of the months of the year, January, February, March, etc.

By Mike O’Halloran

Mike is the founder and editor of Greeting Card Poet. He has cowritten four books on kids trivia.


You are on our 55 Difficult Riddles Challenge page.

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