99 Hard Riddles (With Answers) That'll Leave You Stumped

When was the last time you challenged yourself with a riddle? These puzzles are a fun way of testing your critical thinking skills, encouraging you to examine your assumptions, look for alternate meanings, and think more creatively. The brain-flexing value of a good riddle doesn't go away as you grow up either — brain teasers can help you stay sharp. They can also make you the life of the party, allowing you to stump even your smartest family and friends. So read on for 99 hard riddles that will get your gears turning. Don't worry, answers are included!

RELATED: 73 Brain Teasers for Adults That Will Definitely Leave You Stumped.

Jump Ahead:

• Hardest Riddles Ever
• Fun Riddles for Kids
• Short, Hard Riddles
• Tricky Riddles for Adults
• Math Riddles for Adults
• Tough Riddles about Words and Linguistics

Hardest Riddles Ever

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1. Riddle: I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?
   Answer: An echo.
2. Riddle: You measure my life in hours, and I serve you by expiring. I'm quick when I'm thin and slow when I'm fat. The wind is my enemy.
   Answer: A candle.
3. Riddle: I come from a mine and am surrounded by wood. I help others to express themselves. What am I?
   Answer: Pencil lead.
4. Riddle: What is brown and has a tail, a head, and no legs?
   Answer: A penny
5. Riddle: If all Wibbles are Criggles, all Borkins are Kwumblins, no Hoggles are Borkins, and all Criggles are Borkins, is it true that all Borkins are Criggles?
   Answer: No.
6. Riddle: What English word has three consecutive double letters?
   Answer: Bookkeeper.
7. Riddle: A bus driver goes the wrong way down a one-way street. He passes the cops, but they don't stop him. Why?
   Answer: He was walking.
8. Riddle: Name the next three letters in this combination: OTTFFSS.
   Answer: ENT. Each represents the first letter of a number in a sequence beginning with "one." So what comes after six and seven? Eight, nine, and ten.
9. Riddle: There came a bird featherless and sat on the trees leafless. There came a maiden speechless and ate the bird featherless, from off the trees leafless. What is it?
   Answer: Snow.
10. Riddle: You don't know me yet, but you always miss me when I'm gone. What am I?
    Answer: Time.
11. Riddle: Poor people have it. Rich people need it. If you eat it you die. What is it?
    Answer: Nothing.
12. Riddle: I can fly but have no wings. I cry but have no eyes. What am I?
    Answer: A cloud.
13. Riddle: Sam is outside a shop. She can't read the signs, but she knows she needs to go in to make a purchase. What store is she at?
    Answer: An eyeglass store.
14. Riddle: What walks on four feet in the morning, two in the afternoon, and three at night?
    Answer: A man. The times of day represent a lifetime. He crawls as a baby, walks as an adult, and walks with a cane as an elderly man.
15. Riddle: The more you try to see me, the less you see. The closer you get, the less you know. I'm everywhere, but I can't be touched. What am I?
    Answer: A shadow.
    

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Fun Riddles for Kids

16. Riddle: I have keys but no locks. I have space but no room. You can enter, but there's no door. What am I?
    Answer: A keyboard.
17. Riddle: Which word in the dictionary is always spelled incorrectly?
    Answer: "Incorrectly."
18. Riddle: It belongs to you, but everyone else uses it.
    Answer: Your name.
19. Riddle: I'm light as a feather, yet the strongest person can't hold me for long. What am I?
    Answer: Your breath.
20. Riddle: What color is the wind?
    Answer: Blew.
21. Riddle: I go up but never down. What am I?
    Answer: Your age.
22. Riddle: Which fish costs the most?
    Answer: A goldfish.
23. Riddle: Where do you take a sick boat?
    Answer: To the dock-tor.
24. Riddle: Who has a neck and no head, two arms and no hands?
    Answer: A shirt.
25. Riddle: You see me once in June, twice in November, and not at all in May. What am I?
    Answer: The letter "E."
26. Riddle: What has a head, a tail, is brown, and has no legs?
    Answer: A penny.
27. Riddle: What has ten letters and starts with gas?
    Answer: An automobile.
28. Riddle: How can you drop a raw egg onto a concrete floor without cracking it?
    Answer: Concrete floors are very hard to crack.
29. Riddle: What has a bottom at the top?
    Answer: Your legs.
30. Riddle: I speak without a mouth, hear without ears, and answers without being alive. What am I?
    Answer: An echo.
31. Riddle: What tastes better than it smells?
    Answer: Your tongue.
32. Riddle: What has four fingers and a thumb but isn't alive?
    Answer: A glove.
33. Riddle: Two fathers and two sons are in a car, yet only three people are in the car. How?
    Answer: They are a grandfather, father, and son.
34. Riddle: What kind of animal can you always find at a baseball game?
    Answer: A bat!

Short, Hard Riddles

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35. Riddle: I have only two words but thousands of letters. What am I?
    Answer: The post office.
36. Riddle: What can travel all around the world while remaining stuck in a corner?
    Answer: A stamp.
37. Riddle: What can you hold in your right hand but never in your left?
    Answer: Your left hand.
38. Riddle: What has many teeth but cannot bite?
    Answer: A comb.
39. Riddle: You go at red and stop at green. What am I?
    Answer: A watermelon.
40. Riddle: How much dirt is in a hole that measures four feet by four feet by five feet?
    Answer: None; holes are empty.
41. Riddle: What can you fill with empty hands?
    Answer: Gloves.
42. Riddle: What disappears the moment you say its name?
    Answer: Silence.
43. Riddle: What kind of coat is best to put on wet?
    Answer: A coat of paint.
44. Riddle: What type of cheese is made backward?
    Answer: Edam.
45. Riddle: What is the one thing everyone can agree is between heaven and earth?
    Answer: The word "and."
46. Riddle: I can make sounds, but I cannot be played. What am I?
    Answer: Your voice.
47. Riddle: I am higher without a head. What am I?
    Answer: A pillow.
48. Riddle: I have 13 hearts but no lungs or stomach. What am I?
    Answer: A deck of cards.
49. Riddle: I am easy to lift but hard to throw. What am I?
    Answer: A feather.
50. Riddle: When is "L" greater than "XL"?
    Answer: When you're using Roman numerals.
51. Riddle: The more you take, the more you leave behind. What are they?
    Answer: Footsteps.

Tricky Riddles for Adults

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52. Riddle: Without a bridle or a saddle, across a thing, I ride a-straddle. And those I ride, by help of me, though almost blind, are made to see. What am I?
    Answer: Eyeglasses.
53. Riddle: George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave are drinking Pepsi. Following this pattern, is Elizabeth drinking coffee or soda?
    Answer: Coffee, just like all the other names with two E's. Those with one "E" drink Pepsi.
54. Riddle: First, think of the color of the clouds. Next, think of the color of snow. Now, think of the color of a bright, full moon. Now, answer quickly: What do cows drink?
    Answer: Water.
55. Riddle: If you have me, you want to share me. If you share me, you don't have me. What am I?
    Answer: A secret.
56. Riddle: David's father has three sons: Snap, Crackle, and _____?
    Answer: David.
57. Riddle: My thunder comes before the lightning. My lightning comes before the clouds. My rain dries all the land it touches. What am I?
    Answer: A volcano.
58. Riddle: I have cities but not houses. I have mountains but no trees. I have coasts but no sand. What am I?
    Answer: A map.
59. Riddle: I am something people love or hate. I change people's appearances and thoughts. If a person takes care of themself, I will go up even higher. Some people might want to try and hide me, but I will show. No matter how hard people try, I will never go down. What am I?
    Answer: Age.
60. Riddle: You're in a dark room with a candle, a wood stove, and a gas lamp. You only have one match, so what do you light first?
    Answer: The match.
61. Riddle: A woman was born in 1975 and died in 1975. At the age of her death, she was 22 years old. How is this possible?
    Answer: 1975 refers to the hospital room number, not the year.
62. Riddle: Four cars come to a four-way stop, each coming from a different direction. They can't decide who got there first, so they all go forward at the same time. All four cars go, but none crash into each other. How is this possible?
    Answer: They all made right-hand turns.
63. Riddle: I have keys but no locks. I have space but no room. You can enter, but you can't go outside. What am I?
    Answer: A computer keyboard.
64. Riddle: A woman shoots her husband. She plunges him underwater for several minutes, then hangs him. Right after, they enjoy a lovely dinner. What happened?
    Answer: She took a picture of him and developed it in her dark room.
65. Riddle: A is the brother of B. B is the brother of C. C is the father of D. So how is D related to A?
    Answer: A is D's uncle.
66. Riddle: A butcher stands six feet and one inch tall and wears size 12 shoes. What does he weigh?
    Answer: Meat.
67. Riddle: 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.
68. Riddle: How can you physically stand behind your father while he is standing behind you?
    Answer: By standing back-to-back with him.

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Math Riddles for Adults

Best Life

69. Riddle: When Billy is asked how old he is, he replies, "In two years, I will be twice as old as I was five years ago." How old is he?
    Answer: 12 years old.
70. Riddle: How is seven different from the rest of the numbers between one and 10?
    Answer: Seven is the only one with two syllables.
71. Riddle: Turn me on my side, and I am everything. Cut me in half, and I am nothing. What am I?
    Answer: The number eight.
72. Riddle: A girl has as many brothers as sisters, but each brother has only half as many brothers as sisters. How many brothers and sisters are there in the family?
    Answer: Four sisters and three brothers.
73. Riddle: Two girls were born to the same mother, on the same day, at the same time, in the same month, and in the same year—but they're not twins. How is this possible
    Answer: The girls are triplets.
74. Riddle: A barrel of water weighed 60 pounds. Someone put something in it, and now it weighs 40 pounds. What did the person add?
    Answer: A hole.
75. Riddle: I am an odd number. Take away a letter, and I become even. What number am I?
    Answer: Seven.
76. Riddle: TEN = 20, 5, 14. MEN = 13, 5, 14. Using the same logic, what do WOMEN equal?
    Answer: WOMEN = 23, 15, 13, 5, 14. The numbers represent the letter's position in the English alphabet.
77. Riddle: What would a math teacher be doing with a piece of graph paper?
    Answer: Plotting something.
78. Riddle: How do eight eights add up to one thousand?
    Answer: 888 + 88 + 8 + 8 + 8 = 1000.
79. Riddle: Mr. Taylor has four daughters and each has a brother. In total, how many children does Mr. Taylor have?
    Answer: Five children because all of his daughters have the same brother.
80. Riddle: If an electric train is moving north at 55 mph and the winds blowing east at 70 mph, which way does the smoke blow?
    Answer: An electric train doesn't emit smoke.
81. Riddle: What is 3/7 chicken, 2/3 cat, and 1/2 goat?
    Answers: Chicago.
82. Riddle: If a zookeeper had 100 pairs of animals in her zoo, and two pairs of babies are born for each one of the original animals, then (sadly) 23 animals don't survive, how many animals do you have left in total?
    Answer: 977 animals (100 x 2 = 200; 200 + 800 = 1000; 1000 – 23 = 977).

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Tough Riddles About Words and Linguistics

Best Life

83. Riddle: I belong in December, but not in any other month. I am not a holiday. What am I?
    Answer: The letter "D."
84. Riddle: One of these words does not belong: Brawl, Carrot, Change, Clover, Proper, Sacred, Stone, Seventy, Swing, Travel.
    Answer: Carrot. It's the only word that does not become another word when you remove the first and last letters.
85. Riddle: White bird, featherless. Flying out of paradise. Flying over sea and land. Dying in my hand. What is it?
    Answer: A snowflake.
86. Riddle: What 5-letter word, if typed in all capital letters, can be read the same upside down?
    Answer: SWIMS.
87. Riddle: How do you spell COW in thirteen letters?
    Answer: SEE O DOUBLE YOU.
88. Riddle: I'm everywhere and a part of everyone. I am at the end of space and time and existence itself. What am I?
    Answer: The letter "E."
89. Riddle: 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."
90. Riddle: 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.
91. Riddle: What comes once in a minute, twice in a moment, but never in a thousand years?
    Answer: The letter "M."
92. Riddle: What is the longest word in the dictionary?
    Answer: "Smiles," because there is a mile between each "s."
93. Riddle: Where is the only place where today comes before yesterday?
    Answer: The dictionary.
94. Riddle: How many letters are in the alphabet?
    Answer: There are 11 letters in the words "the alphabet."
95. Riddle: It cannot be seen, cannot be felt, cannot be heard, cannot be smelt. It lies behind stars and under hills and empty holes it fills. It comes first and follows after, ends life, and kills laughter.
    Answer: Darkness.
96. Riddle: With pointed fangs, I sit and wait; with piercing force, I crunch out fate. I grab victims, proclaiming might, and physically join with a single bite. What am I?
    Answer: A stapler.
97. Riddle: If the prisoner tells a lie, he'll be hanged; if he tells the truth, he'll be beheaded. What can he say to save himself?
    Answer: "You will hang me."
98. Riddle: What English word retains the same pronunciation, even after you take away four of its five letters?
    Answer: "Queue."
99. Riddle: I am a word. If you remove my first letter, I’m still the same. If you remove my last letter, I’m still the same. Even if you remove the middle letter, I’m still the same. What word am I?
    Answer: Empty.

This story has been updated to include additional entries, fact-checking, and copy-editing.