100+ Hard Riddles That Will Make You Think Twice

Jim Carrey’s The Riddler may have worn an iconically ugly suit in Batman Forever, but he did leave us with the memorable “Riddle me this, riddle me that” quote. Funny enough, the best time to use that line is during family game night when you pull out our list of the hardest riddles ever collected. Stump your friends and family with riddles that run the gamut from funny to thoughtful, and everything in between.

After all, brain teasers aren’t just good for getting in a laugh as you watch your loved ones spin their wheels. Riddles exercise both sides of your brains, which helps keep your brain sharp longer. Because they require unconventional thinking, they also improve important cognitive skills such as problem-solving and the ability to learn.

With that in mind, read through this list of riddles and see how many you get right! Anything above 20 means you’re a certified genius (or at least really, really smart) in our books. No, really. That’s how difficult these are to crack. Check our favorite hard riddles of 2020 below.

1. What begins with T, ends with T, and has T in it? A teapot.

2. What English word retains the same pronunciation, even after you take away four of its five letters? Queue. 3. When you need me, you throw me away. When you don’t need me, you bring me back. What am I? An anchor. 4. You do not want me when you don’t have me, but when you have me you don’t want to lose me. What am I? A lawsuit. 5. 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? Heroine. 6. What do you get if you add two blackberries and five apples? A house full of gadgets. 7. What always ends everything? The letter “G” 8. I am an odd number. Take away a letter and I become even. What number am I? Seven. 9. Walk on the living, they don’t even mumble. Walk on the dead, they mutter and grumble. What are they? Leaves. 10. The more you have of it, the less you see. What is it? Darkness. 11. Can you name three consecutive days without using Sunday, Wednesday and Friday? Yesterday, today, and tomorrow. 12. If a red house is made of red bricks, and a yellow house is made of yellow bricks, what is a greenhouse made of? Glass, all greenhouses are made of glass. 13. What is next in this sequence: JFMAMJJASON? The letter “D.” The sequence contains the first letter of each month. 14. Which of the following words don’t belong in the group and why: CORSET, COSTER, SECTOR, ESCORT, COURTS? Courts. All of the others are anagrams of each other. 15. A man and his boss have the same parents, but are not siblings. How is this possible? He is self-employed. 16. What has four fingers and thumb, but it is not living? A glove. 17. What is light as a feather but even the strongest man in the world can’t hold it for that long? Breath. 18. What has a heart that doesn’t beat? An artichoke. 19. What can’t be used unless broken? Eggs. 20. Where do cows go for their holidays? Moo York. 21. What am I when today comes before yesterday? A dictionary. 22. What has golden hair and cleans up after you? A broom. 23. What moves without seeing and cries without eyes? A cloud. 24. What comes down but never goes up? Rain. 25. Round like an apple, deep like a cup, yet all the king’s horses can not pull it up. What is it? A well. 26. What question can you never answer yes to? Are you asleep yet? 27. What makes you young? Adding the letters “ng”. 28. I come from a mine and get surrounded by wood always. Everyone uses me. What am I? Pencil lead. 29. What can fill an entire room without taking up any space? Light. 30. What has one head, four legs, and one foot? A bed. 31. What’s made of water but will die if you put it in water? An ice cube. 32. I only lie down once – when I die. What am I? A tree. 33. I have four keys, but no locks. I have a space, but no room. You can enter, but can’t go inside. What am I? A keyboard. 34. What did the chewing gum say to the shoe? I’m stuck on you. 35. What can never be put in a saucepan? Its lid. 36. Give me food, and I will live. Give me water, and I will die. What am I? Fire. 37. What’s full of holes but can hold a lot of water? A sponge. 38. Not my sister nor my brother but still the child of my mother and father. Who am I? Myself. 39. What is always in front of you but can’t be seen? The future. 40. Every time you lose something, you always find it in the very last place you would look. Why is this? It is the last place you would look because once you find it there is no need to keep looking. 41. You bought me for dinner but never eat me. What am I? Cutlery. 42. What can be measured, but not seen? Time. 43. How many letters are in the alphabet? There are eleven letters in “the alphabet.” 44. What can an elephant make that no other animal can make? A baby elephant. 45. I can be written, I can be spoken, I can be exposed, I can be broken. What am I? News. 46. Smell me, buy me, and deliver me. I won’t change. What am I? Scent, cent and sent. 47. How do football players stay cool during a game? They stand next to the fans. 48. What type of dress can never be worn? Address. 49. What breaks on the water, but never on land? A wave. 50. What stays where it goes off? An alarm clock. 51. My rings are not of gold, but I get more as I get old. What am I? A tree. 52. What is at the end of a rainbow? The letter W. 53. The more you take, the more you leave behind. What are they? Footsteps. 54. What has ten letters and starts with gas? An automobile. 55. How many seconds are there in a year? 12 – January 2nd, February 2nd, March 2nd, April 2nd… 56. As a stone inside a tree, I’ll help your words outlive thee. But if you push me as I stand, the more I move the less I am. What am I? A pencil. 57. What’s black when you get it, red when you use it, and white when you’re all through with it? Charcoal. 58. You use a knife to behead me, yet you weep over me on my death. What am I? An onion. 59. What bird can lift the most? A crane. 60. I occur twice in eternity, and I’m always within sight. What am I? 61. What can you hold in your right hand but never in your left hand? Your left hand. 62. What can you fill with empty hands? Gloves. 63. What is stronger than steel but is afraid of the sun? Ice. 64. No sooner spoken than broken. What is it? Silence. 65. Forwards I am heavy, backwards I am not. What am I? Ton. 66. What has 12 faces and 42 eyes? A pair of dice. 67. How do you make the number one disappear? Add the letter G and it’s “gone”. 68. How many bricks does it take to complete a building mades of bricks? One brick – “complete a building.” 69. What has a neck but no head? A bottle. 70. How can you burn an apple, blueberry, rose and pumpkin without leaving any ashes but retaining the smell of it? Lighting scented candles. 71. What five-letter word becomes shorter when you add two letters to it? Shorter. (Short + ‘er’) 72. Where there is light is the only place I can live. Yet if light shines on me I die. What am I? A shadow. 73. What tastes better than it smells? Your tongue. 74. What can go through a glass without breaking it? Light. 75. What flies when it’s born, lies when it’s alive, and runs when it’s dead? A snowflake. 76. What can run, but not walk? Water. 77. What begins but has no end and is the ending of all that begins? Death. 78. What English word has three consecutive double letters? Bookkeeper. 79. What is seen in the middle of March and April that can’t be seen at the beginning or end of either month? The letter “R”. 80. What time starts and stops with “N”? Noon. 81. What word begins and ends with an E but only has one letter? Envelope. 82. Where can you find cities, towns, shops, and streets but no people? A map. 83. What do you bury when it’s alive and dig up when it’s dead? A plant. 84. What spends all the time on the floor but never gets dirty? Your shadow. 85. What is so fragile that saying its name breaks it? Silence. 86. What has hands but can’t clap? A clock. 87. What has branches and leaves, but has no bark? A library. 88. What kind of tree can you carry in your hand? A palm tree. 89. What can you never get rid of when you actually lose it? Your temper. 90. What has one eye but can’t see? A needle. 91. What can you keep after giving it to someone? Your word. 92. Why is an island like the letter T? Because it is in the middle of water. 93. How do you know carrots are good for your eyes? You never see rabbits wearing glasses. 94. What can you make that you can’t see? Noise. 95. What connects two people, but touches only one? A wedding ring. 96. What falls, but never breaks? What breaks, but never falls? Day and Night. 97. Who has married many women but was never married? A priest. 98. What has a head and a tail but no body? A coin. 99. If a brother, his sister, and their dog weren’t under an umbrella, why didn’t they get wet? It wasn’t raining. 100. What has teeth, but can’t eat? A comb.