Our Favorite Mind-Boggling Riddles That We Finally Solved In 2021

List Rules
Vote up your favorite mind-boggling riddles.

Who doesn't love a good riddle? Probably people who get easily frustrated. But besides them, most of us enjoy being enticed by the clever wordplay and tricky construction of a little mind-bender every now and then.

Riddles can take many forms and come to us in a variety of ways. We've seen mind-bogglers launched our way in movies, had head-scratchers lobbed at us from television, and even dug up a few cleverly quixotic quips from both the medieval and Victorian eras. These are our favorite riddles that we finally solved in 2021.


  • Riddle:

    There are two doors. One leads to the castle; the other, to certain death. You may ask one question, to one guard, to help you decide which door is the correct one. One guard always lies, and one always tells the truth. How do you choose?

     

    Answer:

    Ask either guard which door the other guard would say leads out. To stay alive, you must walk through the opposite door you’ve been told to use.

  • This Math-Heavy Riddle From 'Brooklyn Nine-Nine'
    Photo: Fox / NBC

    Riddle:

    There are 12 men on an island. Eleven weigh exactly the same amount, but one is slightly lighter or heavier. You must figure out which. The island has no scales, but there is a seesaw. You can use it only three times.

     

    Answer:

    Use the seesaw to weigh islanders 1-4 against 5-8. This could have three possible outcomes:

    1-4 are the same weight as 5-8.

    1-4 are heavier than 5-8.

    1-4 are lighter that 5-8.

    If 1-4 are heavier,you know one of the islanders in 1-4 is heavier, or that one of the islanders in 5-8 is lighter. Also, you would know islanders 9-12 are the standard weight, neither heavier nor lighter.

    Now weigh 1, 2, and 5 against 3, 6, and 9. If the scale tips in the same direction as before, you know either 1 or 2 is heavier or 6 is lighter. Now weigh 1 against 2. Whichever side goes down is heavier. If neither goes down, 6 is the lighter.

    If on the second weighing, the seesaw tips in the other direction, then either 3 is heavier or 5 is lighter. Weigh 5 against 12. If it goes up, 5 is lighter; if not, 3 is heavier. If the balance of the second weighing is even, you know from the first weighing that either 4 was heavier or 7 or 8 was lighter. Now weigh 7 against 8. If one side goes up, that is the heavier one; if they are even, 4 is the heavier one.

  • Riddle:

    What's weightless, can be seen by the naked eye, and when put in a barrel makes it lighter?

     

    Answer:

    A hole.

  • Some Old-School Riddler Riddles From 'Batman'
    Photo: ABC

    Riddle:

    How many sides has a circle?

     

    Answer:

    Two, inside and outside.

     

    Riddle:

    Which president wears the largest hat?

     

    Answer:

    The one with the biggest head.

     

    Riddle:

    What is it that no man wants, but no man wants to lose?

     

    Answer:

    A lawsuit.

     

    Riddle:

    What is always on its way here but never arrives?

     

    Answer:

    Tomorrow.

  • A Riddler Riddle From 'Batman: The Animated Series'
    Photo: Fox

    Riddle:

    I have billions of eyes, yet I live in darkness; I have millions of ears, yet only four lobes; I have no muscle, yet I rule two hemispheres. What am I?

     

    Answer:

    A human brain, which has billions of optic and auditory nerves, four lobes, and two hemispheres.

  • Riddle:

    What weighs more: all the trains that pass through Grand Central Station in a day, or all the trees cut down in a year to print US currency?

     

    Answer:

    They weigh the same - nothing. US currency is not printed on paper from trees, and trains go through Grand Central Terminal (not station).