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Mind-Boggling Riddles From Movies

Updated May 27, 2021 9.8k votes 2.3k voters 159.9k views16 items

List RulesVote up your favorite mind-boggling movie riddles.

Riddles are fun. Movies are fun. Movies with riddles in them? That's got to be double fun! People have been trying to stump each other with riddles since the days of ancient Babylon. Nearly every time and culture has had its share of brain teasers. Something about the challenge and mystery of a word problem makes people want to step up and solve them.

With their popularity, it's only natural that movies would incorporate riddles. Action, horror, mystery, and adventure films make use of the riddle's inherent frustrations. It's a truly tense situation when a character is trying to solve a problem before a clock ticks down and we the audience are trying the figure out the solution as well. These are some of our favorite conundrums pulled from the silver screen.

  • Photo: Labyrinth / Tri-Star Pictures

    In the classic film Labyrinth, Jennifer Connelly's character and the audience are frustrated by the riddle of the lying door guard.

     

    The 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?

     

    The 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.

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  • Photo: Inside Man / Universal Pictures

    In the Spike Lee film Inside Man, Clive Owen's and Denzel Washington's characters have a battle of words, including this puzzler.

     

    The 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?

     

    The Answer:

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

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  • Photo: National Treasure / Buena Vista Pictures

    In National Treasure, Nicolas Cage's character deciphers a series of clues to unravel a historic mystery. This is what sets it in motion.

     

    The Riddle:

    The legend writ, the stain affected. The key in Silence undetected. Fifty-five in iron pen, Mr. Matlock can’t offend.

     

    The Answer:

    The Declaration Of Independence

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  • Monty Python and the Holy Grail contains a classic riddle with an answer that truly doesn't matter.

    The Riddle:

    What is the airspeed velocity of an unladen swallow?

     

    The Answer...?

    African or European?

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