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6 Memorable Riddle Scenes From Pop Culture

Riddles have been around for millennia, dating back to the oldest preserved example from the Sumerians. Even the term “riddle” itself hasn’t changed much from its Old English roots. In short, it still roughly revolves around the meaning of interpretation or understanding. That said, riddles have made their way into modern mediums. Some of the most memorable examples are those in movies and books.

Written by

Adam Johnston

Give me a bottle of bourbon and half a chicken, and I’ll conquer the world! My job is to make sure that everyone else does their job, which has to be the easiest job in the world considering the brilliant, hard-working people we have in our Flock. My ultimate goal is to run a company that people are proud to work for. I’m an avid statesman, adventurer, Burner, Broadway aficionado, athlete, and I wear my Cole Haans as often as my cowboy boots. It’s a wonderful life.All Posts

Did you know

There are two types of riddles. An enigma is a metaphorically expressed riddle and a conundrum is a tricky problem usually including a pun in its question or answer.

Harry Potter and the Goblet of Fire

Avid fans of the Harry Potter books might be able to guess which riddle we are bringing up. In the fourth installment of the series, Harry’s last task in the Triwizard Tournament is to navigate a dangerous maze to reach the prized Triwizard Cup. Among the many obstacles in the maze, one is a sphinx with a riddle:

“First think of the person who lives in disguise,

Who deals in secrets and tells naught but lies.

Next, tell me what’s always the last thing to mend,

The middle of middle and end of the end?

And finally give me the sound often heard

During the search for a hard-to-find word.

Now string them together, and answer me this,

Which creature would you be unwilling to kiss?”

Through some fumbled thoughts and sounding it out, Harry fortunately figures out that the answer to this riddle is “a spider” and he is not eaten by the sphinx as a result. Although this bit didn’t make it into the movies, it remains a memorable part of the Harry Potter fandom.

The Hobbit

An even more memorable moment for fantasy fans alike is the famous riddle scene in The Hobbit. This time, the riddles are featured both in the book and movie adaption. On his journey to the Lonely Mountain, he encounters Gollum in the bowels of the Misty Mountains. Before Gollum can kill him, Bilbo smartly challenges the Smeagol side of the creature to a battle of wits. Gollum agrees and concedes to let Bilbo go if Bilbo beats him and if not, Gollum will eat him. The harrowing confrontation goes on for a solid 9 riddles.

While it would take too long to go over all of the riddles asked, we decided to pick the one we liked best. This is one that Bilbo asks Gollum:

“An eye in a blue face

Saw an eye in a green face.

“That eye is like to this eye”

Said the first eye,

“but in low place

Not in high place.”

Gollum, who has spent too long in his cave, struggles to call upon his memories from the outside for this answer, which is “sun on the daisies”.

As you may know, the scene devolved into the famous final moment of trickery, in which Bilbo struggles to come up with another riddle and accidentally asks “What have I got in my pocket?”

Although lengthy, this scene is an integral part of The Hobbit and subsequent The Lord of the Rings saga and had characters and audience alike scratching their heads.

Monty Python and the Holy Grail

Fans of camp will note that the “riddles” in Monty Python and the Holy Grail are not so much riddles as satirical representations of them. Given that they are playing off the famous trope of answering three riddles to pass an obstacle, we decided to include it in this list.

As Sir Lancelot and his crew approach the Bridge of Death, the Bridgekeeper states that they must answer three questions in order to cross. Hilariously, none of the questions are actually riddles and make no sense. Each of the men address the Bridgkeeper in a manner similar to the following:

BRIDGEKEEPER: What… is your name?


LANCELOT: My name is ‘Sir Lancelot of Camelot’.


BRIDGEKEEPER: What… is your quest?


LANCELOT: To seek the Holy Grail.


BRIDGEKEEPER: What… is your favorite color?




BRIDGEKEEPER: Right. Off you go.

As the other men step up for their turn, it’s revealed that the Bridgekeeper doesn’t even know the answers to his own questions. The brilliance of this scene lies in the satirical take on people’s inability to answer difficult questions (such as “What… is the air-speed velocity of an unladen swallow?”), as well as simple ones. 

Batman Forever

Long-time Batman fans might recognize this one. In the third film of the initial Batman series, Jim Carrey’s character, The Riddler, leaves behind several riddles for Batman to solve. What’s interesting about these riddles is that they are enigmas and each has a number that correlates to a letter in the alphabet, which will reveal to Batman where the kidnapped Dr. Meridian is being kept. 

Out of the four riddles that The Riddler leaves for Batman, the one we liked best is: 

“We’re five little items of an everyday sort; you’ll find us all in ‘a tennis court’.”

Eventually, Batman finds The Riddler and faces his hardest riddle yet, one that is highly metaphysical: “Can Bruce Wayne and Batman ever truly co-exist?” Moody, huh? 

Although Carrey’s portrayal of The Riddler was entertaining to behold, we hope to see the character return in one of the certainly upcoming Batman films.

National Treasure

Whether you’re a true Nicolas Cage fan or simply a fan of his proclivity to be a meme, it’s likely that you’ve seen the 2004 hit National Treasure. The film is full of clues, codes, and riddles leading Cage’s character, Ben, to a bountiful treasure. 

Early on in the film comes the first riddle, which is one that will play an underlying role throughout the rest of the film. 

“The legend writ, the stain affected.

The key in Silence undetected.

Fifty-five in iron pen,

Mr. Matlock can’t offend.”

Being the skilled code-breaker that he is, Ben quickly deduces that the answer is the Declaration of Independence. From here, the race to the treasure begins and has us all questioning how much we really know about America’s history.

Alice in Wonderland

Perhaps one of the most infamous riddles of all time comes from the classic Alice in Wonderland. Upon meeting the Mad Hatter at the Mad Tea Party, the hatter asks Alice the following riddle: 

“Why is a raven like a writing desk?”

Some state the answer as being “Poe wrote both”, however, Lewis Caroll later said “Because it can produce a few notes, tho they are very flat; and it is never put with the wrong end in front!”, although it’s largely not taken as the true answer since he admitted to not having one and this statement came after much pestering from readers. In fact, the original “answer” was to be “never” spelled like “nevar”, which is “raven” spelled backwards. However, an editor took it as a mistake and omitted it before publication.

Will we ever truly know the answer to this one? Maybe not, but we’d love to hear your theories.

Riddles have proven themselves hardy against the test of time, finding new ways into modern mediums and making us scratch our heads. Although sometimes frustrating, we love the brain exercise riddles provide and the excitement of having them presented to us in new forms. With entire characters and integral scenes orbiting around their concept, it doesn’t seem that riddles are going anywhere anytime soon.