Five Fictional Riddles That Can’t Be Solved

The literary, cinematic and funny-paper canon is full of riddles because they’re as fun for the audience as they are dire for whichever hero must solve them to obtain the One Ring, whatever the hell a sorcerer’s stone is, etc. But just like some rules are meant to be broken, not all riddles are meant to be solved. We’re gonna go finish writing our country song, but in the meantime, don’t bother with…

5 Alice’s Adventures in Wonderland

Just a few pages after the Mad Hatter asks Alice, “Why is a raven like a writing desk?” in the rant against modern math most beloved by hippies, the answer becomes clear: He doesn’t know. Alice only mistook it for a riddle. It’s just the ravings of a guy for whom cognitive fog is one of only two defining traits. Lewis Carroll couldn’t have made it more obvious if he’d written the outburst into an argument about semantics — oh, wait, he did.

Still, that didn’t — and hasn’t — stopped readers from trying to come up with an answer. The most popular is probably “Poe wrote on both,” but they range in elegance from “Both have quills dipped in ink” to “Both have flaps.” Thirty years after Alice’s Adventures were published, Carroll added an explanation in a foreword to new editions, ostensibly to put the matter to rest but, in true Carroll fashion, only obscuring it further: “Because it can produce a few notes, though they are very flat; and it is nevar (sic) put with the wrong end in front!”

Are you people happy? You made Lewis Carroll pun.

4 Life Is Beautiful

One of the characters in the 1997 Oscar-winning Holocaust comedy (you had to be there) Life Is Beautiful, Dr. Lessing, is a German officer and frequent customer of protagonist and Italian Jew Guido’s uncle’s restaurant. He’s also obsessed with riddles, because hey, we all contain multitudes.

Toward the end of the movie, Lessing begs Guido for help with a riddle, translated to English, “Fat, fat, ugly, ugly / All yellow / If you ask me where I am, I say ‘quack, quack, quack’ / Walking along, I say ‘poo poo.’” Sound like nonsense? It is. Writer/director/star Robert Benigni said it’s meant to illustrate the absurdity of war. Lessing is sure it must be a duck, but it drives him crazy and he never figures it out, because, like, that’s what war does, man.

That explanation hasn’t satisfied all viewers, though, some of whom believe it’s describing an anti-Semitic stereotype of Jews. They also insist it must mean something that the Italian word for “quack” also means “here,” but it’s unclear what that has to do with Judaism. Even moreso the poo poo.

3 Twelfth Night

If you don’t remember your Shakespeare or at least your Shakespeare in Love, several characters surrounding Twelfth Night’s Olivia decide to catfish her steward, Marvolio, into thinking she’s into him, basically just because he’s an asshole and it’s funny. They plant a letter for him to find that never actually addresses him or identifies the writer as Olivia but contains hints meant to trick him into thinking it is, including the cryptic codename M.O.A.I. As expected, Marvolio convinces himself it refers to him because all those letters are in his name and he’s dumb as a frilled collar.

Clearly, M.O.A.I. is a joke at Marvolio’s expense, but Shakespeare apparently wanted us to fill in our own blanks (Marvolio Ought to Anally Insert?) because it’s never explained what these letters really stand for. It’s also plagued Shakespearean scholars for centuries. Some have suggested that it’s an anagram for “I Am O,” meaning Olivia; a reference to the pamphlet war (yep) between Elizabethan writers Thomas Nashe and Gabriel Harvey; a biblical reference; or a “visual pun on the hangman’s noose.”

Our theory is that Shakespeare wrote fart jokes and never intended anyone to think this hard.

2 The Hitchhiker’s Guide to the Galaxy

Every nerd’s favorite number is 42, supposedly “the answer to the ultimate question of life, the universe, and everything” calculated by the supercomputer Deep Thought in The Hitchhiker’s Guide to the Galaxy. The joke is that the scientists who built the computer didn’t have a precise enough question, yielding a meaningless answer, and author Douglas Adams was very clear on that.

“It had to be a number, an ordinary, smallish number, and I chose that one. Binary representations, base thirteen, Tibetan monks are all complete nonsense,” he said, referring to various theories. “I sat at my desk, stared into the garden and thought ‘42 will do.’”

You could argue that it’s a symbol of the arbitrary nature of life, but Adams would have walked away before you finished.

1 Monty Python and the Holy Grail

There isn’t a single serious syllable in Monty Python’s 1975 send-up of the Knights of the Round Table, so naturally, when Arthur and the gang come upon a bridge troll who makes them answer riddles to cross the bridge, they aren’t really riddles, just trivia and personal questions. One guy gets yeeted into Eternal Peril for misremembering his own favorite color. It’s a good bit.

When it’s Arthur’s turn, the troll asks him, “What is the airspeed velocity of an unladen swallow?” and it just so happens Arthur witnessed that exact debate earlier in the movie, so he asks, “An African or European swallow?” tricking the troll, who didn’t have one in mind, into plunging to his own presumed grisly death. This has given comedy nerds a handy call and response by which to identify each other but also an actual riddle: What is the airspeed velocity of an unladen swallow?

The real joke: It’s a trick. There’s no such thing as “airspeed velocity.” Sure, you could calculate the airspeed or the velocity of a swallow of any nationality. Or you could just watch Monty Python and the Holy Grail again. Heh. Swallow.