The following is a modified excerpt from the book Useless Etymology: Offbeat Word Origins for Curious Minds.
The word “conundrum’ first appears in English in the late 16th century, supposedly at Oxford University, where it was used as an insult for an overly pedantic or studious person, which suggests it might be mock-Latin, perhaps poking fun at someone a bit too invested in their Latin studies.
In other words, conundrum doesn’t mean much of anything etymologically—it’s more or less Latin gibberish—but it originally served the purpose of the word “nerd” (an insult that also originated on college campuses, but not until the 20th century, before which it also appeared as the apparently unrelated name of a fanciful creature in Dr. Seuss’ If I Ran the Zoo).
In the next century or so, the meaning of “conundrum” diversified. It could mean…
- A whim, or a fanciful thought or phrase: One might be said to “have strange conundrums in one’s head.”
- A punny quip or a stupid joke: Samuel Johnson’s dictionary defines it as “a low jest; a quibble; a mean conceit: a cant word.”
The spelling of this word also went off the rails—though, since it lacks a firm origin, who’s to say it really had an approximation of a correct spelling in the first place?
Variations included “conimbrums,” “qunnundrum,” “conuncrums,” “cunnunders,” and “quadundrums.” Some of these appear to be trying to connect or conflate it with “quandary,” which is also pseudo-Latin, possibly inspired by the Latin quando, meaning “when?” or “at what time.”
My personal favorite variation of “conundrum” is quinonbroms, mostly because of the context in which it appears.
In 1770, historian and political writer James Howell assembled a work that he called “Lexicon tetraglotton,” ostensibly a English-French-Italian-Spanish dictionary, but more a heavily editorialized collection of words and phrases in these languages across several disciplines. In it, he wrote:
You will judge perhaps, that the Author hath some strange freaks, or quinombroms in his noddle.
And indeed, that might be your judgment of his book, but given that you’ve made it this far into this this post, I think you and I would both be hypocrites if we were to cast stones at people with quinonbroms in their noddles.
In the late 18th and early 19th centuries, “conundrum” arrived at today’s meaning: It went from a punny play on words or a whimsical thought to a riddle (that might include a pun or word play), and from there was extended to a word for a generally puzzling or difficult, or even unanswerable question or situation.
Dean Rivers’ 1903 Conundrums, Riddles and Puzzles is stuffed with both punny and philosophical riddle-like conundrums, beginning with the following, which nods to the idea that “true” conundrums cannot be answered or solved:
Q: Why is life the greatest of all conundrums?
A: Because we must all give it up.
A few more from this work on the less philosophical side:
Q: Who is the greatest chicken-killer spoken of in Shakespeare?
A: Macbeth, because he did murder most foul (fowl).Q: Why do we generally dub a city her or she?
A: Because about a city there is so much bustle and because she has outskirts.Q: Why is a professional thief very comfortable?
A: Because he usually takes things so easy.
Useless Etymology 