Can You Solve This Old-Timey Riddle? #34

In 1511, the English printer and publisher Wynkyn de Worde (a contemporary of diplomat and writer William Caxton) published a short book of riddles called The Demaundes Joyous. The book contained only a few pages and barely 50 question-and-answer style riddles (or “demands”) in total, but it has assured itself a place in history as the first book of riddles ever printed in the English language.

Unfortunately, many of the Demaundes in the book tend to fall into one of three increasingly bizarre categories. Some are simple trivia questions, intended to test the reader’s knowledge of the Bible. Next, the vast majority of the book consists of back-and-forth lateral-thinking questions that are either so tenuous or so of their time that they’re all but unsolvable today. (“What man is he that getteth his living backward?” asks one puzzle, the answer being “a rope maker”—because ropemakers would apparently walk backward while twisting together the strands of a rope so it didn’t become tangled.) Most bizarre of all are the final set of puzzles, which could be labeled as little more than toilet humor: “What beast is it that hath her tail between her eyes?” asks one riddle, to which the answer is, “A cat, when she licks her arse.”

The 37th puzzle in The Demaundes Joyous, however, is a good old-fashioned brainteaser that has remained in popular circulation in puzzle and riddle collections ever since it was published. In fact, you might have heard this one before—but if you haven’t, here’s a clue: The answer is a human-made structure. Can you work it out?

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