Not to be confused with fun.
Dear Word Detective: My dad, who hails from the coast of Scotland, is a great source of idioms I rarely (if ever) hear from friends and co-workers. Unfortunately, like most people, he uses expressions with no idea where they actually came from and has only a passing understanding of what they mean. One of these pet expressions is “a devil of a time” which he uses to describe unpleasant tasks that must be done and put him in a bad mood such as “a devil of a time” fixing the roof or unclogging the toilet. I’m just guessing here, but by any chance does this phrase owe its origins to the ugly business of re-caulking wooden-hulled ships while at sea? I seem to recall “the devil” being a term for the planking around the waterline of the hull. — Steve.
Your father’s understanding of “a devil of a time” is actually right on the mark, and, as someone who has unclogged a lot of toilets, I admire his restraint. I usually come up with far less printable ways to describe such tasks. My personal least-favorite chore is dragging fifty-pound sacks of salt into the cellar and dumping them into our so-called water softener every month. I hate this ritual so much that I actually feel a rush of annoyance when I see people lifting weights on TV. Come to my house, bucko, and I’ll waive the gym fees.
“A devil of a time” is actually a very old and very widespread expression, as well known in the US as it apparently is in Scotland. The construction “a devil of a,” meaning “an extremely irritating or difficult example of something” (“a devil of a day,” “a devil of a problem,” etc.) dates back at least to the mid-18th century. The logic of the phrase is a comparison of the thing in question to Satan or his devilish ways, and was originally taken as a serious condemnation, i.e., a “devil of a man” was a truly bad character. Today the phrase has softened to mean simply “unpleasant, annoying or difficult” (“I had a devil of a time programming my iPod”).
The nautical use of “devil” to mean a seam in a ship’s hull difficult to reach while caulking is often cited when explaining the phrase “the devil to pay” meaning “in a difficult situation.” “Pay” does indeed have the meaning of “seal with pitch” (from the Old French “peier,” pitch or tar). But no one has ever been able to establish that any particular seam on a wooden ship was called “the devil.” Furthermore, the supposed “full” form of the phrase, “the devil to pay and no pitch hot,” did not appear until the mid-19th century, roughly four centuries after “the devil to pay” was in use by landlubbers. It’s pretty clear that “the devil to pay” originally simply referred to the classic Faustian bargain with Satan and its unpleasant consequences. The story about “the devil to pay” springing from an unpleasant caulking job aboard ship was a later invention based on the coincidence of “pay” meaning “caulk” and “pay” meaning “satisfy a debt.”