To choose between two, in some way equally problematic, situations.
Hmmm. To be face down Old Nick himself, evil incarnate, on one hand, or, on the other hand, the endless danger of the fathomless, roiling sea… sounds harrowing. But actually the choices represented by this idiom are pretty mild, and the phrase is usually used in the spirit of fun or for dramatic effect.
For example: “What will it be tonight, Chinese or Italian? Chocolate or vanilla ice cream? I can’t decide. I feel like I’m standing between the devil and the deep blue sea.”
There seems to be a dispute as to the origin of “between the devil and the deep sea,” the form in which this phrase first appeared in 1637.
According to the good people at the The Phrase Finder, one group of wordsmiths holds to the theory that the “devil” in this idiom refers to an old nautical term that describes the seam between a wooden ship’s deck planking and the top planks of the ship’s side.
Since this seam would have to be regularly caulked to keep the ship watertight, a sailor would be held aloft on ropes to daub the “devil.” To accidentally fall one way was to plunge in an unforgiving sea, to fall the other way would mean a dangerous landing on a hard wood deck. Thus two possibly bad outcomes, with a crew member suspended in the middle of them.
But then again, as noted, other experts see a conflict among the dates of references to “between the devil and the deep sea,” and instead posit that the phrase arose just through common belief – that on the outside of the ship was the rancorous ocean, and on the other, not safety, but just one more place where Satan, the tricky devil, would hide to cause harm.
While the expression has been around for a long time, it was in 1931 that the musical team of Ted Koehler and Harold Arlen wrote the love ballad Between the Devil and the Deep Blue Sea, adding the word “blue” to the already common phrase. The popularity of the song ensured the idiom’s use for more generations to come. The song was first recorded by Cab Calloway, of Harlem’s Cotton Club fame, and has since been covered by Frank Sinatra, Ella Fitzgerald, and Thelonious Monk, as well as by many other artists.
My favorite rendition of Between the Devil and the Deep Blue Sea is by the late George Harrison of the Beatles, who included it on his last album, Brainwashed.