Posted by John Hayden on July 18, 2000
My understanding is that this phrase may have originated as a farming term, referring to how good a farmer's harvest was. For example: An average, or "fair" harvest would fill a silo about half way, or to the "middle." Hence, when someone would ask the farmer how his harvest went, he would reply "fair to middling", meaning ok, fair, average, etc. I'm afraid I don't have a time frame for this explanation. Does anyone have an alternate possibility of the origin of this phrase or a time frame for this explanation?