Fair to middling
Slightly above average.
'Fair to middling' comes to the party with two friends, fair to middlin' and fair to midland. Both of these gatecrashers derive from the original phrase, but in different ways. Fair to middlin' is just a colloquial version written in the way that the expression is often spoken, in mid-west America at least, which, as we will see, is where the expression originated.
'It's middling' - not 'midland'.
Fair to midland is an odder fish and comes from the mispronunciation of 'middling' as 'midland'. The question is, why would anyone do that? It could be just a simple mistake, although that seems unlikely as 'fair to midland' doesn't really mean anything. More likely is that it was the result of a deliberate jokey mispronunciation, along the lines of san fairy Ann, taking the Miguel etc. This could have originated in the English Midlands. It is widely used there and the English are inveterate 'accidentally on purpose' mispronouncers - Cockney Rhyming Slang is an entire dialect built along those lines. In the case of 'fair to midland', the origin is more likely to be the USA, specifically Texas, the reference being to that state's city of Midland. The earliest printed citation of 'fair to midland' that I can find comes from The New York Times, May 1935:
Dr. William Tweddell, who is what might be called a fair-to-Midland golfer...
The current usage of the expression is predominantly American and has been boosted by the popularity of the US hard rock band that has adopted it as its name.
As to the original version of the phrase 'fair to middling', that is also of American origin. 'Middling' was and is a term used by farmers to describe the quality of farm produce, especially sheep. There were several loosely defined grades of produce: 'good', 'fair, 'middling', 'ordinary' and 'poor'.
'Middling' is an old Scots word and has been in use since at least the 15th century with the same meaning as now, that is, 'of medium or moderate size, strength, quality'. Around 1450, the Marquis of Bute wrote the Dictionary of the Older Scottish Tongue, which includes what appears to be the earliest example of 'middling' in print:
'The ynch sulde be with the thoum off midling mane nother our mikil nor our litil bot be tuyx the twa'.
I interpret that Old Scots text as meaning 'The inch should be measured with the thumb near the middle, neither at the largest point nor the smallest but between the two' but, if there are any old Scots out there who know better, I would be happy to be enlightened.
'Fair' was used in the UK from the 18th century onward to describe farm produce. An example of that usage is found in John Mortimer's farming handbook The Whole Art of Husbandry, 1707:
As you gather your Fruit, separate the fairest and biggest from the middling.
These farming terms travelled to America with the early Scottish and English settlers. Like sailors who, when they needed finer designations of direction than North, East South and West, came up with South-west, North-east etc., farmers needed a name for 'not quite fair but better than average' and they opted for 'fair to middling'. The earliest uses of the expression all come from the USA, as does this example from an 1829 edition of John Stuart Skinner's farming journal The American Farmer:
Two or three lots of good wethers [castrated rams] brought from $2.50 a 3 per head, and a few lots of fair to middling, $1.50 a 2.
Farmers didn't stop there and came up with other intermediate grades, like 'good fair'. Needing finer and finer classifications of quality, they again followed the sailors' lead and copied their 'North-north-east' style. In 1873, Beeton's Dictionary of Commerce described a delivery of cotton as:
Good fair to good saw-ginned Surat cotton.