It's a rather odd thing but, when I was in Dumfries a year or two ago, I was told - as part of an otherwise forgettable conversation in a pub - that the Jock Stewart of the song was reputed to be a notable singer from Eskdale. Indeed, I had even forgotten this until this thread reminded me.

I'd always been puzzled a bit as to why an apparently Scottish song used the Northern English meaning of the word "canny", so a home for it in the border country (where the meaning of a word might be less unequivocal) seemed to me at least to make some sense.

This afternoon, being bored, I did an internet search on JOCK STEWART ESKDALE using Vivisimo. I found a number of references to Samuel Smiles Life of Thomas Telford.

Searching for Stewart in the text, I came across the following quote (following Telford's visit to a concert by Mrs. Jordan).

"It was all very fine," he said, "I have no doubt; but I would not give a song of Jock Stewart *[10] for the whole of them.

In a footnote, it says that Jock Stewart was

An Eskdale crony. His son, Colonel Josias Stewart, rose to eminence in the East India Company's service, having been for many years Resident at Gwalior and Indore.

Nothing positive, and I wouldn't suggest that this provides any real evidence, but it seems that the notable Jock Stewart from Eskdale did at least exist.

:-)