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The word 'canny' means shrewd, and the prefix un- is negative. So, it seems that 'uncanny' should mean something like dumb. Yet, it doesn't. According to Cambridge Dictionary, 'uncanny' actually means
strange or mysterious, often in a way that is slightly frightening.
Besides, when you search 'uncanny' in Youtube, lots of horror videos turn up.
Why doesn't 'uncanny' mean something like dumb? Are there other pairs of words like this?
There are some "unpaired" un- words, like "ungainly". This now means "clumsy/awkward in movement". This derives from an original word "gein", which meant "suitable for purpose, helpful, reliable". The base word "gein" has gone out of use in English, and the sense of "ungainly" has shifted, from "inconvenient, unfit for purpose" to its modern meaning. The shift in meaning was possible because it was an unpaired word.
A similar sense shift happened with uncanny. The word "canny" dropped out of English (as spoken in the South of England) and the unpaired word "uncanny" shifted in meaning. However the word "canny" was preserved in Scottish dialect, and then re-entered English from Scots. It is still much more common in Scottish English.
Another similar pair is "untoward" It is not an antonym of "toward". But means "unexpected and inappropriate or inconvenient."
I've thought of another one: Unwind, means "relax", and while we might say "I'm wound up", we don't use "wind" to mean become stressed.
...probably because it's obscure and complicated.
The root word here is "ken", which is obscure in English but common in German and has a similar meaning there. It's slightly difficult to define: the usual definition is "understanding", which is right but misleading. "Ken" is perhaps closest to familiarity; people and things you ken are people and things you have met and recognize. Compare also a "kenning," sort of a mini-riddle in Old Norse.
"Canny" is an adjective form of ken, and you correctly identify that it does double-duty:
The second meaning fell out of use, but its antonym stuck around as "un-canny". Sometime in the nineteenth century it picked up supernatural connotations as well, leaving us with the meaning it has today.
Ultimately, it's analogous to the difference between "knowing" and "unknown".
