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I recently read, can't remember where, of someone who didn't know diddle and squat.
Hmmn, that's a new one on me. I grew up hearing of those who didn't know diddley-squat, or sometimes they knew diddly or didn't know squat. I don't know why they DID know diddley, but didn't know the others.
Dictionary.com defines diddley-squat as doodly-squat, and for origin says it's probably a variant of diddlyshit (no hyphen). They define diddlyshit as meaning 1 of diddly, which us "a thing of little or no value; naught:" (meaning 2 means "a flaw or malfunction." The origin of diddly is an Americanism, probably earlier than 1960-1965, and it's perhaps a euphemistic shortening of diddlyshit.
I would venture that diddley-squat was well-established in the 1950s. Now, it's obvious that if you need to take a dump and you're an agricultural worker, you don't walk a half a mile up to an outhouse, you just drop trou and squat, and then cover over the fecal mass. And to diddle is to engage in coitus with someone, or by extension, to screw around with a gizmo trying to get it to work. Would diddley-squat originally literally mean what we now call santorum?
Bo Diddley was born Ellas Otha Bates and renamed Ellas McDaniel as a child. I can't remember what the product was that talked about someone who knew a couple of celebrated "Bo"s, but didn't know Diddley, showing a clip[ of Bo Diddley. The origin of his name is unclear; he says other musicians gave him the nickname as an insult, and that it was a singer his mother had known. Maybe they were calling him evidence of his father bring cuckolded? I note that "Jelly Roll" as in "Jelly Roll Morton is either an endearing reference to the woman's organ which Robin Williams thought worthy of veneration, or an insult referring to the monthly jelly-like discharges from a syphilitic whore.
I haven't had much success coming up with anything on the ngrams viewer. I think the various spellings of diddley, and the presence or absence of the hyphen, are factors that reduce frequency, and the great numbers of euphemisms for cunt, none of which are particularly acceptable in polite company, reduce frequency still more. These days, or course, I imagine most people would not object if the heard a preacher say "diddly-squat" from the pulpit. To them, it's quaint and colorful and in no way offensive. And of course, you can mention Jelly Roll Morton and Bo Diddley on television without blushing.
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