Unless you are fond of Shakespeare, this word will not often crop up in your personal dictionary. Pity, as I say about older words that I love. It has fallen out of favor long ago, but what sort of ape are we talking about?
A tame one, apparently. But still an ape, which leads to the Shakespearean sense of a person who is impenitent, foolish, or who does things like a trained ape, playing tricks that amuse us. Consider Doctor Caius, a Frenchman of short temper and Monty-Pythonian insults in Merry Wives of Windsor:
I will teach a scurvy jack-a-nape priest to meddle or make.
Years ago, I saw a wonderfully dreadful production of the play locally. I won’t say where or when, but it was so bad that it was great. I did learn the word at least. Caius is, finally, the biggest jackanapes of them all.
Considering the history of the term opens a veritable etymological barrel of monkeys. The OED gives more variant spellings than I’ve seen before, reaching as far back as Middle English: iac nape, iac napes, jacknape, shacknapes, and many more. So to get to the bottom of all this monkey business, it comes down to a proper name “apparently coined as a generic proper name for an ape or a person likened to an ape.” I suppose a modern analog would be a “Negative Nelly” or “Simple Simon.”
We don’t call a person playing tricks or an unruly child a Jackanapes any longer. Again, pity. Check the OED entry for a lot more, even a botanical meaning, for this peculiar, obsolete word you will still find in literary works from a certain era.
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Creative-Commons image of Dr. Caius from the collection of The National Galleries of Scotland.