Definition: A mischievous/cheeky person, a ‘whippersnapper’.
William de la Pole (1396-1450), the Duke of Suffolk, was known by this nickname. The meaning of Jackanapes presumably describes his personality. He was the Lord of the Admiralty and was one of the first commoners – originally a merchant – to be admitted into the ranks of the nobility. This was seen as something of an impertinent thing to do in and of itself – thus further enhancing the name.
The name itself probably derives from ‘Jack of Naples’ – the term used by the English in the 15th century to describe a monkey. Monkeys at the time, when imported into England, came via the port of Naples.
Why This Word:
It is quite unusual to have a word that can be ascribed to originating with a known individual. The idea that William de la Pole’s nickname would enter the English language as a word in its own right is fascinating. Indeed, de la Pole himself entered English literature, being a major character in Shakespeare’s Henry VI parts 1 & 2.
How to use this word:
Despite its interesting history and link to a genuione person, Jackanapes is a difficult word to use in the 21st century. In short, it does not have the necessary sound for a modern-day swear word. We like our swear words to be short, which it is not, contain definitive consonants at the end, which it does not have, and to be somehow related to a sexual act – which, given the reference to a monkey, one can only hope it does not …
My advice – if you’re name is followed by ‘The Third’, you can use it. If you’re still only a ‘junior’, this one is not for you.