Wednesday's Random Slang-o-rama: A pretty penny

If something costs a pretty penny, you can bet that you'll be paying more than just one shiny copper coin.

So, why (and when) did a pretty penny come to mean a large sum of money? A regular Slang-o-rama reader asked me about this phrase, and as I'm always happy to jump in on special requests and see what I can find, let's hop to it.
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Hop!

The American Heritage Dictionary of Idioms by Christine Ammer provides the expected definition—"a considerable sum of money"—and dates it to early 1700s. The Phrase Finder gives us a little more background:

'A pretty penny' used to have the variants 'a fine penny', 'a fair penny' etc, but these have fallen by the wayside. All the forms of the expression came into the language in the 18th century and an early example is from a play by the popular playwright Susanna Centlivre, The Man's Bewitch'd, 1710: "Why here may be a pretty Penny towards, if the Devil don't cross it."

Intriguing, but I was hoping for an explanation as to why a "pretty" penny. Shiny or worn, a penny is worth the same, right? The Online Etymology Dictionary reminded me that, since the late 15th century, pretty has also been used to mean "not a few, considerable." Yes, I could see where that definition might (Dare I say it? Yes, I dare!) make sense(cents) in this context.

However, I think I will give the final word to the Wordwizard site, where this theory was posited:

The origin of this phrase is uncertain but it is often attributed to the special gold pennies, worth 20 silver pennies, that Henry III had coined in 1257. Since they were more valuable than the silver pennies, they became known as pretty pennies. (Picturesque Expressions by Urdang, American Heritage Dictionary, Facts on File Dictionary of Clichés)

So, there you go, inquiring reader. Pretty as in considerable or pretty as in gold? You choose! However, no matter how you look at it, if something costs a pretty penny, it'll probably also cost an arm and a leg. (More about that next week.)

More than one pretty penny in that pile...
Image by makingmilly from Pixabay

*Cents, because I cannot resist the possible pun...