In a conversation the other day, someone used the expression “it costs a pretty penny.” My father used to use it, but I haven’t heard it around for quite some time and wondered if it was one of those near-dead expressions. It’s not. I guess as Nat King Cole sang, I Don’t get around much anymore.
A PRETTY PENNY: A considerable sum of money; cost – ‘an arm and a leg.’ That fur coat must have cost a pretty penny.
Etymology: 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)
However, since the term ‘pretty penny’ didn’t appear in print until 1710 one may wonder why it took the better part of five centuries from the time the coins were minted for word of them to show up on the written page, and whether Henry’s coins were still in circulation, or were even thought much about, by the 18th century. But, as Wiz often points out words can hang around for hundreds of years – even thousands – in the spoken word before they ever make it into print! (<;)
The following quotes are from the Oxford English Dictionary and archived sources:
______________________<1710 “Why here may be a pretty Penny towards, if the Devil don't cross it.”—The Man’s Bewitch’d by S. Centlivre, i. i. page 3>
<1780 “. . .if these ar’n’t mock diamonds round it, it will bring a pretty penny.”—The Deaf Lover by F. Pilon, page 15>
<1860 “That watered-silk she had on cost a pretty penny.”—The Mill on the Floss by George Eliot, I. ii.i. page 256>
<1885 “Then the captain might still make a pretty penny on Amita.”—Maruja by Bret Harte, i>
<1915 “It must have cost you a pretty penny. It's lucky you can afford it.”—Of Human Bondage by Somerset Maugham, lxxiii, page 377>
<1955 (advertisement “You’d think that rolls with mouth-watering flavor and feather-light tenderness of MILLBROOK Chef Rolls would cost a pretty penny! But No! You buy them for no more than you pay for the ordinary kind!”–Galveston Daily News (Texas), 22 November, page 6> [[But are they whole-wheat and organic?]]
<1994 “Jean films the boy hanging from a skyscraper; Sami later gibes that, had he fallen, Jean could make a pretty penny selling the footage.”—Film Comments, January-February, page 75/3>
<2011 (article title) “Ugly Christmas Sweaters Turn A Pretty Penny”—NPR, 20 December>
Ken G – January 2, 2012 (penny foolish and pound wise)