Here is a book written in 1902 that traces the origina of the phrase:

“Slang and Its Analogues Past and Present: A Dictionary, Historical and Comparative, of the Heterodox Speech of All Classes of Society for More Than Three Hundred Years” by John Stephen Farmer and William Ernest Henley.

Simply type in “pretty penny” in the right hand search column.

Pretty Penny

interestingly in Shakespeare’s Antony and Cleopatra of 1606, interior the speech on the tip of Act One wherein Cleopatra is regretting her youthful dalliances with Julius Caesar: “My salad days, while i grow to be eco-friendly in judgment”. So the word got here to recommend “a era of youthful inexperience or indiscretion”, however it in basic terms became common from the middle of the 19th century on. The link right here is eco-friendly, which had already had a which capacity for a pair of centuries a minimum of till now Shakespeare’s day of somebody youthful, merely like the greater youthful eco-friendly shoots of spring, and likewise of somebody who grow to be as yet green or immature. by the way, for Shakespeare a salad wasn’t merely lettuce with some dressing, yet a much greater complicated dish of chopped, blended and pro vegetables (its call comes from the Latin be conscious for salt); the be conscious grow to be extensively utilized for any vegetable that is blanketed in that dish. whether, Jan Freeman stated in a single of her be conscious columns for the Boston Globe back in April 2001 that the expression has shifted sense interior the US interior the previous 20 years or so. It now regularly refers to a era interior the previous while somebody grow to be on the top of their understanding or incomes capacity, of their heyday, no longer inevitably while they have been youthful. The shift isn’t so tricky to appreciate once you think of how few people actual understand their Shakespeare.