The Online Etymology Dictionary says that it was first recorded in 1768: http://www.etymonline.com/index.php?search=%22pretty+penny%22&searchmode=none This has a more complete explanation, towards the bottom: http://www.randomhouse.com/wotd/index.pperl?date=20011023
"Penny pincher" is the slang term for a stingy person.
penny for your thoughts
A bad penny is an idiom for something which is unpleasant or unwanted, especially something which appears at an undesirable time.
It originates from: The Midsummer Night's Dream by Shakespeare - if two people are together with one person's cheek right by another person's cheek (jowl), they are pretty close indeed.
The phrase means that something is very expensive. The origin comes from a gold penny that was minted in the 1200's that was worth 20 silver pennies. Because it was gold, it was a pretty penny, and if it cost a pretty penny, it was expensive indeed.
"A penny" isn't an idiom - it's just a one-cent American coin.
"Penny pincher" is the slang term for a stingy person.
Shakespear Play
penny for your thoughts
Pretty Penny was created in 1995.
confucius...
It's TO SPEND A PENNY. It means to urinate. In the old days, public toilets cost a penny.
A bad penny is an idiom for something which is unpleasant or unwanted, especially something which appears at an undesirable time.
Where jcpenny orignated
what is origin of the idioum race against the clock
It means to urinate. At one time, public rest rooms cost a penny to use.
"Penniless" is not an idiom. It means that you don't have a penny to spend. It's used as an exaggeration to mean that you don't have any money.