Mandy, I’ve heard of Little Orphan Anny (or is it Annie?) and Sky King and his niece Penny. But I’ve never heard of ‘penny anny,’ although I have heard of Ante Mame (or is it Auntie?). What you probably meant was ‘penny-ante.’ ‘Penny anny’ is a classic example of what is known as a ‘mondegreen,’ a word or phrase resulting from the mishearing or misinterpretation of a statement or song lyric (“Our Father, which art in Heaven. HAROLD be thy name”). There have been a lot of these around here lately, and I occasionally discover one of my own.
I’m going to post this under the correct spelling, just in case someone might want to look it up in the future.
Ken G – August 30, 2004
PENNY-ANTE (adjective) and PENNY ANTE (noun) each have two meanings. First, it is a poker game in which the highest bet was originally limited to a penny and later on just a small sum. The ‘ante’ is a fixed but arbitrary stake put into the pot by each player before the deal. A penny is an insignificant amount of money and thus these games were played more for fun than high stakes. Since a penny of ante is a trifling amount, the expression took on a second slang figurative meaning of anything or anyone of small importance, dealings on a small scale or with picayune/trifling sums involved. It also came to mean insignificant, unimportant, small-time, contemptible, trivial. The term dates back to mid-19th-century America.
(Picturesque Expressions by Urdang, Facts on File Encyclopedia of Word and Phrase Origins, Oxford English Dictionary)<1946 “Compared to the man Bilbo, 63-year-old John Rankin is strictly PENNY ANTE.”—‘Negro Digest,’ August>
<1996 “Governments are complying, granting monopolies over information and information products that make the monopolies of the 19th-century robber barons look like PENNY-ANTE operations.”—‘New York Times,’ 31 March>
<1997 “I'm sure he [[Mike Espy, Secretary of Agriculture under Clinton]] probably thought it was PENNY-ANTE stuff and that nobody would pay that much attention and was confident that none of these gifts, football tickets in the skybox, something else here, plane trips and that kind of thing, was enough to corrupt him because he was confident in his own character.”–‘Gannett News Service,’ 8 September>
Ken G – August 20, 2004