"If you're going to take a risk at all, you might as well make it a big risk."

From an old British expression (thus "pound" instead of "dollar"); the original reference was probably to theft (though this is not certain), saying that being arrested ("taken in") for stealing a small amount is just as bad as for a large amount, so you may as well steal a lot and hope to get away with it.

An equivalent expression is, "As well hanged for a sheep as a lamb", where it's implied that you are stealing the animal. If the punishment for failure is the same, you may as well try for the largest possible reward.

The phrase is often misused with reference to a punishment that is out of proportion to a crime, but this is not the actual meaning.
"I could get fired just for talking to you. Well... in for a penny, in for a pound! Come on in."
by Keenath January 17, 2008
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An expression of 70's street culture that means that if you participate even slightly in something, you are fully involved in the consequences.
Frank: "Charlie got 5 years for that liquor store hold-up, and he was just the look-out!"

Sam: "Well, you know what they say, 'in for a penny, in for a pound!'"
by PJ Poppyjoe June 7, 2005
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A sexualized version of "in for a penny, in for a pound." Means almost the same thing as the original saying but in a sexual context as aforementioned. In context, it references sex with or without protection (in this case, without), and since it was done before might as well double down and do it again regardless of the consequences.

This was used in Team Four Star's, Dragon Ball Z Abridged: Episode 60 Epilogue.
Bulma: "But after the first time, I just thought; well, in for a penny, in for a pounding."
Trunks: "Ahhh!"
Bulma: "And I really was."
by 7N_Shepard December 27, 2018
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A wager that is considered a sure thing or a likely scenario.
I'd bet you pennies to pounds the rams will win the super bowl
by Kootss March 26, 2019
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Making a very small or worthless contribution (see also: putting dimes in the dollar jar for American)
She might as well be putting pennies in the pound jar with the help she's contributing.
by Ellgrace June 23, 2020
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Where someone compulsively saves money by buying super-cheap-priced foods like crackers and white bread, not caring/realizing that these salty/sugary/"empty-carbs" foods will make him gain unhealthy weight in a hurry. Ben Franklin was always sagely expounding about stuff like this, and just look at da deplorable "tubby" shape HE was in!
That balloon-bodied dude with clogged arteries in the ER never eats health-food stuff "'cuz it costs too much" --- talk about "penny-wise and pound-foolish" --- what good is being a penny-pincher and "fattening" your bank account if you're also gradually fattening YOURSELF in the process???
by QuacksO August 14, 2018
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1. An example of poor customer service by an apathetic bartender;

Being the only person/group of people stood at the bar waiting to be served while the bartender/dosy blonde barmaid is checking his/her e-mails and/or facebook, completely oblivious to his/her waiting patrons.
Steve: "Barkeep, oh barkeep... We're in need of some intoxicants... STAT!"

Sarah: "Tell me about it. Ya Can't get a penny for a pound round 'ere mate!"
by robotmafia October 5, 2010
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