25 Days of Holiday Songs 2025: “Five Pound Box Of Money” by Pearl Bailey

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Sometimes a person needs a little money! This is, like Eartha Kitt’s “Santa Baby,” one of those extra honest holiday songs about how giving may be better than receiving but the getting can feel pretty good, too, especially if the getting is in cash. Pearl Bailey’s delivery is just the right amount of tongue in cheek; she knows it’s a bold request of Santa, but she’s making it anyway, because times are tough, she needs the money and nobody’s invented GoFundMe yet. She does admit that money isn’t everything – this is probably why President Richard Nixon later appointed Bailey as America’s global Ambassador of Love – but “it’s much better with it than without it.”

“Five Pound Box Of Money” hit a peak in popularity in the late 1950s, not long after its release, and it was for an unusual reason. One of the biggest news stories of the time was the “payola” scandal, in which radio disc jockeys admitted to taking huge sums to play specific records on their shows. The biggest DJ in the business, Alan Freed, got fired in November of 1959, shortly after he and Dick Clark testified before a congressional committee investigating the scandal. Billboard noted that “Pearl Bailey has an unusually timely single out this year,” in that DJs had started leading into their news updates about the payola story by playing “Five Pound Box Of Money.” A few stations even held contests where they’d fill a five pound box with dimes, nickels, pennies and whoever guessed closest to the total amount of money got all the coins.

How much money would a five pound box hold? It depends on the box: a pound is a measurement of weight, and we’d really need to know how much room that box has for the $10 bills Bailey has in mind. “Five pound box” is likely a reference to a tradition in that era where friends of a woman who had just gotten engaged would bring a five-pound box of chocolates to her engagement party, but again, that doesn’t necessarily answer our question.

But here’s some alternate math that might help. The US Currency Education program says that each Federal Reserve note weighs about a gram, which means 454 bills of any denomination would weigh a pound. Let’s say Santa sent Pearl Bailey five pounds’ worth of ten dollar bills. That’s 2,270 notes, worth $22,700 in all. In today’s money that would be worth more than a quarter of a million dollars. Sounds like a merry Christmas to me.

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Brady Carlson
Brady Carlson
Brady Carlson is a writer and radio host from Madison, Wisconsin. more