Life Lessons from Hit Songs

Bing Crosby didn’t think he was giving financial advice.

But in 1936, when he sang about turning rainy days into pennies from heaven, he “coined” a truism about investing: opportunity can arrive when you least expect it. In “Pennies from Heaven,” it arrived disguised as bad weather.

Crosby’s depression-era audience knew all about financial hardship. But the song suggested that somewhere above the clouds, abundance was still intact, still falling, and still available to anyone willing to stand in the rain long enough to catch it.

Toe-Tapping Personal Finance¹

As it turns out, the American songbook is full of financial wisdom—some of it intentional, most of it accidental, and all of it surprisingly relevant to the choices we make with our money and spiritually today.

1. “Pennies from Heaven” by Bing Crosby (1936)

Bing Crosby sang the song in the film with the same name. Released during the Great Depression, the song talks about the financial freedom of the Roaring ’20s yet provides hope that the country will emerge stronger and better than before.

2. “Can’t Buy Me Love” by The Beatles (1964)

Sure, money can buy you diamond rings, but the one thing money can’t get you—no matter how much of it you have—is love. It’s a simple but crucial lesson: Money can get you nice things, but the most important things in life can’t be bought.

3. “Taxman” by the Beatles (1966)

“Let me tell you how it will be. There’s one for you, nineteen for me.” Without a financial strategy in place, it can feel like taxes are the issue. The top federal marginal tax rate in 1966 was 70%. This rate applied to taxable income over $200,000 for married couples, which would be about $1.9 million today.

4. “O Come, All Ye Faithful” (~1743)

This hymn is a celebration of the birth of Christ. But in many ways, it shows that the wealth accumulated through spiritual faith will far exceed anything that you have in a bank account.

5. “Sittin’ in the Sun” by Louis Armstrong (1953)

This one may not be as well-known as the others, but it belongs on the list. Armstrong paints a simple picture of sitting in the golden sunshine, feeling the “summer breeze,” and being happy about how he’s prepared for the future.

While many of us can hum along to these tunes, charm has its limits.

“Pennies from Heaven” won’t help you navigate a Roth conversion. “Taxman” identifies the problem but offers no solutions. And “O Come, All Ye Faithful” shows what’s important, but you have to guide your own spiritual journey.

When it comes to the real decisions—how to save, when to invest, and how to build for the future—you need more than a good lyric. We’re here to help in any way we can.