Kevin David Creative

It’s the one cloud in a clear blue sky that blots out the sun and leaves you shivering. The tiniest of typos enough to send an entire marketing team into a tailspin. Nothing short of an upside-down airplane can induce the same sort of stomach-turning sickness as a printing error. But one famous production folly has been met with the stamp of approval from wealthy collectors to prime-time cartoons.

The “Inverted Jenny” is a U.S. postage stamp produced in 1918 showing an inverted image of a blue airplane. At the time, delivering mail by air was a novel and very expensive endeavor. To fend off the frenzy of angry customers who balked at the 24 cent service (traditional stamps were a mere three cents), the Post Office commissioned Clair Aubrey Huston, Chief Stamp Designer, to create an image that would propel its new air division to new heights.

But the two-color printing process required to produce the image was unreliable, resulting in a plane that was far from Wright-side up. While the rest of the ruined stock was intentionally destroyed, a collector named William T. Robey was able to purchase a complete sheet of 100 inverted stamps from a hapless post office clerk who had never seen an airplane before.

More than 100 years later, the stamps are still auctioned and privately sold for millions of dollars, ensuring Jenny’s rightful place in the wrong side of Philately history (I had to Google it too. It’s the study of postage stamps).

In an interview with the Smithsonian, Daniel Piazza, a curator at the Postal Museum, credits the stamp’s enduring popularity to its symbolic and illogical nature.

“It’s the romance of early aviation, it’s the dramatic image of the plane flying upside down, it’s the red white and blue colors,” Piazza says. “It just has so much going for it: The end of World War I, the beginning of civilian aviation, carrying the mail by the air.”

So if you’ve ever been part of a project that has gone sideways, be sure to save at least one proof on the off chance the goof turns to gold.