The skull and crossbones image which the Jolly Roger flag is based on was used to represent death long before the era of pirates.
It was seen a lot during plagues to warn that someone inside a house, ship, or room was afflicted.
Because the skull-and-crossbones had come to mean “danger, stay away,” it seemed like a fitting accessory to be hoisted on a pirate ship. Why was it called the “Jolly Roger” when its meaning was anything but jolly, you might well ask?
Go ahead and ask. We’ll wait for you.
There are several theories that we’ve collected from some otherwise reliable fact mongers. Here they are arranged in order of what we consider least likely to most likely:
The name came from the French joli rouge, meaning “pretty red.”
Supposedly, pirates were in the practice of dipping their flags in red paint or even blood. However, since the name refers to a black-and-white flag with no trace of red, this sounds like after-the-fact linguistic gymnastics.
Admittedly, some pirate ships began displaying a red Jolly Roger to indicate that they were even more dangerous than ordinary pirates. However, the term “Jolly Roger” predates this practice.
Here’s what we consider most likely: The term “Roger” had been in use in the English language since the middle ages, meaning “devil” or “rogue.” Although today we define the word “jolly” as “happy” or “jovial,” the term once meant “brave.”
Thus, the song “For He’s a Jolly Good Fellow” was meant to pay tribute to someone’s bravery, not his cheerfulness.
We think “Jolly Roger” makes perfect sense as a name for a skeleton flying above a throng of brave rogues.
That’s our preferred story, and we’re sticking to it.