The Jolly Roger is a black flag with a white skull and crossbones. The Jolly Roger is a pirate flag that first appeared in the 1710s, though the earliest such flags seem to have sported an entire skeleton. Most pirate flags were either entirely black or entirely red, with no decoration. When pirates flew a black flag it indicated that the attacking pirates would spare the sailors on the ship being attacked if the sailors did not resist. A red pirate flag indicated that the pirates were attacking without mercy. The phrase Jolly Roger had been around for over a hundred years by the time the first Jolly Roger pirate flag appeared. Originally, Jolly Roger was a generic term for a happy fellow. It appears that pirates called this skull and bones flag the Jolly Roger in reference to the grinning skull. Today, Jolly Roger connotes the idea of swashbuckling piracy or lawlessness, and the term is often used in the names of businesses and in literary titles. Note that both words are capitalized in Jolly Roger.
Examples
At first, they considered naming the gallery the “Jolly Roger” for the gallery’s backer, Robert C. Scull, a collector and taxi tycoon. (The New York Times)
When first mate James of the Jolly Roger meets the yearning, idealistic young fairy Tinkerbell, their star-crossed romance brings together the entire population of Neverland, from the mischievous Dream Weaver fairies to the mighty Natives, and even a colony of scavenging boys whose leader fell from the sky.” (The Pittsburgh Post-Gazette)
The FCC Hoists the Jolly Roger on Your Cable Box (The Wall Street Journal)
Members of the Bristol City Council Licensing Committee are considering whether to revoke the licence of the Jolly Roger pub in Easton. (The Bristol Post)
A Jolly Roger flag flown atop a World War Two submarine has resurfaced – after going missing for 40 years. (The Daily Mail)