> What does a Jolly Roger flag usually depict?And the answer: a skull and crossbones. During the 18th century, the Jolly Roger was the English name for the flagsflown to identify a pirate ship about to attack. Today we know the design as awhite skull and crossbones, on a black background.Photo credit: Federal Flags.The term "Jolly Roger" was first used by CharlesJohnson in 1724, in a book titled A General History of the Pirates. In it,Johnson draws the term from two pirate captains themselves, who used the term torefer to their own ships. Interestingly, because neither captain's flag actuallydonned the classically associated skull and crossbones, Jolly Roger was likely aterm that had been commonly used amongst pirates in reference to the simpleblack flag of piracy. The term "Old Roger," meanwhile, was a term that the British used to refer tothe devil, and was often depicted on a black flag. Any ship whose sails flewsuch a flag was to indicate that the signified dead was approaching, and wouldshow mercy if the crew surrendered. However, if a red flag was flown, it was toindicate that the pirates would show no mercy (i.e., you better hightail it outof there). Most of the time, pirates didn't proudly fly the pirate flag. Instead, theywould masquerade themselves with Spanish, French or Dutch colors until they werein range of their intended target. In time, the flag became a calling card forpirates, inspiring fear overseas. Learn more about the history of the Jolly Roger flag below.