Pirates have sailed the high seas as long as ships have been in the ocean. And pirates' well deserved reputation of plunder, brutality and showing no quarter has sailed along with them.
To provide fair - or fear - warning, symbols have been used to mark pirate ships and the intention of those on board. Vikings, for example, with an unsavory reputation as raiders, placed dragon carvings at the prow of their ships to give warning and instill fear to any who crossed their path.
Beginning sometime in the 1700s pirates began using skull and crossbones' flags to identify their ships and intentions. The symbol had long been used to mark homes of those suffering from plaque and as a clear warning to stay away. An early pirate named Emanuel Wynne may have been the first to take the skull and crossbones symbol and use it as his personal flag. Wynee's flag boasted a skull and crossbones over an hourglass to let victims know they did not have long to live - and their precious lives would be cut even shorter if they resisted.
Flags were personal and most pirates had their own design. Calico Jack Rackham used a skull and crossed swords for his flag while pirate Edward Low preferred a red skeleton. Some pirates, perhaps less creative, flew a plain black flag to give potential victims a chance to surrender. If they did not, then a red flag would be raised indicating an attack was imminent.
There is still no clear cut explanation for how pirate flags came to be called Jolly Rogers. One explanation is that the French, who had their own share of pirates, used the wry term jolli rouge, or pretty red to describe their bloody colored banners. Another explanation is rooted in an understanding of early English. The word jolly referred to bravery or courage, as in the song "For He's A Jolly Good Fellow." Jolly then refers to battle courage of pirates, known for fighting to the last man. The word roger was, centuries ago, used to indicate a devil, vagabond or rogue. A grinning devil, often referred as Old Roger, would partake in mayhem.
Pirates were a vicious lot, and they used Jolly Roger flags, complete with grinning skull and crossbones, as clear warning - surrender or die.