Nothing was probably more terrifying for sailors during the “Golden Age of Piracy” (18th Century) than spotting a black flag with the skull and crossbones sailing towards you.
Jolly Roger is the traditional English name for the flags flown to identify a pirate ship about to attack during the early 18th century. The flag most commonly identified as the Jolly Roger that we think of today is the skull and crossbones symbol on a black flag, was used during the 1700’s by a number of pirate captains including “Black Sam” Bellamy, Edward England, and John Taylor.
Use of the term Jolly Roger in reference to pirate flags goes back to at least Charles Johnson’s “A General History of the Pyrates” published in Britain around 1724. Johnson specifically states that Bartholomew Roberts (1721) and Francis Spriggs (1723) as having named their flag “Jolly Roger”. While Spriggs and Roberts used the same name for their flags, their flag designs were quite different, suggesting that “Jolly Roger” was already being used generically for black pirate flags rather than a name for any single specific design. Neither Spriggs’ nor Roberts’ Jolly Roger consisted of a skull and crossbones. Richard Hawkins, who was captured by pirates in 1724, reported that the pirates had a black flag bearing the figure of a skeleton stabbing a heart with a spear, which they named “Jolly Roger”.
The origin of the name is unclear. Jolly Roger had been a generic term for a jovial, carefree man since at least the 17th century and the existing term seems to have been applied to the skeleton or grinning skull in these flags by the early 18th century. In 1703, a pirate named John Quelch was reported to have been flying the “Old Roger” off Brazil, “Old Roger” being a nickname for the devil. There is also reference to the privateers of 1694 using a red flag known as “Red Jack”. The french privateers would be operating under what they called the “Jolie Rouge” which translates as jolly red. From this it seems a simple step to the Anglicisation ‘Jolly Roger’
Pirates did not always fly the Jolly Roger, like other vessels, pirate ships usually stocked a variety of different flags, and would normally fly false colors or no colors until they had their prey within firing range. When the pirates’ intended victim was within range, the Jolly Roger would be raised, often simultaneously with a warning shot. The flag was probably intended as communication of the pirates’ identity, which may have given target ships an opportunity to change their mind and surrender without a fight.
Flying a Jolly Roger was an obvious way to prove oneself a pirate. Possessing one was considered proof that one was a criminal pirate rather than something more legitimate; only a pirate would be daring enough to use the Jolly Roger, as he was already under threat of execution. Today, the flag is still synonymous with piracy.