Origins
The origin of the pirate flag has been lost. It is thought that pirates originally used a red flag, which was also common in naval warfare, to signal that no quarter would be given. This red flag was called Joli Rouge (pretty red) by the French, and may have been corrupted into English as Jolly Roger. From the red flag it seems that individual pirates began to develop their own personal flags in order to terrify their foes into a quick surrender. In contrast with the well known red flag, they used the black flag of quarantine and disease as the base, with the universal symbol for death, the skull and bones, and modified it to suit their individual tastes. The skull and bones was also used in captains' logbooks to indicate the death of a sailor.
A third possibility is that Jolly Roger derived from 'Old Roger' as a term for the devil. That the "Jolly Roger" flag was called the "Old Roger" flag in 1723 supports the third proposed origin. A news report in Weekly Journal or British Gazetteer (London, England), Saturday, October 19, 1723; Issue LVII, page 2, col. 1 reads: "Parts of the West-Indies. Rhode-Island, July 26. This Day, 26 of the Pyrates taken by his Majesty Ship the Greyhound, Captain Solgard, were executed here. Some of them delivered what they had to say in Writing, and most of them said something at the Place of Execution, advising all People, young ones especially, to take warning by their unhappy Fate, and to avoid the Crimes that brought them to it. Their black Flag, under which they had committed abundance of Pyracies and Murders, was affix'd to one Corner of the Gallows. It had in it the Portraiture of Death, with an Hour-Glass in one Hand, and a Dart in the other, striking into a Heart, and three Drops of Blood delineated as falling from it. This Flag they called Old Roger, and us'd to say, They would live and die under it."
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