No one knows the origin of the name “Jolly Roger”; it may have come from the French word “joli rouge” meaning pretty red, a description of the bloody banner flown by early privateers. This term was corrupted to “Jolly Roger” by English buccaneers and was later applied to the black flag.
The earliest record of a Jolly Roger occurred around 1700 when the French pirate, Emanuel Wynne, flew a sable ensign with cross-bones, a death’s head and an hour glass, during an engagement with an English man-of-war off Jamaica. The hour glass may have been a hint that there was not much time for deliberation, a point reinforced by the skull and bones, a traditional symbol of death.
Blackbeard’s flag was one of the more unusual flags flown by the pirates. His flag had a skeleton holding an hour glass in one hand to signify that your time was running out. A dagger in the other hand and the heart with three drops of blood signified that blood would be drawn if you did not surrender. Horns and cloven feet on the skeleton signified that he was in league with the devil.