The origins of the name "Jolly Roger" are difficult to establish. It is likely derived from the fact that devil was often referred to as "Old Roger", and so the flag suggested the wrath of the devil. The classic skull and bones design was also often used in the Captain's log to indicate the death of a sailor. This flag was an important part of the pirate's armory, and is considered one of the earliest forms of psychological warfare.

In popular legend, it seems that every pirate flag consisted of a skull above two crossed bones. This was generally not the case, as the Captain and his crew often wanted their own flag. While it is true that most pirate flags had the skull and crossbones on them, they often had other images such as skeletons, swords, hourglasses, goblets, and hearts.

One of the most famous pirates was "Black Bart", otherwise known as Bartholomew Roberts. He was originally from Wales, and in his 4 year career captured well over 400 ships and accumulated incredible wealth. It is said that he was a brilliant, fearless, and innovative seaman. His fleet scoured the seas looking for treasure, and he inspired fear and dread in governments and citizens alike.

The governments of the Caribbean islands of Barbados and Martinique were keen to see an end to his seafaring activities. In 1720, "Black Bart" captured the governor of Martinique and hung him from the mast of his ship. The flag he would fly represented the personal vendetta he had against the islands and its inhabitants. His flag consisted of an image of a man (presumably Bart) with a flaming sword in hand, standing with a skull under each foot. The letters "ABH" and "AMH" were inscribed under the skulls, and stood for "A Bahamian's Head" and "A Martinicans Head".

Be afraid. Be very afraid.