Pirates

The "Jolly Roger" is used to refer to the skull and crossbones flag (white on black) which is associated with Caribbean pirates. Although I think the name comes from "jolie rouge" (Fr: "pretty red") which referred to an earlier all-red flag reportedly used by some pirates.
Paul Adams 29 November 1995

---

There's a lot of controversy about this, but the article I read from an information column called The Straight Dope (I'm doing this from memory) said that one of the origins might be from the title "Ali Rajah" given to one of the pirates.
Dipesh Navsaria 29 November 1995

---

Pirate ships in the 15th to 17th Centuries which plied the Atlantic as far east as Madagascar were often run as self-contained floating democracies (the captain was usually only in undisputed charge during a battle), and each captain and ship generally bore his or its own flag. Almost all were white or white and red on black, and featured similar elements: skulls or skeletons (symbolizing death; the pirate wanted to project fearlessness in the face of death, and some flags pictured the captain toasting, dancing with, or literally conquering the skeletal Death), swords and cannon (obvious symbolism), treasure chests (ditto), hearts (often pierced, to symbolize "no mercy"), and pirates themselves. The classic "skull-and-crossbones" was almost certainly among these designs. (I don't know which pirate actually flew it. I know Calico Jack Rackham flew a skull and crossed *swords*, but that's as close as I've found in my research.)

In the early days of the so-called "Golden Age of Piracy" (mid-to-late 1500's), pirates (especially French boucaniers, or buccaneers) kept two battle flags, one plain red and one plain black. Before a battle, the captain would hoist one or the other to show whether quarter was being given (for the non-English speakers, this is an archaic expression meaning whether or not prisoners would be taken). The red flag meant "no quarter" (no prisoners, slaughter every one of the enemy). As pirate warfare became more brutal, the two different flags were generally replaced by just one, the (usually) black flag, which was defaced as above. But the flag kept the French nickname given to the red flag: joli rouge. This was angliciz