Skull and crossbones and beyond

What was the historical significance of the Jolly Roger ("Jolie Rouge," in the original French)?. The name may have also come from old sailor slang for the devil, being Old Roger. What did its symbols and images mean, and evoke? Fill in the table below with pirates and their respective flags.

The symbols used by pirates in creating their personal flags were often taken from symbols used on earlier non-personalized signal flags used to intimidate and to communicate intentions or warnings to ships they were attempting to take. Some of those symbols that appear here and their approximate meanings:

The skull and crossbones may have originally been taken from a common symbol that appeared on many mediaeval and renaissance gravestones. It was a natural symbol to represent death.
An hourglass, or an hourglass with wings: Your time is running out
Arm grasping sword or dagger: We will show no quarter
A dancing skeleton or a pirate toasting a skeleton: We have no fear of death
Spear: We promise a violent death
A speared heart or bleeding heart: We promise a painful, bloody death

Further Info: Often pirates would fly false colours, as a strategy to lure unsuspecting ships in close enough to open up with a broadside or board. From this practice comes the idiom "show your true colours." Pirate flags are well known and the subject of lore and legend. The truth is that pirates would not use a distinctive flag, but more often used a simple red flag or black flag, universal symbols of no quarter and take no prisoners. The distinctive flag was more of a personal banner in the same way a general or admiral today has a personal flag.

The Pirate	The Flag
Emanuel Wynne
Edward Teach "Blackbeard"
Henry Averys Banner
Jean Lafitte
Edward England
Bartholomew Roberts The letters under the skulls beneath Roberts' feet on the second flag stand for "A Barbadian's Head" and "A Martiniquean's Head". After being hunted by ships dispatched from Barbados and Martinique Roberts began a vendetta against the residents of both isles and celebrated it by hoisting a new flag.
Stede Bonnet
Calico Jack Rackam
Thomas Tew
Richard Worley
John Thomas Dulaien
Edward Low
John Quelch
Christopher Moody
Edmund Condent