The name Jolly Roger first appears firmly in Captain Charles Johnson’s 1724 A General History of the Pirates, where Bartholomew Roberts and Francis Spriggs both call their quite different flags by it, and neither featured a skull and crossbones. Theories trace it to Old Roger, slang for the devil, to the French jolie rouge for the red flags of privateers, or to roger meaning rogue. Black with a white skull became standard only around 1730. A French log from 1687 describes a red skull and crossbones flag used on land, and Barbary corsairs flew green flags with skulls. Pirates approached under false national colors, then raised the black flag to offer quarter if the target struck its colors, and a red flag, the bloody flag, if it resisted.

Famous designs are later myths: contemporaries describe Blackbeard flying only a simple death’s head, and Calico Jack Rackham was flying a white pennant when captured, not crossed cutlasses. A 1959 book by German author Hans Leip helped spread such fictional attributions. In 1914 First Sea Lord Arthur Wilson called submarines damned un-English and wanted their crews hanged as pirates, so Max Horton flew a Jolly Roger from HMS E9 after sinking a German cruiser, starting a tradition of stitching patrol tallies onto the flag.

• Pirates feared no legal limits, while privateers with letters of marque had to accept surrender and take prisoners of war.
• Submarine flags used red bars for warships, white bars for merchant ships, and a dagger for cloak and dagger missions.
• HMS Proteus added a can opener after its diving planes ripped open an Italian destroyer that tried to ram it.
• HMS Conqueror flew a Jolly Roger in the Falklands War, and USS Jimmy Carter has returned to port flying one.
• In 2025 Indonesian truck drivers flew the straw hat flag from One Piece instead of the national flag, and officials called it treason.