Famous Pirate Flags

Jolly Roger Pirate FlagJolly Roger Pirate Flag

Pirate flags flew from the ships of European pirates during the 17th and 18th centuries. There were many different designs, although the one that usually comes to mind is the skull and crossbones, a symbol of death that is also used to identify poisons. The flags are used primarily today for decorative purposes. Here’s a look at some of the different designs and the pirates believed to have flown these flags.

  Variants of the Pirate Flag - Jolly Roger

The Jolly Roger is the traditional skull and crossbones design on a black background. The origin of the name is difficult to determine and the word Jolly Roger can refer to any pirate’s flag. Most historians believe that it was called “jolly” because the skeleton’s head appears to be smiling and “old roger” was another name for the devil. 

Several pirates of the 17th and 18th century flew this flag including Black Sam Bellamy and Edward England. Bellamy was the wealthiest in recorded history, capturing over 50 ships during his short career that lasted little more than a year. He died in a ship wreck off the coast of Cape Cod. 

Bellamy’s shipwreck was found in 1984 and thousands of artifacts were retrieved including gold and precious stones. Edward England’s life may have served as the inspiration for Jack Sparrow in the Pirates of the Caribbean, although his story is similar to that of other pirates.

Like Sparrow’s, England’s ship was named the Pearl. His crew turned against him and he was marooned on a deserted island for a time, similar to one of the story lines in the Pirates series. 

Red Roger

Prior to the 17th and 18th centuries they were often a simple piece of red material with no design. One of the theories concerning the origin of the phrase Jolly Roger has to do with the French words for pretty and red. Those words are joli and rouge. Joli Rouge could have become Jolly Roger in English.

Pirates sometimes had several flags onboard. While they flew the skull and crossbones with the black background most of the time, they also had one with a red background. According to records of conversations with captured pirates, the red background meant that they would give “no quarter”. The captain and crew of the ship captured under this flag would all be killed.

The Flag of Long Ben Avery

Long Ben Avery Pirate Flag (Red Roger)Long Ben Avery Pirate Flag (Red Roger)

Long Ben Avery was another of the more successful pirates and unlike many of them, he was never captured. The last ship he is known to have captured was the treasure ship of the Grand Moghul of India. The booty on that ship would have made him one of the richest pirates of all times.

What he did afterward is a mystery, although the legends say that he married the daughter of the Grand Moghul and founded his own kingdom. His flag was different from most of the common pirate flags in a couple of ways.

The skull was in profile, does not appear to be smiling, and the skull wore a kerchief on its head, the headgear commonly worn by all of the crew, including the captain. Only on certain occasions would the captain put on his hat and the kerchief would be underneath. 

Other famous pirate flags include Black Beard’s, Black Bart’s and many others. You could easily create a large collection with all there are to choose from.

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Calico Jack’s Version

Calico Jacks Pirate FlagCalico Jacks Pirate Flag


Like most pirate flags, Calico Jack’s version included a smiling skull, but instead of the crossbones beneath the skull, there was a pair of crossed cutlasses, swords of the type that pirates usually used. Jack was famous not because of his success, but because two of his crew were women: Anne Bonny and Mary Read. They dressed, fought and swore like pirates. 


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