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Edward Low was a particularly ruthless pirate who had a long and successful career (by pirate standards). He took over a hundred ships over the course of two years, from 1722 to 1724. A cruel man, he was eventually kicked out by his own men and set adrift in a small boat. His flag was black with a red skeleton.

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The Flag of Stede Bonnet, "The Gentleman Pirate"

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The Flag of Stede Bonnet, "The Gentleman Pirate"

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Ever notice how some people just seem to wind up in the wrong line of work? During the Golden Age of Piracy, Stede Bonnet was one such man. A wealthy planter from Barbados, Bonnet got sick of his nagging wife. He did the only logical thing: he bought a ship, hired some men and sailed out to become a pirate. The only problem was that he didn't know one end of the ship from the other! Fortunately he soon fell in with none other than Blackbeard himself, who showed the rich landlubber the ropes. Bonnet's flag was black with a white skull over a bone in the middle: on either side of the skull were a dagger and a heart.

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John "Calico Jack" Rackham had a short and largely unimpressive pirate career between 1718 and 1720. Today, he is really only remembered for two reasons. First of all, he had two female pirates on his ship: Anne Bonny and Mary Read. It caused quite a scandal that women could take up pistols and cutlasses and fight and swear their way into full membership on a pirate vessel! The second reason was his very cool pirate flag: a black jack that showed a skull over crossed cutlasses. In spite of the fact that other pirates were more successful, his flag has gained fame as "the" pirate flag

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The Flag of Bartholomew "Black Bart" Roberts, Part Two

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The Flag of Bartholomew "Black Bart" Roberts, Part Two

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"Black Bart" Roberts hated the islands of Barbados and Martinique, as their colonial governors had dared to send out armed ships to try and capture him. Whenever he captured ships originating from either place, he was especially harsh with the captain and crews. He even made a special flag to make his point: a black flag with a white pirate (representing Roberts) standing on two skulls. Underneath were the white letters ABH and AMH. This stood for "A Barbadian's Head" and "A Martinico's Head."

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The Flag of Bartholomew "Black Bart" Roberts, Part One

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The Flag of Bartholomew "Black Bart" Roberts, Part One

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If you go by loot alone, Henry Avery was the most successful pirate of his time, but if you go by number of ships captured, then Bartholomew "Black Bart" Roberts beats him by a nautical mile. Black Bart captured some 400 ships in his three-year career, in which he ranged from Brazil to Newfoundland, to the Caribbean and Africa. Black Bart used several flags during this time. The one usually associated with him was black with a white skeleton and white pirate holding an hourglass between them: it meant that time was running out for his victims.

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Henry "Long Ben" Avery had a short but impresive career as a pirate. He only ever captured a dozen ships or so, but one of them was nothing less than the Ganj-i-Sawai, the treasure ship of the Grand Moghiul of India. The capture of that ship  alone puts Long Ben at or near the top of the list of all-time richest pirates. He disappeared not long after: according to legends at the time, he had founded his own kingdom, married the beautiful daughter of the Grand Moghul and had his own war fleet of 40 ships. Avery's flag showed a skull wearing a kerchief in profile over crossbones.

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If you were sailing about in the Caribbean or southeastern coast of North America in 1718 and saw a ship flying a black flag with a white, horned skeleton holding an hourglass and spearing a heart, you were in trouble. The captain of the ship was none other than Edward "Blackbeard" Thatch, the most infamous pirate of his generation. Blackbeard knew how to inspire fear: in battle, he would put smoking fuses in his long black hair and beard. They would cause him to be wreathed in smoke, giving him a demonic appearance. His flag was scary, too: the skeleton spearing the heart meant that no quarter would be given.