How accurate is the stereotypical depiction of a pirate?

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So just how accurate is the image of the peg-legged, eye-patched, bandanna and tricorn hat wearing pirate with a parrot on his shoulder who frequently says things like "Arr, arr, me mateys!" and "Avast, ye scallywags!" while hoisting the Jolly Roger and looking for buried treasure or alternatively the dashing, mischievous, half-drunk Captain Jack Sparrow type of pirate with the mannerisms of Keith Richards who really isn't so bad?

One common reaction people have who suspect the above image might not be accurate is to assume that the reality was probably almost completely opposite and historical pirates were probably nothing but vicious, unromantic cutthroats and criminals and they must have been viewed by contemporaries similarly to how we view common armed robbers or maybe Somalian pirates today, and it wasn't until long after the heyday of piracy that this more romantic view became popular. The truth is somewhere in the middle and pirates were viewed in numerous different ways by different people both during and after their own time.

I think the best way to get a full overview of how the modern image of pirates evolved and how it matched reality is to start at the beginning and go from there. The first widely popular and printed book written about pirates/buccaneers/privateers (the legal distinctions between these were often very shady at least until the early 18th century) was published in Dutch in 1678 by the Dutch or French barber-surgeon Alexandre Exquemelin and called The Buccaneers of America. It was so popular that it was reprinted in numerous editions and quickly translated into German, Spanish, English and French by 1686. This was well within the heyday of piracy and buccaneering and almost 40 years before the pirates Blackbeard and Bartholomew Roberts would prey on shipping. So what was the image of piracy and buccaneering presented in this book that so fascinated normal people mostly living in Europe?

In addition to detailed descriptions of the Americas and the lifestyle of the buccaneers, the book is extremely violent and basically does not present a "good" image of any of the buccaneers or their leaders. The former buccaneer captain Henry Morgan, who by the time the book was translated into English in 1684 had sold out his former buccaneer allies and actually been knighted by Charles II, so much disliked the way he was portrayed that he successfully sued the English publishers of the book for libel and likely won due to political influence. Another buccaneer described in the book was Roche Braziliano who was said to have roasted alive Spanish farmers who refused to show him where they kept their hogs and most memorably the French buccaneer Francois l'Olonnais is said to have ripped out the heart of one Spanish captive in a frenzied rage and gnawed at it when he wouldn't show him a secret route to the next town. The book extensively describes many other brutal tortures the buccaneers inflicted on Spanish captives to make them confess where they had hidden their valuables after sacking a town. One of the most common tortures described in the book was borrowed from the Spanish Inquisition and known as the "strappado" in which the victim's arms were tied behind their back and they were suspended that way and then dropped multiple times to the ground until their arms and shoulders broke causing severe permanent damage or death, not to mention excruciating pain. The motive behind these tortures may in fact be one of the grim origins of the pirates' fabled search for hidden treasure.

But The Buccaneers of America wasn't just about violence, it was also full of adventures and large scale attacks by buccaneers against fortified Spanish towns and forts and there was indeed lots of gold and jewels and pieces of eight to be had and it captured people's imaginations just like it does today. This was also the period in which attacks against well-armed Spanish galleons such as the "great urca" treasure ship that sailed annually from Spain to the Gulf of Honduras carrying vast shipments of wealth were a frequent target (The Buccaneer's Realm, Little, p. 73). The image of pirates attacking Spanish galleons loaded with chests of gold and jewels comes from things like this.

Another iconic trope associated with pirates discussed in The Buccaneers of America is the heavy drinking and debauchery the they did in their spare time. This was the era in which the famous French island of Tortuga off the north coast of Hispaniola (Haiti) offered a safe refuge to many buccaneers and a booming town in which they could go to spend their sometimes very substantial stolen wealth on alcohol and women. Some other notable "buccaneer havens" during this time were Port Royal in Jamaica (although this went into decline after 1671 and the English began to crack down on buccaneering) and the French town of Petit-Goave on the western coast of Hispaniola. In such places, violence and brawling were indeed common and this is vividly described by Exquemelin:

Captain Rock sailed for Jamaica with his prize, and lorded it there with his mates until all was gone. For that is the way with these buccaneers -- whenever they have hold of something, they don't keep it for long. They are busy dicing, whoring and drinking so long as they have anything to spend. Some of them will get through a good two or three thousand pieces of eight in a day -- and next day not have a shirt to their back. I have seen a man in Jamaica give 500 pieces of eight to a whore, just to see her naked. Yes, and many other impieties.

My own master often used to buy a butt of wine and set it in the middle of the street with the barrel-head knocked in, and stand barring the way. Every passer-by had to drink with him, or he'd have shot them dead with a gun he kept handy. Once he bought a cask of butter and threw the stuff at everyone who came by, bedaubing their clothes or their head, wherever best he could reach.

... Even the man I have just been speaking about, the one who gave the whore so much money to see her naked and at that time had a good 3,000 pieces of eight -- three months later he was sold for his debts, by a man in whose house he had spent most of his money.

Now, what are some ways in which the image shown in this book differs from the common conception of pirates? One major difference is that the “pirates” or buccaneers during this time almost always used the pretext of lawful privateering in order to plunder ships and settlements. The late 17th century was a period in which there were many frequent wars between European powers and during these wars privateering commissions or letters of marque would be granted by local governors in the Caribbean (usually in exchange for payment and a share of the profits) to the many buccaneers hanging around in port towns like Tortuga, Petit-Goave and Port Royal authorizing them to plunder enemy shipping and settlements. For the French and English the enemy usually included Spain, and Spain was a very lucrative target. Even when France or England weren’t technically at war with Spain, these commissions were still often used as a pretext for piratical attacks to give them at least a mild veneer of legitimacy. Because of this the Jolly Roger or skull and crossbones flag was not used at this time because there was no need for it. Buccaneers who claimed to have French or English privateering commissions would fly a French or English flag when they attacked Spanish ships or towns and claim to be representing those countries.

However, this began to change in the last quarter of the 17th century and by the end of the century there were more peaceful relations between many European countries and both sides realized that buccaneers were extremely mutually harmful and destructive to trade even in peacetime and they increasingly began cracking down on them. Legitimate-looking privateering commissions became harder and harder to get from even the most corrupt local governors. Then, just as things were getting quite bleak for these erstwhile buccaneers, the War of Spanish Succession and Queen Anne’s War broke out in Europe between England and Spain lasting from 1702-1714 and this provided many opportunities for buccaneers to once again have their attacks backed up with legitimate privateering commissions.

But it was not to last. When the Spanish War of Succession ended in 1714, except for a brief period from 1718-20, England and Spain were once again at peace and this time the British and French in conjunction with the Spanish sought to put an end to piracy once and for all. Pirates were declared hostis humani generis (enemies of mankind) for which the punishment was death by hanging. At this same time, many English sailors who had been employed in the greatly expanded navies during the Spanish War of Succession and Queen Anne’s War were now unemployed and desperate. Many turned to piracy. This final period lasted from about 1715 to 1725 and it was essentially the last brief and bitter hurrah of the golden age of piracy. By 1725 European piracy had been virtually eradicated from the Caribbean and Indian oceans.