15 Real Pirates That Make Jack Sparrow Look Like A Joke

It's almost a rule of entertainment at this point: we love rebels, and there is no historical figure that embodies that rebellious spirit like a pirate. Throughout history, pirates have swashbuckled, sailed, apprised, and even hacked their way into our hearts, minds and social consciousness. That's probably why the world fell in love with the fictitious pirates in Pirates of the Caribbean. We love those movies so much, we're even willing to forgive Pirates 4, to the point that we're all excited for a Pirates 5. Seriously, that's how much we love pirates. Their stories, even if they don't end well or represent the best sorts of people, appeal to our sense of excitement and adventure.

While we'll always have a place in our hearts for Jack Sparrow and the gang aboard the fictitious Black Pearl, the history of piracy dates back several thousand years, and we can make literally hundreds of new pirate franchises simply by mining world history. That being said, here are fifteen real life pirates that would make for excellent protagonists in their own movies or franchises.


15 Hayreddin Barbarossa


Hayreddin Barbarossa was a pirate who sailed the Mediterranean Sea for decades with his brothers, one of whom actually lost an arm fighting the Spanish. While the Barbarossa brothers as a whole could make up several pirate movies that would clean up at the box office, Hayreddin deserves special credit. For one, after his one armed brother died (in truly awesome fashion, by the way), Hayreddin took over his position as the person in charge of the entire Barbary Coast and proceeded to basically go to war with the Spanish with an army of Muslim followers. For another, he spent the rest of his life fighting his Christian enemies, to the point where there was a fleet called the Holy League that was specifically coming for him.

I don't know about you, but that sounds like a movie franchise worth watching. It's not like Hayreddin Barbarossa hasn't shown up in pop culture before. Even discounting the fact that Pirates of the Caribbean has Hector Barbossa, a Barbarossa stand in played by Geoffrey Rush, there's a comic book series based on him and a video game character literally named after him in Bravely Default. We've already got fictional versions of this guy, so we may as well get a movie based on the real man.

14 The Sea Dog of Queen Elizabeth

Sir Francis Drake, aka the Sea Dog of Queen Elizabeth, is like a real life Davos Seaworth: a man living on the edge who swashbuckled and fought his way into greatness, legend and the heart of a ruling power. He was the first English sailor to ever successfully circumnavigate the globe, and during that three year trip, he lost four out of his five boats, had to execute some of his crew for mutiny, and got into fights with the Spanish, eventually capturing a vessel that was loaded with treasure. Needless to say, Queen Elizabeth was so happy, she knighted the man. After that, he became second in command of the English army in the fight against the Spanish, who labeled him a pirate known as El Draque. King Philip of Spain had a 20,000 ducat prize on his life, which translates to something like four million pounds. That's 6.5 million US dollars, by the way, so this guy was a big deal.

Needless to say, I'd watch this movie. Sure, I'd leave out his eventual death by dysentery, because that's not necessarily how the movie should end, but this knight would make for some incredible movie action. He's already part of the story of Uncharted with his fictional descendant Nathan Drake, and he's already been the subject of a few movies. However, I want him to get the full Pirates treatment: crazy battle scenes, sword fights, and one hell of a knighting scene.

13 Henry Morgan

Henry Morgan is probably one of the more recognizable names on this list, thanks to the Captain Morgan brand of rum and references to him throughout pop culture. He conquered several cities in the Caribbean, including Porto Bello in modern day Panama. He was actually arrested during his career, but still managed to find himself the governor of Jamaica. Ironically, Jamaica passed a few anti-piracy laws while Henry Morgan was governor, and he actually prosecuted a few pirates! While he lived and died several hundred years ago, his ship was actually discovered back in 2011.

Taking aside Captain Morgan's rum, Henry Morgan has shown up throughout pop culture. Henry Morgan is actually part of the Pirates of the Caribbean lore, as one of the founders of the legendary Pirate Code, which is actually pretty cool. He's also shown up in a ton of TV shows and literature, so he's definitely sparked some interest with people. He's even the distant relative of two generals that took part in the American Revolution and Civil War, respectively. Even his descendants would make good movies.

12 Pedro Menendez de Aviles

Pedro Menéndez de Aviles was a Spanish pirate (which is interesting considering the last three pirates on this list were targeting the Spanish) who founded St. Augustine, Florida, which is a lovely vacation spot and the oldest city in the continental U.S. Additionally, he was the very first governor of Florida ever, which is pretty cool. On top of that, he was part of the royal party when Philip married Mary I, Queen of England, and he took part in a lot of really cool operations. Here's his own words of how he described sailing from Florida to Havana, Cuba:

"I was wrecked at Cape Canaveral because of a storm which came upon me, and the other boat was lost fifteen leagues further on in the Bahama Channel, in a river they call the Ais, because the cacique (chief) is so called. I, by a miracle reached the fort of St. Augustine with seventeen persons I was taking with me. Three times the Indians gave the order to attack me, and the way I escaped them was by ingenuity and arousing fear in them, telling them that behind me many Spaniards were coming who would slay them if they found them." [Rouse, Irving. Survey of Indian River Archaeology. Yale University Publications in Anthropology 45. ISBN 978-0-404-15668-8.]

That incident alone would make a great movie, and it would be an original one, because Aviles isn't a huge figure in pop culture. However, he really could be, so some filmmaker should really get on it.

11 Blackbeard

Blackbeard was born Edward Teach, and he was one of the biggest figures of the Golden Age of piracy, which is the age that the Pirates of the Caribbean franchise is mostly based off of, not to mention the fact that Blackbeard actually shows up in the fourth installment. He did a lot of big things throughout his career as a pirate, but one of his more famous exploits involves capturing a French slave ship, outfitting it with forty guns, and renaming it the Queen Anne’s Revenge. He then went on to use it to take over the port at Charleston, South Carolina and hold it for a good long while before he was given the chest of medicine that he wanted. He managed to lay low for a few months before getting killed, and according to legend, he was stabbed something like twenty times and shot five times. He was also known to have coiled smoking fuses into his long, braided beard and slung different types of weapons across his chest, so cinematically, he'd definitely look pretty cool.

10 François l'Olonnais

François l'Olonnais was born Jean-David Nau, and was a French pirate active during the 1660s. Technically, he was a buccaneer, much like some of the others on this list, which makes him kind of a cross between a pirate and a soldier, so he was kind of an outlaw sponsored by the French state, much like some of the others were sponsored by their respective countries. He was given the moniker "the bane of Spain" and was the first of only two men to be given that title (the second only got it last year!). He's known for killing his victims in very gruesome, memorable ways. He was also apparently very, very good at the awesome one liner, if his crewmates were anything to go by:

"He drew his cutlass, and with it cut open the breast of one of those poor Spanish, and pulling out his heart with his sacrilegious hands, began to bite and gnaw it with his teeth, like a ravenous wolf, saying to the rest: I will serve you all alike, if you show me not another way".

Now that's a moment for a particularly gruesome trailer. They'd have to clean up some of the imagery, because some of it definitely wouldn't work for a mainstream movie, but you have to admit that this guy would make a great story.

9 Captain Kidd

Captain William Kidd was a Scottish pirate who was originally charged with bringing them to justice before he went rogue. To be fair, some people are convinced that Kidd's pirate reputation wasn't really earned and he was just a privateer, which means that he is either one of the most notorious pirates in history or one of history's most vilified privateers, and we have no real way of knowing which, especially considering that he wasn't as violent or quite as successful as his counterparts. He only took part in a few skirmishes as a pirate/buccaneer, and spent the later parts of his life trying to clear his name, but his life was an interesting one. He's shown up in pop culture before, in two films made before the 1960s and a few video games, among other things, so he's no stranger to any form of media. However, a big movie about him would be interesting, especially given how the filmmakers would interpret exactly what Kidd's role was in history.


8 Sir Walter Raleigh

You might remember Walter Raleigh from your history books as one of the men who helped explore early America, but the man has more depth than that. He was actually a poet, a spy, a courtier, and a ton of other things. Aside from his exploits in the New World, Raleigh sailed to find a City of Gold which contributed largely to the tale of El Dorado, married one of Queen Elizabeth's ladies in waiting in secret and got imprisoned for it, was imprisoned again for his role in the coup against King James I, and was generally one of the most notable figures of the Elizabethan era. Also, he's widely considered to be the person who brought the potato to Europe, so that would be a fun moment to bring to the big screen.

7 Madame Cheng

Madame Cheng was a 19th century pirate who took over for her husband, who managed to build what became the largest pirate confederation in history. At the very height of her powers, she commanded something like an estimated 1,800 ships and 70,000 men, which is bigger than the armies of some modern countries if you really think about it. Together with her husband's adoptive son (who was also her boyfriend), she attacked ships, kidnapped seven British soldiers, and blackmailed coastal communities. On top of that, when the Chinese authorities began to crack down on piracy, she took a pardon and lived out her golden years running an opium smuggling ring. Not only would we have a great movie with a POC female at the helm, we'd have a sequel that would be a cross between The Golden Girls and Breaking Bad. Now, that's something truly watchable.

6 Rafael de Nogales Mendez

Rafael de Nogales Méndez was a 20th century Venezuelan soldier who served under the Ottoman Empire as a major. He was also part of a failed coup, several battles, and even spent some time as a cowboy. Not only was he an incredibly capable man on the battlefield, he was a man with principles: he asked to be relieved of his duties because he didn't want to take part in "the massacres of Christians." On top of that, he was a prolific writer who wrote several books that documented many of his experiences fighting in several wars, including World War I:

"At dawn I was awakened by the noise of shots and volleys. The Armenians had attacked the town. Immediately I mounted my horse and, followed by some armed men, went to see what was happening. Judge of my amazement to discover that the aggressors had not been the Armenians, after all, but the civil authorities themselves! Supported by the Kurds and the rabble of the vicinity, they were attacking and sacking the Armenian quarter, I succeeded at last, without serious accident, in approaching the Beledie reis of the town, who was directing the orgy; whereupon I ordered him to stop the massacre. He astounded me by replying that he was doing nothing more than carry out an unequivocal order emanating from the Governor-General of the province to exterminate all Armenian males of twelve years of age and over." [Lee, Rafael de Nogales; translated from the Spanish by Muna (2003). Four years beneath the crescent. London: Sterndale Classics. ISBN 1903656192.]

Given all of the source material that comes right from the source, there would be a ton of material to make a movie out of.

5 Calico Jack

Calico Jack was born John "Jack" Rackham, and he's famous for two things: the Jolly Roger flag and his two female crewmates, Mary Read and Anne Bonny, who we'll be talking about a little later. He had a short but legendary run as a pirate before he was captured by the governor who'd pardoned him and his crew before, and was hanged the following month. Among his exploits are: escaping capture by abandoning his old ship and sailing away on his new ship with his crew and capturing a ship with a huge treasure aboard within sight of the Port Royal shore. This isn't even getting into his interesting relationship with Anne Bonny and the lives of his crewmates.

The life of Calico Jack would make an incredible pirate ensemble movie, where everyone gets their own day in the sun. He's already a character on Black Sails and he shows up in Assassin's Creed IV: Black Flag, so a major movie franchise would really work for him.

4 Napster

You might be surprised to find Napster on a list about classic pirates, but there's probably no better example of piracy in the modern age than Napster, the company founded by Shawn Fanning, John Fanning and Sean Parker. You might remember the last name from the movie The Social Network, where he was played by Justin Timberlake. Back before the age of streaming, Napster was the pioneering site for peer to peer sharing music (P2P), not only because the technology behind it was user friendly (this was at the advent of the MP3, when programs like this weren't so friendly), but because up until that point, no one had ever shared music this way and on this scale. It's a music store under Rhapsody now, but in its original incarnation, Napster was the program that would be the father of such programs like Bearshare, Limewire, Kazaa and edonkey 2000, which is an actual name for a P2P sharing program that I didn't know about until now. Needless to say, there was a lawsuit which made the law catch up to the technology, and Napster went bankrupt. However, the name of the company remained, and it ended up becoming what it is now.

There won't be any swordfights in this movie, but a movie about Napster would be as good as or better than The Social Network.

3 Anne Bonny


We've talked a little bit about Anne Bonny earlier, but as a female pirate whose life is shrouded in mystery, she deserves special mention. She was born Anne McCormack in Ireland, to a merchant father and his serving girl. Her father built his fortune in London and eventually married her off to James Bonny, a small town pirate and merchant. They then moved to Nassau, where James Bonny became an informant and Anne met Calico Jack, with whom she had a son in Cuba. The couple, after Anne divorced and married Calico Jack at sea, built a crew with Mary Read (who actually spent some time as a pirate dressed as a man) and captured ships all around Jamaica.

While she never captained a ship of her own, she was historically renowned as a great fighter and pirate and as a person that her crew respected. She and Mary Read were among the few to fight when they were captured, and escaped execution by "pleading their bellies" which gave them a stay of execution thanks to their pregnancies. While Mary Read died in prison due to complications after the birth, Anne Bonny simply disappeared. According to the evidence, she either went back to piracy under an assumed name or went on to marry a nobleman, change her name to Annabelle and have eight children before dying of old age.

Regardless of how her story ended, her story is an interesting one. She's kind of the Black Widow of this list: she'd do great as part of an ensemble story about Calico Jack, but her story stands on its own and could be its own movie in its own right.

2 Demetrious of Pharos

Demetrius of Pharos' story takes place long before the stories of anyone else on this list, so the swashbuckling stuff is completely absent. Born two hundred some odd years before Christ and over a millennia before the Jolly Roger, Demetrius of Pharos was a client king for the Romans before defecting to the Macedonians and eventually becoming an advisor to King Philip V of Macedon and playing him like a fiddle. One of his advisors puts it like this:

"For Demetrius was so assiduous in keeping hot these hopes and projects in the king's mind, that Philip even dreamed of them in his sleep, and thought of nothing else but this Italian expedition. The motive of Demetrius in so acting was not a consideration for Philip, for he certainly did not rank higher than third in the calculations of Demetrius."

Basically, this guy is like a cross between Davos Seaworth and Littlefinger, guys. He had the military chops to conquer cities and lay fleets to waste, but also had the political acumen to get himself to where he needed to be. In Demetrius's own words:

"If you have the heart of an augur, to quit it as quick as you can: but if of a gallant and wise king, to keep it, lest if you quit it now you may never have so good an opportunity again, for it is by thus holding the two horns that you can alone keep the ox under your control"

Now, if this guy's story wouldn't make a great movie, I'll eat my hat. It would probably have so many cool quotes in it, just because of the setting and who Demetrius was as a person.

1 Roberto Cofresi

Roberto Cofresí y Ramírez de Arellano was a Puerto Rican pirate who rose from humble beginnings to to create a network of informants and associates that was so strong, it wasn't fully dissolved until fourteen years after his death. He wasn't just a great pirate and privateer, he was the greatest one of his time. He has been credited with something like seventy captures and eight ships taken, and evaded capture by vessels from six countries, including the United States. He was never actually charged with murder, but his exploits probably caused the deaths of something like three hundred people, and his unique personality made it so local authorities were flummoxed by him and needed help from international forces to capture him. He didn't impose a pirate code upon his men, which was unique for a pirate at that point. He was executed in 1825, but his legacy continued long after his death, and his legacy is taken as facts in Puerto Rico and the West Indies.

As a Puerto Rican and as a human who loves movies, Roberto Cofresi would make an incredible movie. Spanish authorities tried to make him look like a villain, but they actually made him look like a legend, and the image of a romanticized, swashbuckling pirate comes from him. There have been a few attempts to immortalize him on film, but this guy deserves a little more than that: he deserves a blockbuster. That means some amazing filmmaker has to get on it!


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