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Top 10 – Menacing Pirates

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A life of freedom upon the open sea is a dream for some, but it is not a vocation without perils. Out there where men are free, they can be free of oppression, taxation, and the rule of land, to pursue whatever desires of conquest and greed they please, so long as they’re happy to also be at the mercy of others who want to do much the same thing.

Here we have assembled a gathering of the most terrible captains, wicked crews and vicious looters, pillagers and ravagers known to these seas or any others. Mutinous scoundrels of history and fantasy, gathered one and all in this week’s Top 10.

Top 10

10) The Crimson Permanent Assurance – Monty Python

Above is the entire saga of The Crimson Permanent Assurance, but for those of you unwilling to watch the full quarter hour, here’s the summary – as a prologue to the general mismatched and utterly irrelevant content of Meaning of Life, The Monty Python gang tell us the story of an ancient accountancy firm who take to a life of piracy, setting sail in a corner building to lay waste to modern firms.

For a bunch of old men who’ve put their gear together out of stationary and sharpened ceiling fan blades they look pretty vicious, and they really do stick it to the scumbags in their italian knock-off suits! And as all pirates must they can carry one hell of a tune too.

9) Brook – One Piece


I won’t lie, One Piece has many more fearsome pirates in their midsts. We’ve probably picked a lot of characters based on their actions, as well as their appearance, but for this particular example, we decided to go for Brook of One Piece. He might not be the best choice from the series, but his looks are pretty menacing.

We picked him purely on the aesthetics of a nine-foot skeleton coming at you. He’s also one of the pirates that uses the powers of the Devil Fruit, a gift from the Sea Devil himself. It’s no wonder that Brook, as outlandish his outfit is (after all, he is a musician), has such a terrifying look about him. Imagine seeing a skeletal pirate coming at you? Yeah, I’d be pretty scared too.

8) Captain James Hook – Hook


It’s hard to call Captain James Hook menacing per se, unless you look at the alternate designs of Dustin Hoffman. The Captain is well known for being a scoundrel of the seven seas, as well as having a strange infatuation with making one little boy’s life a living hell. But why, oh why, is this grown up pirate so obsessed with his hatred for Peter Pan? This is a question that can only be explained through backstory.

To give you an idea, he and Pan were indeed friends. However, a fateful incident saw Hook, who was just an adventurer at this time, lose his hand. This is what made Hook go from a simple adventurer to the all out scourge of the seven seas, Captain James Hook. Hatred fills this pirates heart, pure unadulterated hatred for the one who caused him to lose his hand to that terrible crocodile, Peter Pan and the lost boys. They say hate is a powerful emotion when it’s targetted, the captain isn’t afraid to kill, like in a very dramatic scene in Stephen Spielberg’s Hook.

7) Bloodsail Buccaneers – World of Warcraft

Bloodsail Buccaneers

The Bloodsail Buccaneers aren’t exactly the most prolific bunch of characters in World of Warcraft, but they have been there since the very beginning and they are the mortal enemies of Booty Bay. Sure, they may be relatively low level mobs, but they do have some good tactics, as well as being one of the only remaining pirate tropes in the world of Azeroth.

Whilst they may never rise to the top of the list of threats in the World of Warcraft, they do look pretty menacing, standing around with their guns and swords, ready to strike. They loiter in places which just reeks of ambush and are actually overall a pretty cool faction to get into. If you manage to get exalted by them, you get your very own parrot companion and pirate hat. For a bunch of scary pirates, these guys don’t seem so bad after all… So why do they hate Booty Bay? They don’t really: They just want to plunder Booty Bay and the Steamwheedle Cartel.

6) Barbossa – Pirates of the Caribbean


Formerly dreaded, then undead, then not dead at all, truth be told Hector Barbossa has been all manor of pirate in his time, from captain of a ghost ship to bootlick to his majesty’s royal navy, he has a particular talent for not only adapting to the changing tides but excelling in in them too.

Now don’t get us wrong, Jack Sparrow is just as talented at surviving in a world that very clearly wants him dead, but we are looking for menacing pirates here, and Sparrow is not exactly menacing, just very… very… savvy. Captain Barbossa has the gravitas, the reputation, and the ruthless cunning to really build a reputation deserving of fear, and a name to strike terror across the seas, a real captain, not just a clown with a talent for getting lucky.

And now he’s got a ship that he can control by means of waving a sword around, there was some serious chills when those sails filled, but whether it’s the Black Pearl or The Queen Anne’s Revenge, he’s always a daunting nemesis, and a debatable ally.

5) Ghost Pirate LeChuck – Monkey Island


On first inspection, the Ghost Pirate LeChuck might be one of the most menacing pirates to have ever graced video games. He’s a ghost pirate, which is a pretty scary start if you ask me, but then couple that with his appearance changes later in the games, such as his massive flaming beard, you’ve gotten yourself an undead pirate who wants nothing more than to take Elaine Marley’s hand in marriage. Oh wait, that’s not such a menacing thing…

LeChuck’s strengths are his command over the undead, of which you go to combat occasionally. But it’s through his strengths that he’s arrogant and cocky, which also means he’s pretty funny. For such a scary looking guy, his plans are generally just half-baked. They seem to have no real substance, but hey, he looks scary in the process. He can even throw a fireball at… your… feet… Okay, why not at the body? Does this guy even know how to pirate properly?

4) Dark Eldar – Warhammer 40,000


The hedonistic counterparts of the more cerebral Eldar, a band of nomadic outcasts taken to reaving, pillaging, enslaving and generally getting away with whatever they please. They also inadvertently gave birth to a god of chaos and almost wiped out their own species, but that’s no reason not to enjoy yourself. The Kabals of Commorragh sweep out of the warp in droves with their highly advanced raiding vessels that strongly resemble ships at full sail and descend upon the weak and vulnerable.

That may be why they’re no good on the table, because none of the 40K armies can be called weak and vulnerable. If you could play a game where you can commit your forces to strangle supply lines, enslave civilian populations and lead wars of attrition against stronger military forces then the Dark Eldar would be flawless.

Heavy duty monsters, terrifying beasts and a variety of mutant creations of advanced sciences indistinguishable from magic complete the crew, because what makes for a more effective pirate than one with wings or a bunch of extra limbs? How about Hobgoblin-style gliders, witches and battlefield surgeons? Well, they carry surgical gear anyway…

3) Dread Pirate Roberts – The Princess Bride


Feared world over as a ruthless bandit of the seas, a wicked swordfighter, and not known for his merciful treatment of prisoners, or for taking them at all. Like Barbossa, Roberts is an immortal of sorts, a figure of almost mythological terror who’s name echoes with fear, and slips into the very nightmares of even the most stalwart of souls. Also, interestingly, doesn’t exist.

Turns out a black mask, a solid bit of training and someone to call you Captain Roberts around the crew is all you need to assume the role, usually best to take the former Dread Pirate Roberts to take up the job of first mate to really sell it.  Name and reputation get passed along from Roberts to Roberts as each man makes enough money to retire to an Island somewhere in Patagonia. The name itself sparks enough terror that with the right theatricality then you can use the name to conjure the spectre of death, enough to terrify an army into submission.

2) Ironborn – Game of Thrones


“We are Ironborn. We’re not subjects, we’re not slaves. We do not plow the field or toil in the mine. We take what is ours.”

It’s in the very words of the family Greyjoy, “We do not sow”, the children of the Iron Islands are born to work hard at stealing from everyone within reach, and given that the islanders craft the finest vessels in Westeros there’s not an awful lot outside of their reach except things too far inland. You may recall the foolish attempts of Theon to take Winterfell and the rest of the north, dooming him and his men to a rather bleak fate.

The Krakens worship the Drowned God, hardly a strict religion, one that actively encourages a wide variety of crimes, all in the name of paying the Iron Price for what they want and need, a price in blood and steel rather than gold and trade. It’s one hell of a cultural attitude that has caused them to be thrown back into the sea by a variety of rulers the world over, still they persevere, and many names live on in terrible legend amongst the Ironborn.

Also, here’s an interesting fan theory that may well prove to be a spoiler for fans of the books and TV series.

1) Edward Teach – History

Edward Teach

Were we somewhat biased in what we decided was the most menacing pirate of all time? You bet’cha, it’s none other than Bristol’s very own Edward Teach, the man that so many people remember, as the most infamous pirate of all: Blackbeard. Yes, he’s a Bristolian, born and raised and y’know what? Here’s a little history lesson for all who care to indulge for a few minutes!

Blackbeard was a terror of the seven seas, but for the most part, his deeds were somewhat exaggerated. This may be because those who were met with encountering him generally were fearful of him. During combat, he’d put fuses in his beard and light them, giving the effect that he had a smoking aura about him. Some people, especially enemy pirates at the time, would have thought of him to be a sea devil.

They say that when he was eventually killed, he had taken no fewer than five bullets and twenty slashes. That’s definitely the fighting spirit a pirate should possess – but coupled with his general size and his smoky appearance, Blackbeard might be the most terrifying pirate to have ever graced the seas. Yo ho ho, cap’n!


Honourable Mentions

Our rogue’s gallery is almost complete, and while we’ve already settled on public enemy number one, there are still plenty of criminals on the waves to consider, whose names echo throughout history and fiction alike. So before ye disembark, have a gander at yon ruffians still unaccounted for.

Jessie and James of Team Rocket – Pokemon


I bet you’re now scratching your heads and wondering why on Earth we would put Team Rocket in a list of menacing pirates. Well, you may be surprised, but when you consider what Team Rocket do, they actually are akin to pirates. They don’t sail the seven seas, but instead, they’re what we like to call a Sky Pirate. These kinds of pirates fly around in blimps, or hot air balloons and strike from above, when their opponents are least expecting it.

You’d be forgiven for thinking that they couldn’t ever be menacing either, but that couldn’t be further from the truth. Whilst they are blundering idiots, who lose to an even bigger blundering idiot in Ash Ketchum, the fact they are so brash that they are able to come down from the sky in their massive, very undisguised hot air balloon, have their own theme song and be part of what is considerably one of the most influential criminal syndicates in the land of Kanto, Jessie and James don’t need big beards, stacks of loot and treasure chests to be pretty cool pirates. Now, hand over your Pikachu!

Long John Silver – Muppets Treasure Island

The cook serving under Captain Smollett on the Hispaniola is a famous traitor and mutineer whose name is synonymous with piracy. And yes, he’s ruthless, and yes he’s terrifying enough on his own, although clearly not quite enough to make the list, I’d much rather face off against one peg-leg and his parrot than a band of roving accountants. But when that pirate is portrayed by the full-voiced legend Tim Curry? And commanding a band of murderous muppets no less, then Long John Silver is most certainly deserving of mention.

Much like our number one slot, Silver’s also a Bristolian, albeit a fictional one. Little else need be said, just listen to the song and know that we’re right.


Once again, we cast off and make for the horizon, leaving the shores we know for new and hitherto unexplored Top 10 lists, a life of adventure, and you can help set the course. Have your say, join the conversation, and vote for next week’s list. If you don’t vote then you only commit your pick to Davy Jones Locker*.

How did we do this week? Did your favourites make the cut? Weigh in with your say in the comments below, or on our Facebook and Twitter pages.

*And yes, Davy Jones was considered.


6 responses

  1. Murray

    “That may be why they’re no good on the table”
    Look, the Fall of the Eldar hit us hard, we only have paper mache and duct tape to put our vehicles together. Sure they have a tendency to explode violently and cause a chain reaction of death among everyone, but we make do!
    In the right hands we’re deadly though :3

    Great list as always! <3

    Liked by 1 person

    February 20, 2016 at 1:40 pm

  2. No one rocks as hard as Blackbeard. Funnily enough he was one of the nicer pieates. If you surrendered he’d leave you enough supplies to make it to the nearest port. Things only got deadly if you got stupid.

    Liked by 1 person

    February 20, 2016 at 1:47 pm

    • Most pirates believed in being relatively peaceful, contrary to popular opinion. You’re right: He would leave you alone if you caused no problems…

      The fun fact is pirates used to get hired by kings and queens, as well as governments. They were used in over seas missions. Pretty cool fact :)

      Liked by 1 person

      February 21, 2016 at 9:35 am

      • Privateer was the name :)


        February 21, 2016 at 9:39 am

      • Nope: Not quite! They went to get pardons before that. A pirate became infamous, got summoned by their king/queen and acted like a mercenary. It cost, but it was damn effective.

        Liked by 1 person

        February 21, 2016 at 9:41 am

      • Captain Hornigold was one of the more famous pardoned pirates. He then went on to become a “Pirate Hunter,” taking out his former comrades.

        The “Golden Age of Piracy” is a fascinating era


        February 21, 2016 at 9:50 am

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