Top Ten Fictional Pirates

Avast, matey! Talk Like a Pirate Day be coming up, so pull up a barrel and help yerself to some grog as I be running through a list of my favourite fictional pirates!

Pirates are characters that lend themselves to a fantasy setting really well. Even those pirate tales that couldn’t strictly be called fantasy tend to feature fantasy elements, such as curses, ghosts and zombies (either literally or as stories whispered in foggy lantern light). Stories of adventure, swashbuckling, treasure-hunting and exploring strange lands also go hand in hand with the pirate world. Pirates can be a bit of cheesy fun, or gritty and grim, and every shade in between…

So, on to the list. Arrrrr!

Captain Hook

(Peter Pan by J M Barrie, Peter Pan movies, Once Upon a Time, Hook)

I didn’t want the headache of trying to rank this lot in order of preference, but if I had, then Captain Hook would’ve topped my list. Hook is a pirate who knows how to villain in style, whether it’s the large hat with floppy feather, luscious perm, buckled shoes and lace cuffs; or the good looks and charm of Killian Jones.

Hook doesn’t waste time pursuing the petty rewards of looting merchant vessels and burying treasure on forgotten islands, which other lesser pirates seem to concern themselves with. No, he follows a higher calling – to rid Neverland of a small boy in green tights. Capturing members of local royalty, interrogating fairies, eluding ticking aquatic reptiles and making children walk the plank are all in a day’s work for him. And he still has time to wax his moustache. What a guy.

Guybrush Threepwood

(Monkey Island video games)

A pirate he was meant to be, trim the sails and roam the sea!

Where do I begin with Guybrush Threepwood? Not only did he defeat the great swordmaster of Melee Island and woo the magnificent Governor Marley, but he also gathered together a ragtag crew, thwarted the dreaded ghost pirate Le Chuck, found the buried treasure of Melee Island (and all he got for it was this lousy t-shirt), AND discovered the legendary treasure of Big Whoop. Oh, and he can hold his breath for ten minutes! He might just be the greatest pirate ever.

The Dread Pirate Roberts

(The Princess Bride by William Goldman, The Princess Bride movie)

Famous and feared across the seas for his ruthlessness in taking no prisoners, his reputation is so strong that ships instantly surrender to him (slightly shaky logic there?).

More a title than any specific person – the position is passed on when the current Roberts is ready to retire – but the particular Roberts we love is one farmboy turned badass, with eyes like the sea after a storm. A brilliant swordfighter, quick-witted and loyal, he’s the pirate you want on your side.

Captain Darian Frey (and the crew of the Ketty Jay)

(Tales of the Ketty Jay series, by Chris Wooding)

Pirate credentials: airship battles, boarding and plundering, hanging out in pirate backwaters, hunting for treasure, stealing treasure, attempting to remove curse from stolen treasure, pistol fights, duelling with a daemon-enthralled rapier, and managing a very angry ship’s cat. Success rate of the above listed piratical activities: embarrassing. This crew might be the most inept at actually being pirates out of everyone on my list, but they have a lot of heart, or at least, they’ve imbibed a lot of alcohol and have nowhere better to go. Who doesn’t like rooting for the underdogs?

Long John Silver

(Treasure Island by Robert Louis Stevenson, Treasure Island movies, Muppets Treasure Island, Treasure Planet, Black Sails)

Long John Silver is the guy who set many of our pirate expectations, not to mention Halloween costumes – the peg leg and the parrot on the shoulder, his crafty and clever ways, and his pragmatically shifting loyalties… but a likeable rascal nonetheless. He’s obsessed with finding his share of Captain Flint’s treasure and claims to be the only man Flint ever feared. Other versions present him as a cyborg (Treasure Planet) or explore his earlier years (Black Sails – a John Silver and Flint origin story, amongst other things). John Silver is one of those pirates, like Hook, who we never seem to tire of.

Captain Zamira Drakasha

(Red Seas Under Red Skies, by Scott Lynch)

Captain of the Poison Orchid, Drakasha is a member of the Pirate Council of Port Prodigal, infamous across the Sea of Brass, a skilled fighter and total badass, a single mother who comes home to her ship to hug her toddlers after a day of looting and pillaging.

She’s loyal, clever and extremely capable, a good captain and a good mother.

Oh, and you’d better not sit at her table without permission, because this woman knows how to make a point.

Captain Trinica Dracken

(Tales of the Ketty Jay series, by Chris Wooding)

Yep, another Ketty Jay entry – this series would be my number one recommendation for fantasy pirate books. Dracken, Captain of the Delirium Trigger, is both antagonist and occasional ally to the Ketty Jay crew, due to the friction/attraction between the two captains and their joint past. She’s just as likely to help them one day as stab them in the back the next. Dressed all in black, painted in ghoul makeup with all-black contact lenses, Trinica uses her frightening appearance, fearsome reputation and a cold, ruthless attitude to inspire fear and hold her crew in a firm grip.

Captain Jack Sparrow

(Pirates of the Caribbean series)

It’s never easy to tell with Jack Sparrow whether he’s very clever or just very lucky, if he’s loyal or completely self-centered.

Chaotic good? Perhaps just chaotic.

Bumbling and befuddling, seemingly in a state of perma-drunkeness, he nevertheless somehow always manages to come out on top.

Isabela

(Dragon Age 2, Dragon Age Origins)

Does Isabela have a last name? I can’t remember ever finding it out.

Anyway, Isabela is captain of the Siren’s Call, a famous pirate of the Eastern Seas and an expert duellist. We first meet her in Dragon Age Origins but she becomes a true companion in the second game, as well as a potential love interest. Charming, funny and devious, she believes in freedom and disapproves of authority. Isabela is a capable and entertaining, if perhaps not entirely trustworthy, member of the team.

Jack Rackham and Anne Bonny

(Black Sails)

I know I said this was a list of fictional pirates, so technically these two shouldn’t be here. But, since they appear on TV series Black Sails, which features both real and fictional pirates together with some entirely made up events, I count these versions of them as fictional. Besides, are we really going to argue about rules in an article about pirates?

These two are a team, no matter what – a crew of two even if they have no-one else. Jack is the thinker, the plotter, and much like other pirates on the list he seems to be able to get himself out of any situation. Anne Bonny is the fighter of the pair, skilled and capable, and certainly more hot-headed. While other pirates in the series constantly face off with each other, trying to prove whose gun is the biggest, these two slip around quietly in the background, sometimes down on their luck and sometimes on the up, but it’s clear that they’re a pair to be reckoned with.

Honourable mentions go to: the ghost pirate Le Chuck (Monkey Island games), Captain Flint (Treasure Island, Black Sails), Captain Shakespeare (Stardust movie), many of the Black Sails characters, and Robin Hood (land pirate!). Also a shout out to smugglers (who I can’t help but think of as related to pirates): Davos (A Song of Ice and Fire), Han Solo (Star Wars), and the crew of Serenity (Firefly).

Who are your favourite fictional pirates? Let us know in the comments!

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