Pirates are always a good decision. It sounds like a trite thing to say, but it’s true; pirates, whether they’re heroes, villains, or somewhere in between, are perfect characters for adventure, mystery, fighting the powerful, serious ruminations on social and economic hierarchies, you name it. They rely on their own abilities and create their own fates. They aren’t always helpful, but they’re never boring. With that in mind, we’ve amassed a list of some of our favorite fantastical scalawags and the books they come from. Heave to it, and check them out!
Captain Hook (Peter Pan by J.M. Barrie)
It’s a cliché for sure, but it’s hard not to love Peter’s greatest foe, Captain James Hook. Peter Pan’s status as a beloved children’s classic means that there are so many iterations to choose from, so you’re bound to find a Hook that fit your particular needs. Whether you love the classic villain of Barrie’s book (and play), the foppish glee of the musical, the needy petulance of the captain in his own eponymous film, or the smolder of Once Upon a Time’s rogue, Captain Hook is always here for you, and there’s no right version because all are equally valid. Okay, we might give a bit of a leg up to Jason Isaacs from the 2003 film. He’s fabulous.
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Peter Pan
Teriana (Dark Shores by Danielle L. Jensen)
This YA adventure takes place in a world where there are a special class of people who navigate the seas called the Maarin. Heir to their Triumvirate is Teriana, the second mate of a ship called the Quincense, paired with a solider of the Celendor Empire named Marcus on a journey to conquer a place called the Dark Shores. It sounds daring and exciting, sure, but when you’re a pirate matched up with a guy holding onto a secret, and you’re being asked to use your ship and crew for an impossible quest that force you to break the rules of your people… well, it’s not great. Teriana is still up to the task though, and seeing as this is book one of a series, she’s got a long way to go and many more adventures to unpack.
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Dark Shores
Captain Shakespeare (Stardust by Neil Gaiman)
In the book, Tristran Thorne and the star Yvaine accidentally get themselves stuck in sky when they try to travel by candle, and wander among the clouds for a bit before stumbling upon a sky pirate and his crew. This interlude in the story is wonderful, but these particular pirates were given even more to chew on in the 2007 film version of Stardust, which named the head pirate Captain Shakespeare and saw him played by none other than Robert De Niro. Shakespeare is obviously a queer man in this version, and he has a wonderful time confiding in Tristan and Yvaine about the closet full of luxurious dresses and makeup that he keeps on board. Later he finds out that he crew knows all about his alter ego, and they still love him dearly. Supportive pirate crews FTW, y’all.
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Stardust
Li (The Pirate Empress by Deborah Cannon)
A pirate of circumstance, Cannon’s protagonist Li is actually a princess during China’s Ming Dynasty with a prophecy attached to her name—one that declares she will bear the Son of Heaven, a future emperor. Li has to leave her home after her son is kidnapped, and without help from her grandfather (who’s a warlock) or her lover, she finds herself forced into marriage with a pirate admiral. She has to learn quickly in order to ensure her survival in the hopes that she will find her son, and also defeat the Fox Faerie, a being with magic so corrupt and terrible, it threatens human civilization as we know it. This story showcases the darker side of pirate life, but if you’re intrigued by Chinese mythology and history, you’re sure to love Li’s journey.
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The Pirate Empress
Devyl Bane (Deadmen Walking by Sherrilyn Kenyon)
In the 1980s and ’90s, Sherrilyn Kenyon wrote pirate romances like A Pirate of Her Own under the name Kinley MacGregor. And as the descendant of historical pirate Jonathan Barnet—who apprehended Anne Bonny, among other famous swashbucklers—she has a personal investment in these stories. So when she returned to that world for the Deadman’s Cross series, readers rejoiced—especially when she threw fan favorite Thorn into the fray. The immortal Hellchaser strikes up an uneasy partnership with Devyl Bane, a warlord brought back to the human realm as a pirate on the Spanish Main, in order to push back demons threatening to break down the gates between worlds. Thorn, Bane, and their crew of Deadmen must sail on the Sea Witch—a ship, but also a woman with her own personal stakes in this conflict—to try and save humanity.
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Deadmen Walking
Rolfe (The Assassin’s Blade by Sarah J. Maas)
Like all good pirates, Rolfe receives his title (of Pirate Lord of Skull’s Bay) through a shaky bargain—in his case, the intervention of the Sea God, a magical map inked onto his palms, and the loss of all that he holds dear. But when he meets assassins Celaena Sardothien and Sam Cortland in the Throne of Glass novella The Assassin and the Pirate Lord, Rolfe is the one setting the negotiations. Led as much by his pragmatism as by a compass, the Lord of Ilium (as he is also known) will make questionably ethical choices when it comes to wiping out his enemies. But he is no monster, and will go to great lengths to save others from suffering bad fortunes like the one that first made him Pirate Lord.
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The Assassin's Blade
Kazan Atrabiades (Kushiel’s Chosen by Jacqueline Carey)
While Phèdre nó Delaunay gets swept up in a frustratingly long side-quest in the second Kushiel novel, she could do worse when it comes to adventuring companions. Illyrian pirate Kazan rescues the anguisette after she escapes the island fortress of La Dolorosa, but instead of taking her straight to her allies, he brings his beautiful and intriguing hostage along on his own quest for redemption. Cursed by his own mother with a blood-guilt due to accidentally murdering his brother in battle, Kazan is stalked by the fiery-eyed kríavbhog, forbidden from returning home until he has ritualistically cleansed his soul in the thetalos ceremony. While Kazan initially comes across as little more than a rogue, demanding Phèdre’s particular skills as a Servant of Naamah in exchange for his help, during their voyage he slowly opens up. By the time they part, he has proven himself a brave, surprisingly sensitive man who has come to respect her as more than a body, more than a bargaining chip, even eventually apologizing for their imbalanced arrangement.
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Kushiel's Chosen
Sim (The Lady’s Guide to Petticoats and Piracy by Mackenzi Lee)
Facing down the prospect of a stultifying marriage that will forever dash her dreams of becoming a doctor, Felicity Montague makes a last-ditch attempt to attain her dream: become the research assistant to an eccentric physician who happens to be marrying her estranged best friend. But the wedding is taking place in Germany, and Felicity has no way of getting there from London… until a mysterious young woman offers to finance her voyage, if Felicity will let her tag along pretending to be her maid. This odd request is Felicity’s first dealing with sword-wielding Algerian Muslim pirate Simmaa “Sim” Aldajah—but as they take to the high seas and Sim’s true intentions begin to surface, Felicity gets swept along in the kind of high-stakes adventure she never could have imagined. Once runaway bride Johanna Hoffman enters into the story, this trio makes for compelling leads with their own unique dynamics, from Felicity and Johanna’s adolescent strife to Sim’s attraction to Felicity tempered by their clashes over colonialism. While Johanna and Felicity each grapple with their identities with regard to attraction and societal norms of femininity, Sim must prove that she deserves her birthright, to inherit her father’s fleet of pirate ships.
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The Lady's Guide to Petticoats and Piracy
Lila Bard (A Darker Shade of Magic by V.E. Schwab)
When we meet Delilah Bard in A Darker Shade of Magic, she hasn’t actually made it as a pirate just yet. It’s more of a longterm goal, one that she’s working toward by picking pockets and living on a docked old boat that will likely never sail again. (It’s just as well, as said boat later goes up in flames.) Lila’s luck changes when she meets a young man named Kell who heralds from Red London, an alternate universe of sorts where magic is everywhere. Lila follows him through to that world and quickly gets herself a job as a thief on a ship called the Night Spire, deposing the thief who came before her. Lila’s ambition takes her everywhere fast, though, and it’s not long before the Night Spire is hers. She contributes far more to the story than her thieving prowess and desire to sail the seas, but Lila’s pirate aspirations are a part of her wanderlust and charms.
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A Darker Shade of Magic
Zamira Drakasha (Red Seas Under Red Skies by Scott Lynch)
Scott Lynch’s Gentleman Bastard series is full of glorious crooks and swindlers and liberators of wealth, but it isn’t until the second book that we get to meet a genuine swashbuckler who makes us swoon. Zamira Drakasha is the pirate queen of all our hearts, member of the Council of Pirate Captains and commander of a ship called the Poison Orchid. She is the sort of pirate one rarely sees in fiction: she’s a mother of two, two toddlers to be precise, named Paolo and Cossetta. She’s also in her forties, another rarity on the adventuring front for women. Imagine being a good enough pirate that you could keep your children on your pirate ship and just let them hang around while you plundered and otherwise owned the seas. Imagine being a boss like Zamira Drakasha.
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Red Seas Under Red Skies
The Piracy (The Nature of a Pirate by A.M. Dellamonica)
The pirates on this list are, for the most part, positive figures; their struggles inspire sympathy, even if we disagree with their general looting and plundering. It’s more difficult to make that case for the Piracy, the central villains of A.M. Dellamonica’s Stormwrack series. As antagonists, they are incredibly fitting for the waterlogged world of Stormwrack, made up of island nations literally struggling to stay afloat and a central governing body containing hundreds of ships always moving with the tide. For the first two books, the Piracy are clearly the bad guys, attacking the Fleet of Nations in its weakest spots in order to physically and figuratively break up its shaky peace. But that’s not how the pirates see it: Dellamonica wrote a compelling essay reframing piracy as a cultural construct, what began with five island nations going rogue but has grown into a way of life. “How do you dress, think, feel, and talk if you’re a pirate who can’t openly practice piracy?” she asks. “As a defeated nation with a bloody reputation, what do you teach your sons and daughters about the past?” While the Stormwrack series is mostly from the perspective of a young woman from Earth and her fellow crew on the Nightjar, the final installment of the trilogy ponders survival on the seas from all sides.
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The Nature of a Pirate
Who are your favorite buccaneers in fantasy?
