Chart a Course to the Best Pirate Stories in Pop Culture

This article covers the best pirate stories in pop culture, including TV, books, movies, and more.

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Ahoy, mateys! If you’ve found this article, you love all things pirates: high-seas adventures, swashbuckling, sword-fights, and buried treasure. Or, perhaps, you’re just making your way into the world of peg legs and ruffled shirts. Maybe you’re coming from your love of K-pop songs like “Pirate King” by ATEEZ, or the musical Pirates of Penzance. Potentially, you’ve just read the 1883 classic Treasure Island by Robert Louis Stevenson and need more parrots on shoulders, eye patches, and anti-English sentiments.

Well, X certainly marks the spot. Below, find the best pirate movies, television series, comics, and even more books. Aye, with release dates as early as the 1960s and as modern as the 2020s, there’s something for every fan. So, what say you? Are you coming aboard? Don’t mind all the gold coins on the deck…

The 10 best pirate stories:

• Pirates of the Caribbean
• Hook
• Muppet Treasure Island
• One Piece
• The Liveship Traders Trilogy
• Treasure Planet
• Firefly and Serenity
• Black Sails
• Princeless: Raven the Pirate Princess
• Our Flag Means Death

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Pirates of the Caribbean

• Released: 1967 (theme park attraction), 2003 – 2017 (movies)
• Features: absurd comedy, curses, and mythology

Yo-ho! Disneyland’s Pirates of the Caribbean attraction in Anaheim, California features narratives about the pirates of the West Indies. Set in the 17th and 18th centuries, the “dark ride” shows these pirates’ various exploits and turmoils as they hunt for treasure. Their voyages, alongside the song “A Pirate’s Life For Me,” became the basis for the Pirates of the Caribbean film series. Most notably, Jack Sparrow leads the five-film Disney franchise. His interactions with key-carrying jail dogs, the cursed Captain Hector Barbossa, and Elizabeth and Will Turner have been incorporated into later versions of the ride in Tokyo, Paris, and Shanghai.

The Curse of the Black Pearl, Dead Man’s Chest, At World’s End, On Stranger Tides, and Dead Men Tell No Tales are fun romps into less-accurate, yet still exceptionally entertaining, horror and pirate lore. These movies include fantasy elements such as ancient curses and sea monsters. Fans also adore the electric tension between Elizabeth and Will, and their sweeping, swoon-worthy romance. But Jack’s antics are the main draw, appealing to viewers of all ages.

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Hook

• Released: 1991
• Features: commentary on escapism and dreams, fun hats and mustaches

Peter Pan, the Lost Boy, is depicted as forever young and free. But what happens when Peter grows up? Robin Williams — the actor of a generation — gives an astoundingly nuanced performance as an adult Peter who has forgotten his dreams and lives a quiet life with Wendy Darling. Stifled and woebegone, Peter longs for another adventure. But he’s forgotten how to find Neverland, or how to use his imagination. Thankfully, Tinkerbell and Rufio’s not-so-gentle reminders might do the trick.

Hook is a gorgeous and somewhat tragic exploration of lost creativity and unrealized potential. Peter Pan always feared not the act of aging itself, but the concept of losing the opportunity to have fun. When propriety and responsibility oppress us, how can we actually enjoy being alive? Inspiring viewers to defeat the singular idea of what it means to be an adult, Hook is a must-watch for anyone who craves an escape from the mundane.

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Muppet Treasure Island

• Released: 1996
• Features: Captain Kermit, colorful crews

Muppets make everything better. That’s just a fact. Muppets Treasure Island puts a puppet-packed spin on the original tale by giving orphan Jim Hawkins muppet roommates. Gonzo, Rizzo, Fozzie Bear, Beaker, Sam Eagle, and Kermit the Frog accompany various characters on their adventures. Hijinks ensue, including treasure map theft, treachery, duplicity, and daring rescues — all pirate media staples, of course!

Like any adaptation, Muppets Treasure Island takes plenty of liberties. But each one is for the delight of the audience. In the end (spoiler alert) the infamous treasure is even recovered. Alternatively, most dramas use the enigmatic hiding spot as a continuation of the legend for both the characters and viewers.

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One Piece

• Released: 1997 (manga), 1999 (anime), 2023 (live action)
• Features: inspiring optimism, hours of pages/footage

Manga and anime encompass countless dramas and spectacular stories. These Japanese storytelling mediums are perfect for telling a wide variety of tales, including those of piracy. In One Piece, the compassionate Monkey D. Luffy leads this extraordinary tale of a young man intent on finding Gold Rogers’ treasure and becoming king of all pirates. Captain of the Straw Hat Crew, Luffy showcases a lust for life (and meat!), plus an infectiously optimistic outlook. His crew mates, particularly Zoro, Nami, Sanji, and Usopp, round out every episode to create dynamics that make us both laugh and cry.

Additionally, proper anime adaptations into live action are rare. Yet Netflix’s One Piece is just as good as the animated series. Sometimes, fans consider it better for its ability to truncate a 1,000+ chapter/episode story into more digestible chunks. Netflix also approaches its diverse casting with far more sensitivity than its ’90s-era predecessor. Now, everyone’s looking forward to One Piece season 2, set to release on the streaming platform on March 10.

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Liveship Traders Trilogy

• Released: 1998 – 2000
• Features: innovative fantasy, complex characters

Immerse yourself in fantasy as it’s meant to be written with Robin Hobb’s Liveship Traders trilogy. These three books are part of The Realm of the Elderlings, a set of interconnected trilogies and series by the same author. While many of the characters are nigh-insufferable, their deeds and dynamics are remarkably compelling. Each book is more intense than the last, culminating in a brilliant end that will leave readers breathless, dizzy, and aching for the first pages of the next trio.

In Ship of Magic and the subsequent books, characters sail aboard liveships. Their figureheads are almost living souls, fashioned out of a magical substance called wizardwood, which gives them the ability to speak and guide themselves through the water. These liveships have thoughts and feelings, as well as bonds with their captains. However, the tides can quickly turn when rapscallions and ignoble villains, or perhaps sea serpents, are added to the mix.

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Treasure Planet

• Released: 2002
• Features: heartwarming relationships, amazing animation

Often, children’s animated movies deliver some of the most poignant life lessons. Treasure Planet, a science fiction version of Treasure Island, follows Jim Hawkins on a quest to change the direction of his life — before it’s changed for him. Down on his luck and always on the run from the law, Jim wants to explore the stars. But he doesn’t get the chance until he’s inadvertently caught up in the age-old feud between Billy Bones, Captain Flint, and Silver.

Jim finds a father figure in Silver and an adventure of a lifetime alongside a mutinous crew, an anthropomorphic blob, and a silly robot. Treasure Planet is also rounded out by a sweet love story as well as a heartfelt mother-son relationship.

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Firefly and Serenity

• Released: 2002 (series), 2005 (movie)
• Features: creative genre-blending, cool world-building and lovable characters

What’s better than pirates? Space pirates! And maybe a dash of cowboy-Western vibes, too. Firefly season 1 — the first and only season — combines all these elements for a planet-hopping party of infinite potential. In the pilot, Captain Malcolm “Mal” Reynolds picks up cargo and finds himself with two intriguing stowaways instead. What follows is a series of misadventures full of humor and heart alike. The episode “Out of Gas” is also a particularly impressive bottle episode that can be enjoyed on its own, out of context from the wider plot. But it sure hits harder when you care about the characters!

Although not very popular upon its initial release (the sci-fi show was canceled after a single season), Firefly has since developed a cult following. Thankfully, the cast and creators were able to finish some of the story with the follow-up movie Serenity. Comic book writers and artists have also expanded the world with various limited runs.

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Black Sails

• Released: 2014 – 2017
• Features: stellar acting, well-researched topics

Mark my words. Black Sails is, in many ways, comparable only to The Wire (2002 – 2008). And that’s because once you’ve watched Black Sails, there’s very little that can ever be as good. This drama series is heavily inspired by the Treasure Island novel, but grounds the children’s story into something far darker, more mature, and historically accurate. A prequel of sorts to Treasure Island, Black Sails explores the complex relationship between John Silver and James Flint, which led to the strange mix of resentment and respect in the characters’ initial introductions.

Yet Black Sails is also so much more. With a large and awe-inspiring ensemble, the STARZ original series delves into politics and identity, especially those considered unsavory by England. Women and enslaved people fight for the power they are owed in a world that continuously unmoors their every effort. Between the revenge, political intrigue, and never-ending betrayals, Black Sails is as entertaining as it is groundbreaking.

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Princeless: Raven the Pirate Princess

• Released: 2016
• Features: sapphic love stories, exciting art

Part of the Princeless series, Raven the Pirate Princess tells the story of an all-female crew on a vengeful high-seas crusade. With her title of “pirate queen'”stolen by her greedy brothers, Raven Xingtao seeks to reclaim her fleet and legacy by any means necessary. This spin-off comic book features a non-linear narrative, jumping between Raven’s past with her family as well as her present with her refreshingly diverse, highly capable crew members.

Comics, like many mediums, are a place where women are frequently undervalued or devalued. They are used exclusively as props and pinups. By putting women at the forefront of the story, Raven the Pirate Princess displays a dauntless female lead worthy of icon status. Plus, it helps us remember the importance of real pirate women like Anne Bonny and Mary Reed.

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Our Flag Means Death

• Released: 2022 – 2023
• Features: hilarious bits, queer main couple

Our list includes a healthy mix of comedies and dramas. Our Flag Means Death is pretty firmly rooted in the former, with a dash of tragedy just to keep things interesting. Essentially an office comedy, this delightful pirate show finds well-to-do English gentleman Stede Bonnet roughing it with a crew as unfamiliar with manners as he is with what it takes to be a fearsome pirate. The series utilizes actual historical pirates including Blackbeard to lend some credence to its stories, but make no mistake: This is (mostly) fictionalized.

Still, Our Flag Means Death touches on a lot of underrepresented aspects of real piracy and seafaring, including the same-sex union ceremony of matelotage. And whereas many television comedies like to tease queer couples without actually representing them, OFMD never queerbaits. Sadly, HBO controversially canceled the series after its second season to the shock and disappointment of many fans worldwide.

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What are your favorite pirate stories in pop culture? Did we miss the biggest treasure in your heart? Share your savviest story picks at side.show/geekgroup or in the Sideshow Social Network. And as always, don’t forget to Let Your Geek Sideshow!