Avast, ye scurvy blaggard! Gather round while I spin ye a yarn of brave men, big ships, and seeking treasure. The mythology of pirates has transfixed audiences for decades, and from the silent era to today, they've been a mainstay of visual storytelling both on the big and small screens.
With the popularity of HBO Max's Our Flag Means Death rising, now seems as good a time as any to revisit some classic pirate stories from the past and immerse yourself in this strange, violent but weirdly idyllic world, where men were free and lived and died by the sword as the hapless British Navy chased them around the Caribbean.
Crossbones (NBC, 2014)
An overlooked candidate for another list topic (shows unjustly canceled after one season), Crossbones took an exciting concept and ran with it: What if instead of dying, Blackbeard lived past his supposed demise in 1718, continuing to operate clandestinely in a secret location in the Caribbean?
Played by expert thespian John Malkovich, this version of Blackbeard is less mad pirate and a more cold, calculating Machiavellian power broker. He rules his own kingdom of outlaws and miscreants - who, of course, don't make for the most loyal of subjects. At the very least an interesting take on the legacy of the world's most famous pirate, Crossbones is worth tracking down.
Captain Blood (dir. Michael Curtiz, 1935)
The second adaptation of the 1922 novel of the same name, Captain Blood is a significant film for many reasons. It was one of the first "talkies" that was a big-budget action-adventure on the high seas, casting sword-fighting legend Errol Flynn in the title role, and also stars future Sherlock Holmes Basil Rathbone.
Flynn's performance made him a star, establishing him as the successor to Douglas Fairbanks and a "symbol of an unvanquished man" during the Great Depression. The critics of the period praised the production's ambitious action sequences while criticizing its fairly straightforward storyline - clearly a predecessor for modern blockbusters.
Laputa: Castle in the Sky (dir. Hayao Miyazaki, 1986)
Notable if for no other reason than being Hayao Miyazaki's first big hit at the American box office, Laputa: Castle in the Sky follows the adventures of a boy and girl who are trying to keep a magical crystal from the army, a group of secret agents, and a family of sky pirates while trying to locate a legendary floating castle.
If the phrase "sky pirates" didn't immediately pique your interest, then what hope is there for you? Blending Miyazaki's visionary animation style with a narrative that embraces the adventurism of pirate life as a gateway to independence and self-knowledge - told of discovery that are hallmarks of Miyazaki's coming of age narratives.
Captain Phillips (dir. Paul Greengrass, 2013)
Though most films in the pirate genre tend to depict what is commonly referred to as the Golden Age of Piracy, taking place around 1650-1730, the fact is the problem of piracy still very much exists today. This is much less of a romantic fantasy and much more a confronting reflection of economic inequality that forces these men to take these extreme actions.
Although dramatizations of this are few and far between, the most definitive is this 2013 collaboration between Paul Greengrass and Tom Hanks. Depicting the 2009 events surrounding the Maersk Alabama cargo ship and Phillips' subsequent bravery in negotiating with the captors for the crew's safety, Captain Phillips is a tense, compelling watch.
Black Sails (Starz, 2014-2017)
Functioning as a prequel to Treasure Island, Black Sails follows the exploits of a young John Silver as he navigates life alongside some iconic names from the annals of piracy. Blending real-world historical figures with fiction, coupled with a high production budget, Black Sails is one of the better offerings in the genre.
It does have a very "Starz" vibe, full of nudity and grime, but that too reflects and aids the nature of the storytelling. It removes the rose-colored filter many adaptations have towards these men and presents them much more realistically - as grimy, traitorous back-stabbers who would probably work well together if they could remotely trust one another.
Hook (dir. Steven Spielberg, 1991)
While Blackbeard is probably the most famous real-life pirate, the competition for his fictional counterpart is indeed a fierce one. Although an argument could be made for Long John Silver, most kids' first introduction to the pirate as we see them in our mind's eye is none other than Captain Hook, Peter Pan's sworn nemesis.
Maligned at the time, when looked at through a modern lens, Hook is a surprisingly good watch. Essentially, it does the Cobra Kai thing 30 years before Cobra Kai existed and re-contextualizes a well-known story by looking at the plight of the antagonist from the other side of the fence. Of course, this is helped when Dustin Hoffman plays the wronged party with panache and flair.
The Crimson Pirate (dir. Robert Siodmak, 1955)
By the time this film was made, the pirate genre was already 30 years old - apparently more than enough time for the genre's conventions to be lampooned. More than 60 years before Our Flag Means Death, The Crimson Pirate skewers the Douglas Fairbanks/Errol Flynn pirate films with its tongue firmly planted in its cheek.
The only film on this list to enjoy 100% on Rotten Tomatoes, it was doing something right. Playing like an early version of a Mel Brooks parody, The Crimson Pirate actually started as a serious pirate story until the director got his hands on the script and gave it serious modifications. The result is funnier if you've seen the films it's parodying but enjoyable regardless.
The Pirates: Band of Misfits (dir. Peter Lord, 2012)
A product of animation legend Nick Aardman's studios, the unique nature of the claymation presentation should be enough to get most avid film lovers to at least give this one a look. Set during the crackdown on piracy in the reign of Queen Victoria, this band of misfits rushes to establish a name for themselves even as the golden age of piracy is crumbling around their ears.
Between the animation style and the stellar voice cast, with the likes of Hugh Grant and David Tennant, this is a fun watch for all ages - which can't be said for a lot of modern pirate films. Not to mention the sense of fun and humor the film has in spades. This might be a good palette cleanser from this list's more violent, serious live-action fare.
Pirates of the Caribbean: Series (2003-2017)
Few character introductions are as iconic and well-thought-out as the first time we're introduced to Captain Jack Sparrow. Sailing in from who knows where on a tiny boat that is slowly sinking, we see him scrambling to keep afloat - only to stop and pay his respects to his fellow pirates as they hang as a warning. The boat stays afloat just long enough for Sparrow to stride confidently onto the jetty and into our collective imaginations.
Throughout five films of varying quality, what makes audiences keep coming back is Johnny Depp's performance. While maybe not as storied as Long John Silver or Captain Hook, Jack Sparrow is the most famous fictional pirate of the 21st century. Add to that plots that delve into all manner of maritime mythology, and you have a heady mix that makes for a great weekend binge.
Honorable Mention: Assassin's Creed IV: Black Flag (2013)
OK, so this isn't a television series or film. But in terms of immersion into a story of intrigue and adventure on the high seas, few have been as effective as Ubisoft's take on the genre in the fourth Assassin's Creed title, Black Flag. You play Edward Kenway, an opportunistic privateer who gets swept up in the assassins vs. templars conflict quite by accident.
This was a refreshing change of pace for the series, and Edward was a nice change of pace from the dour Connor of the previous title. But more than that, Ubisoft renders a period-accurate open-world version of the Caribbean and allows you to explore it at will as the captain of your very own ship. In terms of pirate storytelling, this is close to the pinnacle, as it allows you to write your own story as a pirate essentially - you can play the main story as you please, but you're in control of your crew and ship. It makes for a very immersive experience, and as cliched as this phrase is in game criticism, it really does make you feel like a pirate.