As abominable as their historical counterparts frequently were, audiences around the world have always been fascinated with the idea of pirates. Roguish figures who live exciting lives outside of the law – dodging the authorities, plundering ships, and having their names whispered in fear and admiration by sailors near and far – pirates will likely always remain a point of interest for viewers everywhere. After all, who among us hasn’t briefly considered quitting their day job, living life as an outlaw on the high seas, napping under a Caribbean palm tree, sipping rum, free from any semblance of responsibility or earthly laws?
Of course, this picturesque view of piracy is far from the truth, most buccaneers being notorious figures who killed, terrorized, and stole their way to infamy. As it is, our view of piracy has largely been the product of movies and television, pirate films being a favorite genre of Film among audiences since the early days of silent pictures.
Over the years, pirate films have ebbed and flowed in popularity, sometimes coming back in vogue in unexpected new ways. From early movies starring Errol Flynn and Douglas Fairbanks to newer family-friendly films from Disney, here are some of the greatest movies to feature rampaging bands of corsairs in action, ranked from best to worst.
Captain Blood
Nearly 90 years since its release, Captain Blood still remains the definitive entry in the pirate genre. What High Noon did for the Western, Captain Blood did for the swashbuckler, setting many of the stereotypes and key components for the genre moving forward. A loving adaptation of Rafael Sabatini’s best-selling book (itself loosely based on the filibuster career of Henry Morgan), it jump-started the career of Errol Flynn, and gave the entire nation hope in a time of great uncertainty (the Great Depression).
Pirates of the Caribbean: The Curse of the Black Pearl
In 2003, Disney did the unthinkable. After the box office disaster of Cutthroat Island seemed to signal the end of the pirate genre, the company greenlit a film based on their popular theme park attraction, Pirates of the Caribbean. Fortunately, the decision proved incredibly successful from a monetary and critical standpoint, Disney ushering in a new interest in pirate movies and also establishing one of the most popular fantasy franchises of the 2000s.
Treasure Island
Adapting a novel is never easy, especially when the book is considered as universally beloved a classic as Robert Louis Stevenson’s seminal Treasure Island. Faithfully translating much of Stevenson’s text for the screen, Treasure Island also continued to develop the pirate genre as we know it today. For ample proof of this fact, just look at Robert Newton’s excellent portrayal of Long John Silver; with his missing leg, gold-obsessed parrot, and grizzled voice, he became the stereotypical image of a buccaneer for decades to come.
Captain Phillips
Offering a very different portrayal of piracy than most other films on this list, Captain Phillips is a harrowing biographical film centered around its historical counterpart (merchant sailor Richard Phillips) and his brush with Somalian pirates in 2009. Held hostage by his captors for four tense days, Captain Phillips shows that, in some parts of the world, piracy is still very much alive, and that it’s far from the romanticized image presented in most Hollywood movies.
Muppet Treasure Island
Many adaptations of Treasure Island have been released over the years, but few surpass 1996’s Muppet Treasure Island. Retaining most of Stevenson’s original storyline and blending it with the humor and characters of the Muppets troupe, it’s a comedy adventure film that continues to delight children and older audience members alike.
The Black Pirate
Before Errol Flynn, there was Douglas Fairbanks, the most famous actor of his generation and perhaps the first proto-typical action star within Hollywood. Having made a career as a dashing desperado with roles like Robin Hood and Zorro, Fairbanks brought his trademark charm to his role in 1926’s The Black Pirate, one of the best pirate movies of the silent era. Holding up surprisingly well in the near century since its release, it’s a movie that should be on every film aficionado’s must-watch bucket list.
The Sea Hawk
Given Errol Flynn received his first start starring in Captain Blood, it shouldn’t be surprising he went on to appear in a number of pirate movies in later years, the best of which is his 1940 film, The Sea Hawk. A roving adventure film made to reflect Britain’s ongoing struggle against Germany at the start of World War II, it’s among Flynn’s overall greatest films – political allegories aside.
The Princess Bride
It’s difficult to know exactly what to describe The Princess Bride as, the whole film feeling like a feature-length fairy tale. With its emphasis on sword fights, ship chases, and the Dread Pirate Roberts, though, a definite argument can be made that it belongs firmly in the swashbuckler genre. A fan-favorite film from generation to generation, it’s among the most perfect films ever made, with viewers across every age spectrum having an unfettered great time while watching it.
The Pirates! Band of Misfits
Aardman Animations is assuredly more well-known for Wallace & Gromit, Shaun the Sheep, and Chicken Run, but that doesn’t mean the studio’s lesser-known movies aren’t equally great in their own right. For example, just look at the hilarious high seas antics of The Pirates! Band of Misfits. A humorous spoof of the pirate genre, The Pirates! does a remarkable job satirizing most other films on this list, adding in a healthy dose of Aardman’s trademark eccentricity and light-hearted zaniness.
The Crimson Pirate
By the 1950s, the pirate film had been done to death, most later films offering little to anything new that helped reinvent the genre and hold audiences’ interest. Fortunately, that all changed with 1952’s The Crimson Pirate, a more absurdist spoof of the pirate movie that helped reinvigorate the genre. Utilizing a more flexible approach that didn’t strictly adhere to historical precedent, The Crimson Pirate’s lightweight atmosphere helped it become one of the better pirate movies of the 1950s, a decade that saw the genre begin to significantly wane in popularity.
The Goonies
Like The Princess Bride, describing The Goonies as a pirate movie seems like a stretch, but given the central premise of lost pirate treasure, it’s a natural description to apply to the movie. One of the main narrative influences on Stranger Things, it’s like a pirate version of E.T., a movie where, instead of UFOs, aliens, and secret government agencies, you have booby traps, derelict pirate ships, and a bumbling family of fugitives.
The Pirates of Penzance
It’s hard to think of a GIlbert & Sullivan opera more well-known than The Pirates of Penzance. Having been performed across the ages since the musical was first presented in 1879, The Pirates of Penzance eventually made its way onto film with 1983’s film of the same name. Gorgeous in terms of its cinematography and expertly employing Gilbert and Sullivan’s comical lyrics and characterization, it’s among the most underrated musicals of all time.
Peter Pan (2003)
Realistically, you can add any version of Peter Pan to this list, starting with Disney’s animated version from 1953 and ending with David Lowery’s most recent take on the story, Peter Pan & Wendy. However, in terms of its faithfulness to J.M. Barrie’s original play, 2003’s Peter Pan surpasses them all. Just light-hearted enough to appeal to kids while exploring some of the most fundamental aspects of Barrie’s story, it’s that rare fantasy film that every member of the family can heartily enjoy.
Treasure Planet
The third and final adaptation of Treasure Island on this list, Treasure Planet is just as ingenious a take on Stevenson’s book as Muppet Treasure Island, albeit in a far different way. Transposing Treasure Island into a sci-fi universe, it’s a brilliant contemporary take on the original nautical tale, translating it over to space opera with some clever changes (IE, a cyborg Long John Silver, a malfunctioning robot Ben Gunn, etc.).
The Black Swan
After 1935’s Captain Blood, 20th Century Fox tried to cash in on the success of the film by adapting another Rafael Sabatini novel for the big screen, finding the perfect story in the form of The Black Swan. Another seafaring adventure story, The Black Swan ironically feels like an unofficial sequel to Captain Blood, focusing on Henry Morgan (the inspiration for Peter Blood) and his crew as they put their piratical careers behind them, ruling over Jamaica as the island’s appointed governor.
