Last Updated on February 25, 2022
Johnny Depp reprises his iconic role of Captain Jack Sparrow in the latest PIRATES OF THE CARIBBEAN film, DEAD MEN TELL NO TALES, which is the only pirate-themed franchise currently making waves these days. But, swashbucklers have long been staples of Hollywood and have a history of adventure and action. Here is our ranking of the ten best pirate movies of all time.
PIRATES OF THE CARIBBEAN
It sounded like an awful idea. I mean, why would you make a film based on a theme park ride? Idiotic and yet Gore Verbinski and Johnny Depp crafted a rip-roaring adventure spectacle that revived an entire genre. While none of the sequels have lived up to the original, THE CURSE OF THE BLACK PEARL still ranks as one of the finest pirate movies ever made.
THE GOONIES
The most unique pirate movie on this ranking, THE GOONIES is the perfect blend of TREASURE ISLAND and INDIANA JONES. Few films of the 1980s are as beloved as Robert Zemeckis’ family friendly action film and none are more quoted by my generation. This is a movie that deserves to have been a long running franchise, but I will settle for One-Eyed Willie and the rich stuff we did get. Hey you guys!
HOOK
While I may not be the biggest fan of Steven Spielberg’s Peter Pan retelling, I respect that there is a huge fan base out there. From PJ Hogan’s take on the tale to the recent Joe Wright reimagining, the Peter Pan mythos is linked directly to the titular Captain whose dandy appearance and trademark appendage are as instantly recognizable as any character in movie or literary history.
CAPTAIN BLOOD
Legendary CASABLANCA director Michael Curtiz helmed this hit that put Errol Flynn and Olivia De Havilland on the map as Hollywood superstars. Very much the template for many pirate films that followed, the misleading title of this movie makes it seem dark and dangerous whereas this is an example of the perfect movie studio formula film executed without any issues.
NATE AND HAYES
A box office bomb when it was released, NATE AND HAYES was designed to capitalize on RAIDERS OF THE LOST ARK. Even though it failed to gain traction in 1983, NATE AND HAYES has since developed a devoted fan base. Definitely check this out for Tommy Lee Jones as the Indiana Jones-esque Bully Hayes and keep your eyes peeled for an action scene on a bridge that pre-dates a similar sequence in TEMPLE OF DOOM.
THE PRINCESS BRIDE
One of the most memorable romantic films of the 1980s, THE PRINCESS BRIDE also is very much a pirate movie. Cary Elwes imbues Westley, aka the Dread Pirate Roberts, with equal parts Errol Flynn and Douglas Fairbanks. A throwback to the epics of the 1950s, this is a contemporary masterpiece.
YELLOWBEARD
The idea for this film developed over a dinner shared by Keith Moon, Sam Peckinpah, Graham Chapman and Peter Cook. Chapman would eventually pen the screenplay and bring back several of his Monty Python mates along with other stars like Cheech & Chong and Peter Boyle. This comedy is part TIME BANDITS and totally crazy.
AGAINST ALL FLAGS
This 1952 swashbuckler stars Errol Flynn and Anthony Quinn as dueling pirates. But, it also is unique in that it features a prominent female pirate. Spitfire Stevens, played by Maureen O’Hara, is more than a mere love interest and represents one of the earliest representations of a female pirate. This is a fun, if underseen, adventure.
THE BUCCANEER
Many of you may not be familiar with this 1958 classic (or the 1938 original version). Directed by famed actor Anthony Quinn, THE BUCCANEER stars Yul Brynner in the title role with a supporting turn by Charlton Heston as Andrew Jackson. A fictionalized telling of Jean Lafitte and his involvement in the War of 1812, this is a great story from a period not often seen on the big screen.
TREASURE ISLAND
There have been countless versions of the classic Robert Louis Stevenson adventure story (including a great MUPPET version), but Disney’s 1950 film was and is the best. The first entirely live action Disney film and the first version of TREASURE ISLAND in color, this is a movie that holds up to this day and is a worthy entry on this list.
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