The Greatest Pirate Movies of All Time

Originally published 1/16/10 at geekinthecity.com

There was a time during the Golden Age of Hollywood in which pirates were king. Flynn, Fairbanks and the like controlled the silver screen as if she were their own captured prize, stolen from haughty English merchants who dared to sail too close to their flotilla. Swashbuckling, pillaging and wenching were commonplace an the movies and then suddenly, for some altogether unknown (and egregiously unnecessary) reason, the pirates went away. Long they slumbered in their dens, preparing for their glorious return to the forefront of American cinematic culture. And now, after what as seemed like an eternity, the pirates have returned. Sparrow, Barbossa and Davy Jones are avatars of this long-forgotten mainstay of Hollywood. So it is now that we celebrate these brigands, these ninja-stomping privateers, with a chronicle of the greatest pirate movies of all time. And believe me, what follows is a true listing of some of the finest sea-bound exploits that the world has ever laid their eyes on.

Raise yer tankards and make ready lads… here there be pirates!

Honorable Mention: Pirates (2005)

Yes, the porno. Despite your personal feelings on the genre (porn, not pirates), there is little doubt that Pirates was the most successful skin flick to cross over into the world of modern cinema. It became the highest grossing adult film of all time and even saw the release of an original soundtrack, which is something of an oxymoron for an industry that has never been touted for its er, musical prowess. Pirates may have never been released in theaters (well, not the ones you can take yer powder monkey to) but it garnered enough attention from the Depp-frenzied pirate fandom to make its way to video rental chains worldwide. In fact, Digital Playground, the film’s “studio,” found the demand for the movie so great that they re-cut the movie with an R rating. Which begs the question, what good is a porno without all the money shots? Surprisingly, pretty damn entertaining. Pirates is a genuinely fun flick that embraces the bravado of Pirates of the Caribbean along with a generous dose of good old-fashioned American sleaze. You can track down a copy of the R rated cut on Netflix and you’ll feel only slightly less dirty for doing so.

5. Peter Pan (2003)

The greatest film adaptation of J.M. Barrie’s renown novel suffered the cruel and untimely fate of being released in theaters a mere week after Lord of the Rings: Return of the King. Sadly, the movie had little hope of garnering the attention of the hobbit-crazed box office crowd. An unfortunate thing indeed, as director P.J. Hogan’s translation of the oft-told story was both literally accurate and visually stunning. From Jeremy Sumpter’s performance as the titular character to Jason Isaacs’ brilliant turn as the venomous Captain Hook, this is one swashbuckling fantasy that transcends both genres to become something truly timeless.

4. Muppet Treasure Island (1996)

As I was compiling this list over the past few weeks, I contacted many of my pirate brethren for their input. After all, who better to formulate and judge a listing of classic pirate films than a swaggering band of miscreants and rogues? Over many pints it was debated which movies were the boldest and most worthy of brethren approval. Through it all, this was the one film that kept getting mentioned. From seadog to wench, rogue to ne’er-do-well, each of my mates presented this challenge: “You’ve got to put Muppet Treasure Island on yer list!” I suppose the appeal is obvious. Muppets, Tim Curry, Billy Connolly, showtunes, pirates… there are few better things in life. Put them all in one move and you get, well… this. Can’t say that it isn’t a damn fine film, so the brethren must be right.

3. Pirates of the Caribbean: Curse of the Black Pearl (2003)

This film certainly has endured a lot over the past six years. From it’s kitschy concept (a movie based on the Disney ride?!) to unusual casting (Johnny Depp?!) to a surprising box office impact ($300 million?!), this flick remains as one of the most significant of the decade. Regardless of your feelings on the Pirates of the Caribbean franchise, there is little doubt that Disney’s initial offering was something special. With a wink of his eye and a stagger in his step, Depp ushered in an entire subculture of pirates enthusiasts. That’s something even Errol Flynn couldn’t do. But Jack Sparrow be damned, Curse of the Black Pearl showcased every piratical trick that Disney could muster. Geoffrey Rush did his best Robert Newton impersonation in a brilliant turn as the villainous Hector Barbossa. Then there were the ships…. the ships! From the Dauntless to the Interceptor and the Black Pearl herself, these were the true standout characters of the film. With two admittedly sub par sequels, the legacy of the Pirates of the Caribbean franchise may not be the shiny doubloon it once was. However, there isn’t a movie in the past fifty years that has had a greater impact on aspiring swashbucklers than this one.

2. Pirates of the Great Salt Lake (2006)

Chances are, you haven’t seen this film… and that is something we shall have to remedy. It was nothing short of an enormous tease to pirate fans when Pirates of the Great Salt Lake was initially announced. Touted as being a pirate film designed specifically for pirate fans, it had the national support of a niche audience while still hoping to capitalize on the popular allure of the cinematic swashbuckler . Pirates of the Great Salt Lake tells the story of Flint & Kirk, two Utah natives who decide that life had become far to mundane for their tastes, and that their fortune lay upon the great sea… in a life of piracy. This s a rare film that includes every critical element that one might expect from a pirate movie: buried treasure, murder, ghosts, gypsy curses, wenches, a commandeered ship, backstabbing, plundering and even a walk-on performance of an angelic Native American narrator. Director E.R. Nelson mixes all of these essential components with such fervor that you can’t help but to grab an eyepatch and give yourself over to the adventures of Flint & Kirk. By the time that you reach the story’s satisfying end, you’ll undoubtedly be ready to embark on a life of adventure on the high seas. This move isn’t just about pirates, it inspires pirates. A feelgood cutthroat flick for certain.

1. Captain Blood (1935)

Simply put, Captain Blood is pure piratical brilliance. It was the first partnership of Errol Flynn and director Michael Curtiz and is quite possibly the greatest. Flynn, a last-minute addition to the film (he replaced Robert Donat at the start of shooting) undoubtedly sculpted many of his Hollywood creations from the mold of Doctor Peter Blood. Dashing yet learned, adventurous yet methodical, there is a bit of Captain Blood in every pirate who has graced the silver screen since Flynn introduced him in 1935. A slave-turned-pirate whose strict moral code endeared him to his crew and made him enemies of both the Crown and a host of other buccaneers-for-hire. One of the most memorable scenes from Captain Blood features Flynn, in the heat of battle, using a dagger to slice to a mainsail, slowing his descent from the crow’s nest to the the carnage of a heated boarding party below. This image, like so many other in the movie, helped to invent the swashbuckling genre of pirate films in Hollywood. A noble feat indeed, and worthy of distinction as the greatest one of it’s kind.