The Last Pirate Movies Ever Made: Revisiting PIRATES OF THE CARIBBEAN

A loving look back at Gore Verbinski's trilogy of oft-maligned, oddball epics.

Pirates of the Caribbean

What do you do when you’re asked to make a sequel to the last pirate movie anyone would ever make?

During production on the first Pirates of the Caribbean movie, there was a very real sense that the creative team behind it had conned a major studio into making a movie that should never have existed, a film that would be the last of its kind. Like westerns, the pirate movie had steadily fallen out of favor since its heyday in the mid-20th century, culminating in the apocalyptic failure of 1995’s Cutthroat Island. Now, a major movie studio was spending upwards of $150 million on a pirate movie – one based on a theme park ride, no less. Nobody expected this to succeed. As screenwriter Ted Elliott put it:

Basically we thought we may never get to write another pirate movie ever again. It was also possible no one would get to write another pirate movie ever again.

It’s true that Disney’s then-CEO Michael Eisner insisted on the clunky subtitle – one that director Gore Verbinski detested – in order to leave the door open for sequels, but that was only after he had cancelled production on the film following the disastrous performances of Disney’s prior theme park-based films, Mission to Mars and The Country Bears. Verbinski managed to reverse their cancellation after personally pleading with Eisner to let them continue, but even that felt like borrowed time. If this was to be the last pirate movie ever made, they were going to go for broke and make the biggest damn pirate movie the world would ever see.

But then, against all odds, The Curse of the Black Pearl was a hit. Not just a hit, but a bonafide cultural phenomenon. A massively entertaining swashbuckler that reintroduced pirates to our collective pop psyche and permanently cemented (for better or for worse) the superstardom of Johnny Depp. As you well know, a movie simply can’t have an impact like that without someone asking for a sequel, and ask Disney did. But once again, the question must be posed: when you’ve already made a film that was meant to effectively close the book on an entire cinematic genre, what the hell do you do for movies two and three?

When it comes to the Pirates movies, the answer, it seems, is to get weird.

Pirates of the Caribbean

Part 1 – Off the Edge of the Map

The first Pirates is a fairly straightforward adventure film. A perfectly manicured five act structure populated with an eclectic mix of eccentric oddballs and a layering of the supernatural in a manner similar to Spielberg’s own updated adventure flicks, the Indiana Jones movies. It probably would have been satisfactory if screenwriters Ted Elliott and Terry Rossio had taken an approach similar to Temple of Doom and Last Crusade and crafted another, wholly separate adventure for Jack Sparrow and the gang to embark on. But instead, Elliott and Rossio dove back into the original film and poked around in every corner and examined every throwaway line in order to reverse engineer a story with deep narrative and thematic ties to the original film while also expanding the world in which it takes place in ways that approach modern mythmaking. A story that sees our heroes wrestling with the burden of love, the relentless march of time, and the weight of immortality, all while squaring off against the Devil himself and something worse still. A series that begins with a character who is too hung up on propriety to confess his love to the woman who clearly loves him back and ends with this same character literally giving her his heart for safekeeping.

But I’m getting ahead of myself.

The Pirates sequels were not received well upon their release, and time only seems to have cemented the popular disdain for them. Even those who will concede the merits of the first film tend to hold up its sequels alongside the likes of Transformers as monoliths of bloated, incoherent, blockbuster trash. To be perfectly honest, I once fell in line with this axiomatic thinking. Having not revisited them since their initial release, their merits began to fade from memory while the negative popular consensus became cemented as truth. It wasn’t until I returned to this trilogy prior to the release of the fourth film in 2011 (which may as well not exist for the purposes of this essay) that I found myself falling head-over-heels for these weird, ambitious, wildly imperfect films.

And they are; imperfect, that is. It’s no secret that Verbinski and company were forced to start the two-movie shoot before the screenplays for both films had been finished and whole sequences had to be planned and storyboarded before the final drafts were in. That lack of completed scripts leads to a pair of somewhat lopsided movies. Dead Man’s Chest gets the lion’s share of the big setpiece moments while At World’s End, at times, strains under the weight of firming up the intricate mythology that was only hinted at in the previous film. These films don’t fit into the neat and tidy five act structure so expertly employed by Curse of the Black Pearl, instead they wind up being a bit more shaggy and meandering. But that ends up being part of their charm.

These movies don’t have that veneer of spit shine that generally serves to make big studio blockbusters as inoffensive to as many people as possible. Fact is, they just plain didn’t have time. The same constraints that forced these movies to begin shooting without a finished script also afforded them the freedom to be absolutely bonkers, and when you pair that with a filmmaker like Gore Verbinski, the results are a delight to behold. We now recognize Verbinski as a notoriously weird filmmaker, but following his debut feature, MouseHunt, there was a stretch there where he seemed to be endeavoring to make more “respectable” films. It was Pirates that really gave him the opportunity to let his freak flag fly, and he flies it even more proudly on its sequels.

Sequences like the Terry Gilliam-inspired fever dream of Davy Jones’ locker or the extended Loony Tunes cartoon featuring the cannibalistic Pelegostos tribe have limited function within their respective films, and probably would have been jettisoned long before cameras started rolling had this followed an “ideal” production path, but these zany diversions add to the almost punk rock sensibilities of the films. They don’t care if it’s strictly necessary from a functional storytelling perspective, they don’t care if it’s odd or awkward or in poor taste, it’s fun, goddamnit, so it’s in the movie.

The same goes for the structure of these films. There’s not the perpetual forward momentum that characterizes most blockbuster movies, instead Dead Man’s Chest winds up being closer to the stop-and-start structure of The Empire Strikes Back while At World’s End is built like a game of Mouse Trap with the bulk of the time given to constructing this elaborate, Rube Goldbergian machine that pays off in a breathlessly spectacular climax in the final hour of the movie. The structural perfection of Curse of the Black Pearl remains an absolute delight, but there’s something to be said for straying away from the well worn path of typical blockbuster filmmaking.

In fact, there’s not much that’s typical at all about the Pirates sequels. Sequels generally tend to fall into one of a few different categories. There are the sequels that essentially remix the scenario from the first film, remaining structurally similar but with altered specifics (see: Ghostbusters II, Back to the Future Part 2). There are also sequels that follow through on story threads that were intentionally left hanging in the previous film (see: Star Wars, virtually every adaptation of a serialized story). And then there are the ones that function as completely self-contained stories that happen to feature familiar faces (see: James Bond, Mad Max). The Pirates sequels did something different entirely. They took a film that was intended to be self-contained and retroactively recontextualized dead ends to appear as deliberate set-ups as well as expanding already completed character arcs in ways that feel like a genuine continuation rather than a fresh start. It’s an incredible feat of narrative sorcery, and its only real peer is the Matrix trilogy.

In terms of plot, Elliott and Rossio latched onto little things: the reference to Jack’s “brush” with the East India Trading Company, the fact that the specifics of how Jack’s “broken” compass works are never explained, and the never stated reality that Will essentially killed his father by breaking Cortez’s curse. Tiny footholds like these gave them the jumping off point to tackle the task of transforming a single film into an epic, three part saga, but the real magic comes in the way Dead Man’s Chest and At World’s End deepen and strengthen the themes at the heart of the first film.

Pirates of the Caribbean

Part 2 – What a Man Can Do, and What He Cannot

Our pair of leads – Will Turner and Elizabeth Swann – each have arcs that culminate in a fairly satisfying way in the original film. Will, who is introduced to us awkwardly attempting to fit in with high society and inadvertently breaking the first thing he touches; he is a man out of place. Despite being no more than a lowly blacksmith, he clearly pines over the Governor’s daughter and trains with a sword for hours a day on the off chance that he might meet a pirate. And yet, when Elizabeth clearly displays her affections, Will shuts her down. It’s not his place. He doesn’t want to rock the boat. Meanwhile, Elizabeth is introduced dreaming about pirates and adventure on the high seas only to be forced into a corset and an arraigned marriage upon waking. Elizabeth bristles against her ill-fitting corset, but Will wears his by choice.

That’s likely the way they would have carried on, if not for the disruptive presence of Jack Sparrow, sailing in, with glorious fanfare, atop a dinghy that’s slowly sinking in the harbor. Jack’s grandiose posturing belies a more mundane truth. He’s a pirate, but one with an honest streak that crops up at the most inopportune moments. He can’t let Elizabeth drown and thus is found by Norrington and his men, he can’t murder Will in order to escape and thus is imprisoned, and as a result of these actions, he inadvertently sets their respective arcs in motion. Elizabeth’s first real encounter with piracy is literally a freeing experience as Jack removes her corset to save her from drowning. On the same token, Will asserts himself for the first time when Jack wanders into his blacksmith shop while fleeing from the guards.

The crucial thing that makes Jack work is that he’s not the protagonist of these films, but rather the human embodiment of an inciting incident. He’s a force of nature that disrupts the lives of everyone he comes in contact with, and the story is seeing how these characters respond to that disruption. Jack forces Will to confront his legacy and discover his place in the world while also inadvertently thrusting Elizabeth into a world of adventure where she is able to discover her capacity to shape her own fate unbound from the restrictions put upon her. It’s the classic hero’s journey: the heroes go on an adventure, learn about themselves along the way, and return home as stronger, more actualized people. But that’s not exactly how real people work. It’s easy enough to proclaim your love in front of a picturesque sunset, but how do you adjust to living life as this new person you’ve become? What of all your insecurities and inadequacies? If you didn’t think you were good enough before, what make you good enough now? If the life of a scoundrel fits you so naturally, what separates you from the most despicable among them? What do you really want most in life?

Pirates of the Caribbean

Part 3 – I Know What I Want

In spite of the title, the key object in the second film is not the Dead Man’s Chest, but rather Jack’s compass – a compass that points to whatever it is that its holder most desires. The ingenious problem of Dead Man’s Chest is that, despite having a magic compass, all of these characters are conflicted about what they want.

Robbed of their fairy tale wedding because of their ties to Jack Sparrow (again, a disruptive force), Will and Elizabeth are forced to wrestle with their demons and insecurities. While trying to secure an official pardon for Elizabeth, Will winds up being reunited with his father, a man he thought he had killed as a byproduct of breaking the curse of Cortez. Not only is Will absolved of this guilt, but he has the opportunity this time to save his father – a choice he was previously denied. Suddenly the most important thing in Will’s life is no longer Elizabeth, but rectifying a perceived mistake that he never actually made. If he can’t unburden himself of this baggage, how can he, in good conscious, get married?

Meanwhile, Elizabeth, true to form, manages to find her own way of escaping prison in Will’s absence. As she sails with Jack to rescue Will, she is confronted with the fact that there’s more of her reflected in this scallywag than she’d care to admit. Both of them have proven to be relentless opportunists, slyly able to manipulate chaos to their own advantage. Elizabeth, let’s not forget, managed to talk her way out of being murdered by Barbossa’s crew, found a way to escape the same island Jack was previously marooned on, insincerely accepted Norrington’s marriage proposal in order to save Will (indirectly killing a dozen or so members of the Royal Navy in the process), robbed the head of the East India Trading Company at gunpoint, and tricked a bunch of superstitious sailors into docking at Tortuga. While Will turned to piracy as a means of saving the people he cared for, Elizabeth embraced the life of a scoundrel for the sake of pure self preservation. If she’s so much like Jack, would being married to someone like Will actually work out?

As much as anything else, the Pirates sequels are a story about marriage anxiety, and Will and Elizabeth’s relationship struggles are mirrored in the villainous Davy Jones. Davy Jones was a man who loved the goddess Calypso so much that he agreed to captain the Flying Dutchman and ferry the souls of those lost at sea to the other side. The cost of this task was that he would only be able to see his love once every ten years, but after ten years, he returned to find that Calypso had abandoned him. Wracked with anger and grief, he carved out his heart and locked it away in a chest. His vulnerabilities hidden away from the world so that he could not be hurt again, but in the process transforming him into a cruel, heartless monster. The Devil of the seas, no longer helping lost souls find peace, but recruiting them to serve aboard his ship wherein they’re forced to share his cursed fate.

This is the predicament Will’s father has found himself in, having traded one curse for another. In order to save him, Will must kill Davy Jones, but there’s a catch: the Dutchman must have a captain, and if you kill Jones, you must take his place. Sailing for an eternity, only able to make port once every ten years. That’s the choice Will is faced with; spend eternity atoning for his sins in order to assuage his guilt, or attempt to bury his baggage to be with the woman he loves.

But Will is not the only one vexed by Jones. Jack finds himself on the run from Davy Jones who is coming to collect on an arrangement Jack made thirteen years prior: his soul in exchange for raising the Black Pearl from the depths. Dead Man’s Chest reintroduces us to Jack inside of a coffin, announcing to the corpse accompanying him that they’ll be making a side trip. And indeed Jack spends the rest of the film attempting to run from death, but no matter where he goes, death finds him. The Kraken pursues him on the seas, the Pelegostos mean to roast him alive, even the pirate haven of Tortuga isn’t safe as the disgraced former commodore, James Norrington, shows up seeking a bit of revenge. When death finally catches up with Jack, he attempts once more to run – abandoning his ship and his crew to be consumed by the Kraken as he escapes aboard the Pearl’s only longboat. But once again, Jack’s honest streak crops up and of the things he can do, allowing his friends to die to save his own life is not among them. Jack returns, allowing the crew to abandon ship, but Elizabeth knows that there’s only one way that this can end. Fully embracing her piratical nature, Elizabeth seduces Jack with a kiss, then chains him to the mast of the Pearl. She condemns him to die so that the rest can escape. In the end, Elizabeth finds that she is more ruthless a pirate even than Jack, and the weight of what that means for her – what it means for Will – is more than she can bear.

The end of Dead Man’s Chest sees our heroes laid low. Will could not best his demons, Elizabeth could not best her nature, and Jack could not best the Devil, but there’s something on the seas worse than pirates or curses or Davy Jones himself.

Pirates of the Caribbean

Part 4 – Just Good Business

As Will and Jack fight to claim the heart of Davy Jones, each for their own ends, Norrington manages to abscond with it and deliver it to Lord Cutler Beckett in exchange for a return to his rank in the Royal Navy. The Big Bad of Dead Man’s Chest is now under the unwitting employ of the East India Trading Company.

In the twilight years of the Western’s dominance of pop culture, the notion of these frontiersmen as living relics of a dead era became a fairly common theme. Films like The Wild Bunch, The Searchers, or any number of the Spaghetti Westerns from that era recontextualized these towering icons of American mythmaking as morally complicated figures living in a world that’s left them behind. While some of these themes begin cropping up in Dead Man’s Chest, it’s in At World’s End where they’re thrust to the fore.

Magic and mystery is disappearing from the world as the relentless march of progress, fueled by the demands of business, are filling in the blank edges of the map. As we come to know better the shape of the world, there’s no place for the untamed weirdness of the old world. At one point, the crew of the Black Pearl come across the Kraken, washed up on a beach, and as Jack gazes upon the rotting corpse of the creature he spent the whole previous film trying to escape, it is mournful. “The world’s not smaller,” he says to Barbossa, “there’s just less in it.”

Structurally, At World’s End is odd. A nearly three-hour film in which the first hour is spent effectively undoing the ending of the last film, but thematically this choice makes a certain amount of sense. These films were meant to serve as the last hurrah of a bygone era of cinema, and the story itself is about the last stand for a way of life that was becoming extinct. You may not get to live forever, but you’re alive in this moment, best make the most of it.

That’s the conflict facing Jack in this picture. As much as Jack functions as an unchanging agent of chaos – instigating conflict by his very existence and somehow managing to navigate through it unchanged – of the trilogy, At World’s End is the most focussed on exploring Jack as a character. The conflict between the person Jack is and the person he wants to portray himself to be remains consistent all the way back to his introduction in the very first movie. The legendary pirate, riding high atop the mast to the sounds of a swelling orchestra, contrasted with a man bailing water out of a sinking boat. Jack even states his philosophy in that same film: what a man can do versus what he cannot. Like the genre of the pirate movie itself, Jack was brought back from the dead and wants to find a way to live forever, to outlast a changing world that threatens to leave him behind, but can he do it? Can he abandon every other person in his life in order to be immortal or will his honest streak, as ever undercut his grandiose self-image?

He doesn’t, of course, because Jack doesn’t change, and that’s the point. However, that desire for control of one’s life, one’s legacy, one’s place in the world runs throughout the film. Davy Jones wanted control over his emotions, so he locked his heart away from the world; Beckett wants to control the seas, so he’s vowed to put an end to piracy; and Jack wants to kill Davy Jones to control his own mortality. Even the pirate lords of old felt this urge as they bound the goddess Calypso to human form in order to tame the seas for themselves.

Caught in the middle of it all are Will and Elizabeth, each seeking to find some sense of control as their relationship threatens to fall apart. Elizabeth, agonizing over her decision to leave Jack to die, feels she must bear the burden of this choice all on her own, while Will remains torn between saving his father and being with the woman he loves. But it’s only upon releasing this myopic need to impose your control on the world around you that anything can be accomplished.

As each of the nine pirate lords vote on which among them should be king, it is Jack’s vote for Elizabeth – the only pirate lord who didn’t vote for himself – that breaks the stalemate and forces the pirates out of their sanctuary in Shipwreck Cove in order to fight back against the East India Company. As they are facing down the overwhelming might of their enemies, it is Barbossa’s decision to release Calypso and the ensuing storm that buffers them from Beckett’s fleet. And as Jack has the opportunity to stab Davy Jones heart and claim immortality for himself, he abandons those desires in order to save Will from dying. Meanwhile Jones’ act of locking away his heart ended up being the very thing that made him vulnerable, and Beckett refuses to abandon his station as the Endeavour – his endeavors – falls to pieces all around him.

As for Will and Elizabeth, Elizabeth accepts Will’s marriage proposal, allowing herself to share her burdens with someone else as the two say their vows amid the chaos of a climactic battle, fighting in unison, defending each other’s backs as they’re joined in holy matrimony. And Will, once unable to commit to Elizabeth – too proper to confess his love, too hung up on his own baggage to be by her side – literally gives her his heart in a chest. Not hidden away from the world, but kept safe by the woman he loves. Yes, Will may be bound to serve on the Dutchman, but again, trying to control the future is fruitless. There’s only this one day, and Will plans to make the most of it.

Pirates of the Caribbean

Part 5 – End of an Era

Nobody should make a pirate movie again after we’re done. The end of an era.
–Gore Verbinski

Even as At World’s End concludes with Jack Sparrow sailing into the sunset to find the fountain of youth, there’s a feeling of finality. These closing moments are not meant to set up a sequel, but to assure us that, as ever, Jack is the same. Things don’t last forever; people die, the world changes, but life goes on same as it ever did.

The era of the pirate movie is over, and despite the enormous success of these movies, that doesn’t appear to be changing anytime soon. For all the impact these movies have had – Johnny Depp’s stardom, launching Keira Knightley’s career, establishing the precedent that you can make a movie out of literally anything – reinvigorating the pirate movie genre was not one of them. Beyond Disney’s own misguided sequels, there has not been much of an attempt to keep this genre alive, and that’s okay. These movies were not meant to spark a renaissance of seafaring adventures, but to build a monument to a bygone age of filmmaking. These movies were such a colossal undertaking – shooting in places that were never meant to support the infrastructure of a massive film crew, battling hurricanes, building ships, filming on the actual ocean, and creating gargantuan physical effects to pull off the films’ enormous setpiece moments – that the thought of trying to replicate it is downright insane. The fact that this production nearly collapsed under its own weight before it even started is a testament to the absurdity of this endeavor.

But it worked. They may not be perfect, but the level of spectacle that they managed to accomplish remains unmatched even ten full years after their release. Other impressive crowdpleasers have certainly come since, but none of this scale and this level of tangibility. These films that were meant to be the last pirate movies ever made, also, inadvertently, became the last of the American epics, the size and scope of which might never be matched, at least not in this same way. The fact that they also manage to tell a rich, compelling, and, best of all, complete story without falling apart at the seams makes them all the more spectacular in what they achieved.

And even as I write this, I know that many will scoff at this claim, but I’d hope that the fact that I’ve been able to mine more than 4,600 words of critical analysis out of these weird, silly movies would indicate that there’s more layers of meaning to these films than most give them credit for (and that’s even considering that I’m trying my damndest to not let this turn into a book). They’re dense, and awkward, and lopsided, but those tend to be the types of movies that stick in my memory. As much as I adore The Curse of the Black Pearl and admire its structural perfection, it’s not my favorite of these films. That honor goes to Dead Man’s Chest, an incredibly unusual film with some of the most evocative imagery I’ve ever seen in a major studio blockbuster.

Movies like these may never exist again, and, from a purely pragmatic perspective, perhaps shouldn’t have existed to begin with. Not once, but twice, Producer Jerry Bruckheimer along with Verbinski, Elliott, Rossio, and the rest of the immense teams that worked on these films took advantage of a unique moment in the history of the Walt Disney Company, when the CEO who would shortly be removed from his position was desperately throwing ideas at the wall to see what stuck. This team sailed beyond the edge of the map to bring a long-abandoned type of moviemaking back from the dead, and in doing so put every resource they had at their disposal into pulling off a monumental feat, the likes of which may never be seen again. That alone makes them worthy of recognition in the annals of cinema history, and who knows, maybe revisiting them after all this time might lead you to find something you never knew was there to begin with.

Sure as hell worked for me.

  • Amazing article. Warts and all, these three films are special. Moving, funny, spectacular and the kind of films one can imagine a child watching on a theater and, coming out of the screening, telling their parents they want to make movies.

    • Agreed 100%. Give it another 10 years and some breakout, 28-year-old director will cite these as major influences.