!!Specific films:
[[index]]
* ''Headscratchers/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl''
* ''Headscratchers/PiratesOfTheCaribbeanDeadMansChest''
* ''Headscratchers/PiratesOfTheCaribbeanAtWorldsEnd''
* ''Headscratchers/PiratesOfTheCaribbeanOnStrangerTides''
* ''Headscratchers/PiratesOfTheCaribbeanDeadMenTellNoTales''
[[/index]]

!!General:
* Has it ever been explained exactly how or why the ''Black Pearl'' is as fast as it is? It's established as being perhaps the fastest ship in the world within the series' setting, but according to the backstory, it was just a cargo/trading ship for the East India Trading Company that Jack was rather attached to. Did Jones raising it from the depths make it faster? Was it always that fast? If so, are all EITC ships that fast?
** The ''Pearl'''s being a one-time cargo ship doesn't rule out it ''also'' being exceptionally fast. Possibly it was originally built for high speed so that it could be used to transport time-sensitive goods, like priority mail and expensive fruits and meats.
** The Pearl is shown to be faster in "Curse of the Black Pearl" due to its rowers and being to go at incredibly fast speeds with the wind, presumably due to it being incredibly light. This is what enables it to catch up with the Interceptor, the fastest ship in the Royal Navy. The Pearl is faster than the Dutchman because the Dutchman is faster against the wind which is how it takes it's prey. With the wind, the Pearl robs the Dutchman of it's advantage.

* Barbossa needs to get over himself. Jack is so damn clever. Why won't he just build a fleet with him?! Barbossa hates Jack so much because Jack is sort of like a pirate White Prince compared to him: (1) His father's already a powerful pirate, (2) Jack's spoiled and probably didn't start out by the "sweat of his brow" and all that and (3) Jack got a top-rate ship for nothing while Barbossa lost everything he had in Europe and had to start again in the Caribbean. Barbossa needs a hug.
** Jack's father helped him, he didn't work for anything, and he got a ship for nothing? He sold his soul to an immortal demigod for his ship, found the compass himself, and then tricked his way out of the deal! That's not hard work? Granted, Barbossa still ought to give it up, simply because he'll never beat Jack's natural luck it seems.
** Then again, Jack isn't exactly the most... dependable guy. Would ''you'' keep him as your second-in-command? Or, CrystalDragonJesus forbid, as your commander? And of course, should they even agree on a you-command-these-guys, I-get-those-guys deal, there's the whole "Who gets to sail the Pearl?" thing.
** Jack and his father don't seem to get along much. In fact, Papa Sparrow seems to generally hate everybody. The idea that Jack is the pirate equivalent of a spoiled rich kid doesn't add up. If that were so, he'd be able to get another ship when Barbossa mutinied, or get his father to evict Barbossa.
*** 1) Yes, Barbossa clearly needs to get over himself, but in COTBP, Barbossa was willing to work with Jack at the end of the movie, and look what happened? He got shot in his chest! 2) Teague doesn't necessarily hate everyone, he's probably just a hard-ass Rules Nazi, (it ''is'' his job) and he seems to get along better with Jack than anyone else.
*** Taking into account the flashback from Dead Men Tell No Tales and the fact we know who his father is, Jack's name is probably Jack Teague, Sparrow is a nickname he gained because of how he beat Salazar. So its possible he either took the name Sparrow to get past his fathers name, or he is just unmentioned as Captain Jack "Sparrow" Teague.
** We also saw what happens at the start of the second movie when Jack gets his own ship: he's aimless, obtuse, won't explain himself to his crew and doesn't seem very concerned about their well being or opinions. He's a brilliant adventurer and pirate, but he's not a very good leader. Barbossa might have had some good reasons for leading a mutiny against him, since he does seem to be much better at actually commanding his crew. At least the second time around, Barbossa respected Jack enough to simply strand him at port, rather than on a deserted island.
*** You're overlooking the fact that Jack's only 'aimless' because his compass isn't working, so they don't '''have''' anywhere to go. Considering what happened with Barbossa, isn't it plausible that Jack didn't ''want'' to admit that he couldn't find the destination, in case the crew decided to replace him with someone who did?
*** The compass wouldn't work ''because'' Jack was aimless, not the other way around. It pointed towards his heart's desire, but he couldn't make up his mind on where he wanted to go. It's no insult to Jack to say that the very qualities that make him a brilliant adventurer also make him a bad leader. Davy Jones says as much when he responds to the news of the Black Pearl's mutiny with "then you were a poor captain, but a captain nonetheless".
*** The films give us no reason whatsoever to assume Jack as being rich, entitled, or otherwise advantaged just because his dad happens to be the Keeper of the Codex Pirata. For one, when do we ever see Captain Teague with so much as a ship to his name? For all we know, he could be "skint broke" like the original Brethren Council Pirate Lords, and behind the fancy title he might be merely a penniless bureaucrat. Financial power (or lack thereof) aside, Jack's dad doesn't appear to have much in the way of influence either. The pirates seem to only respect the Code when Teague is in the same room and will kill them on the spot if they don't - outside of the council chambers, the rules are regarded as suggestions and traditions at best, and "Code? What code?" at worst. Also none of the other pirates seem hesitant to move against Jack for fear of pissing off his "powerful" dad.
*** Expanded material mentions somewhere that Teague was a Pirate Lord back in his day, but he's since retired (though he did give his seat to Jack). Apparently Sao Feng also inherited his post from his father.
** In expanded material, it's explained that the ''Pearl'' was originally the ''Wicked Wench'', an East India ''Trading'' Company ship, captained by Jack who had left his pirate life behind him. She was sank by Beckett as punishment for Jack not transporting slaves and Jack was branded a pirate. Jack sold his soul to Jones for thirteen years as captain and returned to a life of Piracy.
*** Also when Jones raised it was renamed the Black Pearl by Jack because Beckett burned it, and when it was raised it kept the charred look, hence a "Black Ship".
** In the canon novel "[[Literature/PiratesOfTheCaribbeanThePriceOfFreedom The Price of Freedom]]", Jack meets a younger Barbossa on Shipwreck Cove and Barbossa owes Jack a debt for helping bring the rogue pirates who sunk Barbossa's ship to justice seeding the start of their friendship. Barbossa doesn't seem to show any resentment to Jack for being the son of a Pirate Lord and Barbossa even becomes a Pirate Lord because of Jack; the Pirate responsible for sinking Barbossa's ship was a Pirate Lord and knowing he's going to die. This Lord gave Barbossa his piece of eight when Barbossa visited him, actually making Barbossa superior to Jack for many years (depending when Teague retired and gave Jack his Piece of Eight making Jack a lord).
* What is with Beckett and his "just good business" CatchPhrase? Breaking your agreement with other people is ''not'' good business - it is, in fact, the opposite. Word tends to get around quite quickly if you stop keeping your end of the bargain when you negotiate with people, and in a situation like what Beckett was trying for with the East India Trading Company (a complete corporate monopoly of all trading routes), you ''need'' people to trust you - which they won't, if you've proven that you'd be inherently incapable of negotiating in good faith if your life depended on it. Otherwise, they start looking for methods that don't involve dealing with you to get what they want - and, when they're dealing with a ManipulativeBastard like Beckett, those ways will involve removing said bastard from power if at all possible, ''by'' any means possible.
** Then again, is it ''really'' good for business to keep someone like Jack Sparrow around? Beckett wasn't saying, "Breaking deals is good business," he was saying, "Getting rid of all the pirates is good business."
** Besides, it's hardly good business to leave a professional wild card like Jack Sparrow running around when you already know that he hates you (and you return the feeling). None of Beckett's merchant prince buddies would fault him for going back on that deal.
** That's not what "just good business" means. It's an echo, and its meaning changes, depending on who's using it and in what context. It's used as a justification for cruelty, dishonor, greed, and cowardice, and later Beckett repeats it when his ultimate defeat becomes reality - he never planned on losing, you see. But when he says it "to" Jack earlier, when he assumes he's won and Jack's come crawling for his forty pieces of silver, the lips say "good business", but the eyes say "[[EvilGloating owned]]!"

* What in the hell would have happened if Davy Jones stabbed his own heart?
** The simplest solution is just to have him suffer the fate of everybody else who stabs the heart - he becomes the captain of the 'Flying Dutchman'. Of course, as he's ''already'' the captain, this would produce no real change in his situation. Which would explain why he never bothered trying.
** Another idea is that there would either be some sort of [[RealityBreakingParadox tear in the space-time continuum]], or, even simpler, that [[AWizardDidIt magic]] would not physically allow him to stab his own heart.

* If both Jack Sparrow and Barbossa are pirate lords, why is Barbossa Sparrow's second in command? Shouldn't he have his own pirates, and not have to bother Sparrow?
** It's safe to assume that Barbossa only became a pirate lord ''after'' the mutiny mentioned in the first movie. He had something like ten years to do it.
** He was also an unkillable undead dude, as was his crew. He wouldn't find it difficult to kill another Pirate Lord and nab one of the pieces of eight. And Jack is Jack, if he didn't have one before he was marooned he would have picked one up somewhere.
** Barbossa was Pirate Lord of the Caspian Sea, where there's no other water sources leading into it and therefore not too many ships passing through, if any at all. So he probably just said "Screw this" one day and decided that he was better off as a first mate in one of the busiest seas in the world than a captain of an unpopulated water hole, assuming there were any other pirates, of course.
*** Actually, you might have to be a captain to be a pirate lord, but that's according to the highly suspect DVD extras.
** It was the Piece of Eight that made one a Pirate Lord. He had to be given the Piece of Eight by a former Pirate Lord, so when he did get it, he became that Pirate Lord. The Piece of Eight is proof of lordship, as Barbossa says when the Brethren Court meets: "Prove your lordship and right to be heard."
** Speaking of pieces of eight... at the end of the first film, Captain Barbossa is dead, and Ragetti isn't. And Ragetti has the wooden eye that was Barbossa's "piece of eight". Wouldn't that have made Ragetti the new Pirate Lord of the Caspian Sea?
*** Tia Dalma needed the Piece of Eight, but didn't know what it was. She brought Barby back to get him to tell her and help her, and Ragetti went along with it.
*** Knowing Barbossa, he probably never told Ragetti ''why'' the wooden eye was important, only that he had to keep it safe. So Ragetti never actually knew it was possible for him to claim Barbossa's title between films.

* Bootstrap Bill, Will Turner's dad, is still alive, and working for Davy Jones. However, he was one of the original Pirates that stole the Cursed Treasure in the first Movie. So when the Pirates, who kept turning into undead skeletons at night, left Bill for dead he chose to work with Jones. Did the curse still affect him as he became a Squid-man? Or is working for Davy Jones a way to end the curse?
** Presumably Will's blood sacrifice would have broken the turn-to-a-skeleton curse on Bootstrap if it was still in effect on him at the time of the first movie. Unfortunately for Bootstrap, this wouldn't end his debt to Jones, even if he ''had'' joined the ''Dutchman'''s crew in exchange for release from the medallion-curse's effects: remember, Jack's loss of the ''Pearl'' to mutiny in no way negated ''his'' debt to Jones, even though he never got his full 13 years of command.

* At the end of DMC, the SequelHook has the crew of the cast decide to rescue Jack simply for the purpose of rescuing Jack, believing that he pulled a HeroicSacrifice. Come the third movie, it seems like they are only doing it out of necessity (note the show of hands when Jack asks if anyone came along just because they wanted to see him again). That said, certainly the oncoming war would rearrange their plans, but it would have been nice if someone had SAID that.
** Elizabeth was motivated by guilt, Will wanted the ''Pearl'' to save his father, and Barbossa had his own agenda (which was also at least in part Tia's agenda), which is fairly clear at the end of DMC ''and'' pointed out by Jack in AWE. Pintel, Ragetti, Marty and Cotton all raised their hands for the "saving Jack just because they missed him" crowd, and while Gibbs didn't raise his hand, the way he rolled his eyes at Jack seemed to indicate both exasperation and affection. In short, there isn't a discrepancy between their motivations between movies- though of course the EITC is a much bigger threat in everyone's mind come AWE.
** The end of the second film implies that the whole point of their quest is to retrieve Jack, and regardless of their true motivation, Will and Elizabeth appear to be going along with it for the 'he was a good man' story. Come the next film, they are are required to retrieve Jack for the war, with that little pep talk at the end of DMC seemingly forgotten. Small in the grand scheme of things, but a bit jarring...
** Possibly their eagerness to go rescue Jack just for friendship's sake took a severe dip when Tia Dalma explained just how hard, long and risky the trip to the Locker was going to be?
** Or they ''initially'' wanted to rescue him for his own sake, but over the months of set-up work required to get the map to the Locker, guilt had time to work on Elizabeth's conscience and Will's concern for his father had time to fester.

* If Davy Jones wanted his heart-chest safe from mortals, why not just bury it deep underwater where nobody could possibly get it (with the technology of the time, that is)? Or at least under something more secure than two feet of sand and a box full of old papers.
** Ah, but was Jones really hiding the chest from his enemies, or was he putting the heart in a place where ''he'' wouldn't have to deal with it? Remember, this is the man (er, squid) who called his heart "that infernal thing", and his motive for tearing it out in the first place wasn't to make himself immortal, but to make himself unable to feel.
** One should also consider they're living in a universe where AllMythsAreTrue (at least the nautical ones); putting it underwater risks some ancient evil underwater creature eating it or something. Hell, if the Mermaids from the fourth movie decided to get curious they could kill him. So putting it in a far-away, abandoned island (seriously, there's ''no one'' there) should do the trick well enough.
** It's not like where it was hidden wasn't already secure, simply because no one knew where to look. It's not like Davy left an 'X' marking the spot or had it near some identifiable landmark. The only people who even knew where he specifically buried it were Jones himself and maybe some of his crew. In fact, if not for the magic compass that was probably crafted by the same Goddess who gave Jones his power, no one would have ever found it.

* Are Jack and Barbossa friends?
** They're enemies who respect one another and are willing to team up whenever something that threatens both of them comes down the pipe, so they can go back to their private feuding in peace.
** That seems logical. They were as close to being friends as two pirates of their sort could be.
** They were definitely enemies in the first film, but it appears that Jack's killing Barbossa (even temporarily) has settled the score. In the scene beside the dead Kraken, they recognize their common situation (being pirates in a world they don't entirely fit into anymore), so by OST they've become VitriolicBestBuds... or at least frenemies.

* The ''Flying Dutchman'' can go underwater. Yet when she surfaces (as demonstrated early in the third movie) she can immediately start to fire her cannons. How do they keep the powder dry?
** Same way the ship doesn't sink? Voodoo magic.
** The Dutchman is pretty clearly magical down to its keel, anyway- we ''are'' talking a ship that was made for the express purpose of ''sailing souls to the afterlife'', after all. None of its abilities should be that surprising, nor need much of an explanation beyond [[AWizardDidIt Davy Jones Did It]].

* Elizabeth's fighting skills. She goes all the way from damsel in distress in the beginning of the first movie to holding her own with a cutlass against multiple crew members of the Flying Dutchman in the second to being on par with any main character in the third in terms of fencing. Where did that all come from exactly? Did she start practicing fencing for three hours a day?
** She says that Will taught her how to handle a sword, so whose to say he didn't put her on his own training regimen? Besides, she already acquitted herself pretty well in the FinalBattle in ''Curse of the Black Pearl'', so it's not like she was completely helpless before.

* What kind of a lord is Lord Beckett? He's referred to either as Lord Beckett or Lord Cutler Beckett. According to [[https://en.wikipedia.org/wiki/Courtesy_titles_in_the_United_Kingdom this,]] the form "Lord first name last name" is reserved for younger sons of Dukes and Marquesses, so Beckett could only be officially called "Lord Cutler Beckett" if his father was made a Duke or Marquess and he was the younger son. And even then, it is simply a courtesy title based on his relationship to an actual title holder and has no legal standing. By all accounts, Beckett holds his title in his own right, and according to [[https://en.wikipedia.org/wiki/Forms_of_address_in_the_United_Kingdom this,]] all peers below Duke are allowed to use the system "Lord Title" but mainly just barons use the form lord. So assuming that Beckett was created a baron, his official title would presumably be "Cutler Beckett, 1st Baron Beckett" shortened to "Lord Beckett" in colloquial use, with the Beckett being derived from his title and not his surname, although they may be the same. He wouldn't however be called "Lord Cutler Beckett". So why is he called that?
** His introductory scene in ''Dead Man's Chest'' hints "Lord Beckett" is the correct form and he was recently awarded some form of nobility. Swan refers to him as "Beckett?" and he responds with "It's ''Lord'' Beckett now." The way he gloats about it implies he was made nobility recently and by his own merits (rather than his father becoming a duke), so this gives credence to the idea of him being recently made a Baron. The only characters who refer to him as "Lord Cutler Beckett" are his enemies (usually Barbossa, like at the Shipwreck Cove speech), who have no reason to give half a damn about how his title is to be said. The man himself and his henchmen always seem to refer to him as "Lord Beckett!"
*** Or that his father, the previous baron, up and died recently and Cutler was the eldest son. Simple inheritance is how most such titles are acquired, and if we assume Tom Hollander is the same age as his character then Cutler's father would be somewhat elderly.
*** For what it's worth, the letter of marque he gives is signed "Lord Cutler Beckett".
** Somewhat related to the above point, what exactly gives Beckett the authority to stroll into the Caribbean, start ordering everyone around, including Admirals, and even order executions? He's a Lord, but does that really come with carte-blanche authority over any territory he happens to fancy? For a while, he's blackmailing Swann, who holds the actual post of Governor, into putting his signature on Beckett's orders. ''That'' makes perfect sense. But after Swann is killed, how does Beckett keep making enforceable orders? What's his post supposed to be?
** By then, his post is, "I have the most money, the most guns, and an invincible, unstoppable immortal enforcer on my payroll, listen to me or you die."
** One of those orders Beckett coerced Swann into signing was probably an order designating Beckett as the Governor's provisional successor. In the event of Swann's death (which Beckett eventually arranged, but it ''could'' have happened naturally) - Swann was an older gentleman and the Caribbean was rife with disease back then. So he'd ''need'' a designated successor to run things until the King could formally appoint and send a replacement. Which never happened, as word of Swann's death was most likely "lost in transit" on its way back to England... if indeed Beckett even told anyone the rightful Governor was dead and not "indisposed" from malaria or whatever.

* This one is about the ride: The skeleton in bed and the skeleton on the pile of Treasure. How did they die in those positions? Usually when you die your body goes limp, but they're in positions that would be impossible for a dead person to hold. How did they get this way? There's no evidence someone came along and did that to them either; no ropes or supports are keeping them in position, the skeletons are literally just in those positions.

* Did the ''Flying Dutchman'' receive, for lack of a better word, "upgrades" to her appearance and propulsion methods once the "[[WoodenShipsAndIronMen Age Of Sail]]" ended? Is she now a nuclear submarine or aircraft carrier or some such, or still a sailing ship?
** It's entirely possible the age of sail [[MedievalStasis never ended]] in Pirates of the Caribbean: the conflict of the second and third movies seems to be about the end of the Age of Discovery and the world setting into the pace it acquired in the 19th century of a globalized nature with no "blank spots on the map", but by the end of the third it is shown pretty unambiguously that the heroes squashed that process. As for "IRL", the sightings of the Dutchman (the latest high profile ones being from the 1940s) seem to always include it being a age of sail-ish vessel decked out in full masts, so it seems like the Dutchman can hold its own fine through the ages. It is magic, after all.

* Why didn't Jack (Sparrow) take another Aztec coin after the curse was broken? Besides getting the Black Pearl back, Jack's main goal throughout the franchise is to become immortal. Isn't that part of the reason why he was trying to find Isla de Muerta in the first place?
** Jack also likes to indulge himself with pleasures of the flesh and have fun, he doesn't want to be an immortal rotting skeleton who cannot taste or feel. Not to mention that immortality doesn't seem to be something he has thought about prior to Davy Jones wanting his very immediate death, and soul in servitude, in the 2nd movie.
** Also, when he was trying to find Isla de Muerta the first time, he wasn't actually ''aware'' of the curse (or at least was probably more willing to brush it off). None of them were. Seeing what the curse did probably led him to reconsider any plans on using the gold to become immortal since, let's face it, it's not a particularly pleasant form of immortality.
** As Jack said in the third film "Death has a way of reshuffling one's priorities." He was never particularly interested in immortality, and in fact, he didn't even know what he wanted, given how his compass wasn't working in the second film. He only reconsiders becoming immortal after dying, and that's because he knew what awaited him after death and he didn't want to go back.

* WordOfGod says that in the first movie, Will is the best swordsman, Norrington and Barbossa are tied for second place, and Jack is the worst. How is someone who practices with non-moving objects a better swordsman than a seasoned pirate and a veteran officer of the Royal Navy?
** Will is ''mechanically'' the best swordsman, but how often does he actually win his fights (when not up against {{mooks}})? Besides, it's entirely possible he has a sparring partner (or more than one) and we just don't see them because this person/people is ultimately irrelevant to the story.
** He would've beaten Jack if Jack hadn't cheated - as both of them understood. He never actually fights either Barbossa or Norrington except for against Norrington and Jack in the threeway duel in the second film, so no direct comparisons are possible. About a possible sparring partner: it would stand to reason that his partner/s would be of equal skill with a blade, so wouldn't Will have wanted to bring him along? Besides, the way people interact with him makes it seem like nobody really gives two copper pieces about Will, so it's doubtful that anyone was willing to spar three hours a day with him.
** The navy and the local government don’t care much about him. That’s not to say he wouldn’t have friends amongst his peers in the port who did care enough to help him as a sparring partner.
** You make the exact point; Jack cheats. So will just about everybody else. Will falls for that sort of thing. That makes them, effectively, more dangerous than Will, even if he'd beat them in a fair duel where everyone had to follow the rules. The audience knows nothing about Will's training other than that he does it, so such a sparring partner is hypothetical at best.
** How do we know Will only practices against non-moving objects? We've never actually seen him practice.
** Will is a ''blacksmith''. Practice or no practice, he's probably a lot ''stronger'' than (lazy) Jack or (upper-crust) Norrington, simply because he's spent so many years pounding on hot metal with hammers. Barbossa might be in Will's league in terms of muscle-power, but he's somewhat older than the others and perhaps tires faster when he's not being undead.
** THIS flimsy-looking refined boy is an accomplished blacksmith? Really? In the beginning of the movie, when Will delivers the sword, and the governor asks him to "pass his compliments on to the master", the confusion makes sense - he looked like a delivery boy, not a craftsman.
** Actually [[Literature/UnseenAcademicals Mr. Nutt]] explains that one- your typical blacksmith is as likely to be 'wiry' as a big guy. MusclesAreMeaningless does have some real-life basis. As for the 'refined' bit... well, he has mixed with his betters quite a bit, and Will at this stage comes across as a guy who feels more comfortable where there are rules to follow.
** The "compliments to your master" bit was because Governor Swann knew Will was an ''apprentice'', you know, a student. He didn't think Will was advanced enough to create such a masterpiece.
** "Jack is the worst swordsman" seems more like an InformedFlaw on the part of WordOfGod. He loses a grand total of ''one'' fair duel in the entire trilogy: the one against Will. The second fight he loses is a MeleeATrois against Will and Norrington, one of those being the guy who defeated him before and the other being a former Royal Navy commodore. The ''other'' one-on-one duel Jack fights in the trilogy is against Davy Jones, whom he actually is able to ''disarm'' and only winds up "losing" because Jones grabbed his sword and snapped it in two when Jack went for the killing blow.
** He had the advantage against Jones because they were fighting on top of the ship's yardarm, and Jones has a spike leg.
** It's not that Jack's a ''bad'' swordsman, it's that he's the worst swordsman out of a group of four ''very'' good swordsmen. Also, that WordOfGod is about the ''first'' movie. Jack may well have improved quite a bit since then.
** It's possible that he is the "worst" swordsman in terms of technical skill. Jack's ability to handle himself in sword fights is due to his skill in taking advantage of his surroundings and improvising (or as Will would put it, cheating).
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