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  • Jack Sparrow's entrance into Port Royal, standing proudly atop the mast of his ship... which is mostly underwater as he enters the port, and sinks completely just as he casually walks on the dock.
    • Made all the more funny by the fact that at that moment, the music is blaring the main heroic theme, and not playing to the sheer ridiculousness of it.
    • Even better is that the audience is led on to thinking he's standing proudly on an actual ship...only to be revealed to be a dinghy with a sail that's got a leak. That honestly further accentuates the sinking moment above.
    • And, immediately afterwards, "Hold up there, you! It's a shilling to tie your boat up at the dock!" (cut to mast sticking out of the water next to the dock)
  • Anytime Jack Sparrow tries to talk to a woman.
    Jack: Scarlett!
    [SLAP]
    Jack: I'm not sure I deserved that...
    Jack: Giselle!
    Scarlett: Who was she?
    Jack: What?
    [SLAP]
    Jack: I may have deserved that...
    • Rule of Three comes into play when Jack recognizes one of the members of his new crew:
      Jack: Anamaria!
      [SLAP]
      Will: I suppose you didn't deserve that one either?
      Jack: No, that one I deserved.
  • During the final battle on Isla de Muerta, Will and Elizabeth skewer three undead pirates together, stuff a lit bomb into the middle one's empty ribcage, then push the three out of the moonlight, effectively trapping the bomb within the pirate's newly reformed flesh. The unfortunate fellow's "No fair!", followed by the ensuing explosion, was magnificent.
    • From the same scene:
    Elizabeth: Whose side is Jack on?
    Will: At the moment?
  • Will throws a sword at Jack; it pins in the door next to his face and Jack's eyes widen. You can just see him thinking. "I almost died."
    • Weaponless Will pulls a hot iron out of the fire to fight. The donkey lets out a little moan and tries to walk away because Jack had prodded the poor creature with the hot iron.
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  • The very beginning of the above scene: Jack and Barbossa are fighting in Isla de Muerta, Barbossa knocks Jack down and says "You can't beat me, Jack!". Jack then runs Barbossa through with his sword. Barbossa stabs Jack, who (unbeknownst to Barbossa) is cursed, and turns into a skeleton.
    Jack: [in skeleton form, examining his own hand] That's interesting... [starts walking the medallion across his fingers and grins at Barbossa] Couldn't resist, mate.
  • Barbossa lampshades he and Jack sword-fighting when neither of them are vulnerable to each other's blade:
    Barbossa: So what now, Jack Sparrow? Are we to be two immortals locked in an epic battle until Judgment Day and trumpets sound, hm?
    Jack: Or you could surrender.
  • And a few more blink-and-you'll-miss-it moments from that fight: Barbossa, pursuing Jack, slams face-first into a wall; Jack yells "Sorry!"
  • When Jack arrives at the treasure cave as Barbossa prepares to kill Will, the pirates are cheering. Then they slowly fall into silence as Jack politely pushes his way to the front, and Barbossa is left staring.
    Barbossa: It's not possible!
    Jack: Not probable.
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    • When Jack tells Barbossa he doesn't want to kill Will and then mutters "your funeral" and steps back, Barbossa rolls his eyes before asking what he means. It's an expression that says "I know I'm going to regret asking, but I have to..."
  • When Jack's crew steals the Pearl in the final battle.
    Ragetti: Is it supposed to be doing that?
    Pintel: They're stealing our ship!
    Ragetti: BLOODY PIRATES!
    • Especially hilarious since in the shot just prior, Elizabeth used the same phrase while rambling about the very same crew.
  • Jack convinces Barbossa to ally by promising to give him twenty-five percent of his plunder and a really big hat.
  • "BUT WHY IS THE RUM GONE?!?!"
    • The best part of the above is when Jack picks up his pistol—the one with the single shot that he was saving for Barbossa for ten years and almost shoots Elizabeth.
    • And before that:
      Elizabeth: So that's it, then. That's the secret, grand adventure of the infamous Captain Jack Sparrow. You spent three days lying on a beach, drinking rum.
      Jack: Welcome to the Caribbean, love.
    • "'Must have been terrible to be trapped here, Jack. Must have been terrible for you'—WELL IT BLOODY IS NOW!"
    • When Jack sees the Dauntless anchored off the island, having been attracted by the signal fire as Elizabeth claimed.
      Jack: There'll be no living with her after this.
  • This exchange, as Will is pulling a Stop, or I Shoot Myself!:
    Barbossa: Name your terms, Mr. Turner.
    Will: Elizabeth goes free!
    Barbossa: Yes. We know that one. Anything else?
  • This exchange:
    Jack Sparrow: Mr. Cotton! Do you have the courage and fortitude to follow orders and stay true in the face of danger and almost certain death?! [Cotton is silent] Mr. Cotton! Answer, man!
    Gibbs: He's a mute, sir; poor devil got his tongue cut out! So he's trained the parrot to talk for him. [beat] No one's yet figured how...
    Jack Sparrow: Mr. Cotton's... parrot! Same question.
    Cotton's Parrot: Awk! Wind in yer sails, wind in yer sails.
    Gibbs: Mostly we figure that means "yes".
    Jack Sparrow: Of course it does!
    • Jack is carrying a banana in this scene. This is never explained.
      • Perhaps it's just his breakfast.
      • It's actually bad luck to have a banana on a boat!
  • "Say goodbye!" *falling shop sign to the face* "...Goodbye."
  • "You will always remember this as the day that you almost caught Ca—" [slips]
  • In the attack on Port Royal, Will is confronted by a pirate:
    Jacoby: Hello! [Throws a bomb on the ground. It fails to explode. The pirate looks dejected. Will happily reaches for his sword. A second pirate runs past him.]
    Pirate 2: Outta my way, scum! [clubs Will on the head, knocking him out cold]
  • How Jack escaped from the island.
    Will: How did Jack get off the island?
    Gibbs: Well, I'll tell ya. He waded out into the shallows and he waited there three days and three nights, and all manner of sea creatures came, acclimating to his presence. And on the fourth morning, he roped himself a couple of sea turtles, lashed 'em together and made a raft.
    Will: (deadpan) He roped a couple of sea turtles.
    Gibbs: Ay, sea turtles.
    Will: What did he use for rope?
    Gibbs: Ah...
    Jack: Human hair. From my back.
  • Jack meeting Murtogg and Mullroy
    Jack: [Jack has just been ordered to explain why he's aboard the Interceptor and not to lie] Very well, I confess. It is my intention to commandeer one of these ships, pick up a crew in Tortuga, raid, pillage, plunder, and otherwise pilfer my weaselly black guts out.
    Murtogg: I said no lies!
    Mullroy: I think he's telling the truth...
    Murtogg: If he were telling the truth, he wouldn't have told us!
    • The next time we see them, the three are sitting down on the deck of the Interceptor, Murtogg and Mullroy listening in rapt attention as Jack tells them the story of one of his adventures. We don't see how the situation got to this point, which just makes it funnier.
  • The following:
    Barbossa: Why thank ye, Jack.
    Jack Sparrow: You're welcome.
    Barbossa: Not you. We named the monkey Jack.
    Monkey!Jack: :D
  • During Jack's execution, the herald announces him as "Jack Sparrow!" and Jack sighs and mutters "Captain! Captain Jack Sparrow!"
    • The list of Jack's crimes includes "impersonating a cleric of the Church of England", which elicits a wry grin from a reminiscing Jack. He then looks at the executioner with the same expression, as if expecting him to join in.
  • "STOP BLOWIN' HOLES IN MY SHIP!" Made even better by the fact that he's locked in the brig of "his" ship.
  • Will accidentally pulling one of the candle fixtures free, and quickly having to hide it when Governor Swann comes to see him.
  • After Will fumbles the romantic moment between him and Elizabeth after the battle is over:
    Jack Sparrow: If you were waiting for the opportune moment... that was it.
  • Governor Swann's fight with the skeleton arm—after he smashes it with a hammer for trying to steal his wig.
  • The Black Pearl crew back on Isla de Muerta the second time, getting all chanty, until Jack politely makes his way through the crowd, derailing what had been a dramatic moment the first time around.
    • Even better is the pirate's reaction to Jack being alive.
      Pirate: You're s'posed to be dead!
      Jack: [sounding genuinely confused] Am I not?
  • Pintel and Ragetti inform Elizabeth that if she doesn't agree to have dinner with Barbossa, she'll instead eat with the crew, naked. Intimidating on paper, but what makes it funny is they clearly think this might actually happen, and are sorely disappointed when she doesn't go for it.
  • Jack's response to Will's query about Elizabeth and basically summing up everyone's positions near the end of the movie:
    Captain Jack Sparrow: She's safe, just like I promised. She's all set to marry Norrington, just like she promised, and you get to die for her, just like you promised. So we're all men of our word, really. [beat] Except for Elizabeth, who is, in fact, a woman.
  • Elizabeth pulls a knife on Barbossa during dinner and stabs him in the chest with it. Barbossa (who is, at this point, immortal) calmly pulls it out, and then asks what Elizabeth was thinking doing such a thing.
    Barbossa: I'm curious. After killin' me, what was it you were plannin' on doin' next?
  • One scene in the movie has the heroes, out of cannon balls, loading their guns with bits and pieces of whatever they had at hand, including forks and knives. This was a Real Life practice, and such Abnormal Ammo was known as Langrage, used as a sort of improvised canister or grape shot.
    • The result of this is funny as well: Ragetti ends up with a fork in his (thankfully wooden) eye and the two look out the cannon port, which has an array of junk plastered around it.
    • One of the crew actually tosses Gibbs's flask into the cannon as well, despite his protests. When they fire on the Pearl, it winds up in Jack's cell, and he finds that it's empty. Then he returns it to Gibbs when he gets back to the Interceptor, who's mid-fight with a bunch of pirates. It's finding out that his flask is empty that really pisses Gibbs off.
  • When Norrington declares, "The ship is ours," after the pirates become mortal again, all the soldiers start cheering, "Huzzah!" Governor Swann joins in and as he does so, he wags his finger at a pirate and then mimes punching him.
  • "...And then they made me their chief."
    • Bonus points for how entranced the guards seem in his story.
  • Barbossa chucking the apple Jack handed him before being sent to the brig.
  • The scene where Pintel and Ragetti tell Will about his father and what they did to him is very dark and serious, and then they finish up. Keep in mind that up until this point Pintel had been very growly and serious:
    Pintel: [lightly] Course it was only after that we found out that we needed his blood to end the curse.
    Ragetti: That's what you call ironic.
    Pintel: [chuckles]
    • Also, during the story, Ragetti tries joining in, only for Pintel to yell "I'M TELLIN' THE STORY!" at him.
  • When Will is defending his attempt to save Jack from being hanged, Jack casually points to himself as he looks at the other guards, and smugly mouths the words 'that's me!'
  • After slicing Elizabeth's hand to try and lift the Aztec curse, Barbossa and his men wait a few seconds and then...nothing. The crew wonders what just happened and if it worked. Barbossa's solution? Whip out his pistol and shoot Pintel with it. Unsurprisingly, the other members of the crew attempt to mutiny against Barbossa because of his failure.
    Bo'sun: Did it work?
    Ragetti: I don't feel no different.
    Pintel: How do we tell?
    [Barbossa rolls his eyes and up and shoots Pintel where his heart should be; nothing happens]
    Bo'sun: You're not dead!
    Pintel: (chuckles) No! (Beat, and his face goes from happy to annoyed) He shot me!
    • And of course after building up that Elizabeth will be a blood sacrifice, Barbossa makes just one small cut on the palm of her hand. Elizabeth almost sounds disappointed.
    Elizabeth: That's it?
    Barbossa: Waste not.
  • When Jack and Will retrieve a sleeping Gibbs, Will tosses a bucket of water on him. After a brief exchange, Will throws another full bucket on him.
    Gibbs: BLAST! I'm already awake!
    Will: That was for the smell.
    • Then Gibbs just nods his head like "Okay, that's fair."
  • When Jack the monkey tries to scare Elizabeth for the second time, she is less than amused.
  • Jack tries to end on his dramatic line, but half way, he trips and falls off the ledge. He still was planning on escaping anyway. But that wasn't part of the plan. The fact that his face takes on an "Ohhh, shit!" look as he topples off the battlements.
  • When Elizabeth is having dinner with Barbossa, she tries to eat eloquently but when Barbossa tells her that she doesn't need to do that because there isn't anyone to impress. Elizabeth promptly drops her knife and fork and then gorges herself, while Barbossa looks on in surprise.
  • This exchange near the beginning:
    Elizabeth: Captain Barbossa, I am here to negotiate the cessation of hostilties against Port Royal.
    Barbossa: There are a lot of long words in there, miss—we're naught but humble pirates. What is it that you want?
    Elizabeth: I want you to leave and never come back.
    Elizabeth: (Stunned Silence)
    Barbossa: Means "no".
  • Elizabeth comes across a pirate threatening Will, who declares he's going to show him pain. Cue her thumping him over the head with what appears to be a golden stair banister, followed by saying that true pain is wearing a corset. "You like pain?" *wham!* Try wearing a corset!"
  • Jack getting hit by a bottle after his big sword fight with Will. As Johnny Depp keeps the same straight face when he falls over.

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