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.
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)
Awesomely called back in the third film. Jack appears on the mast of the Pearl, riding his ship across a desert. Made absolutely priceless as, just as the ship enters the water and the awesome music fades:
Ragetti: (shakily points at the Pearl) ...boat...
Just watch anytime Jack Sparrow tries to talk to a woman.
Especially when they discover the first mate among the crew:
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?
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!
The best part of the above is when Jack picks up his pistol - the one with the single shot he was saving for Barbossa - and almost shoots Elizabeth.
And before that.
Elizabeth: So that's it, then. That's the secret, grand adventure of the infamous Jack Sparrow. You spent three days lying on a beach, drinking rum. Jack: Welcome to the Caribbean, love.
Barbossa's expression as Jack alludes to him not wanting to kill Will and lift the curse. It just says it all, he doesn't want to listen and is likely going to regret it, but he just has to find out what Jack means.
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: You'll have to forgive him sir. Cotton here's a mute; 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.
The list of Jack's crimes as he's about to be executed, including "impersonating a clergyman of the Church of England", which elicits a wry grin from a reminiscing Jack.
"STOP BLOWIN' HOLES IN MY 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.
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 Captain 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 scene where the kebab!Jack falls through the bridges. Especially when the tribeswomen just watch for a second, one basically says "Eh, whatever," then they walk away, as if it happens ALL the time.
The swordfight on Isla Cruces. It's not the fight, it's Elizabeth's reaction to it. She even walks sarcastically.
Elizabeth: This is barbaric! This is no way for grown men to settle...Oh, FINE! Let's just...haul out our swords and start banging away at each other, that will solve EVERYTHING! I'VE HAD IT! I'VE HAD IT WITH WOBBLY-LEGGED...RUM-SOAKED...PIRATES!
Made especially hilarious with the audio commentary: According to the writers, everything was going great that day. Then came Keira, sweet little Keira having an absolute MELTDOWN.
The part where three pirates are trying to have an honest-to-goodness swordfight on a moving water wheel.
The one where the wheel falls over, Will and Norrington stumble out, and Will tries to rush over to Liz and help her...and he's too dizzy to even walk properly.
And then there's when Jack is on the inside of the water wheel, grabs the key, and gets a triumphant look on his face...right before a metal bar smacks him in the head, knocking him out of it.
And of course, the part where Ragetti, Pintel, and Elizabeth abruptly pause their battle just to stare blankly as the wheel rolls past them, then once it's off-screen they shrug and return to the battle as though nothing had happened.
One of Davy Jones' crew mates is running with the chest, when Jack throws a coconut and knocks his head off. The head shouts directions to the blind body (about 2 minutes in).
Hadras: Aiyaaa. Anido. Anido! Follow my voice, follow my voice. To the left... no, turn around. Go to the right. Go -
(the body rams against a tree)
Hadras: ...No, that's a tree.
Jack: Oh, shut it.
A little while later, Norrington makes a run for it with the Dead Man's Chest in tow and the crew of the Dutchman in hot pursuit, only to be brought up short by Hadras, who's currently holding his severed head under his arm. After a tense standoff, Norrington simply tosses the Chest at Hadras- who drops his head to grab it - and runs for it; then, Hadras' body and the other crewmembers stroll off, leaving the very annoyed head shouting after them; eventually, it mutters, "Pirates!" then sprouts crab legs to follow them with, grumbling irritably to itself.
Will: What about Jack? I'm not leaving without him!
Jack:(Being chased by cannibals) AHHHHHHHHHHHHHHHHHHHHH!
The part where the crew are trying to scare off the Kraken, only to discover they're short on gunpowder. Will tells them to bring up the rum, and all the crew stop dead in their tracks. After a moment, Gibbs (reluctantly) agrees, and starts crying afterwards...
The 'three people, two swords' scene at Isla Cruces, right after Elizabeth's freakout (mentioned above). She notices Pintel and Ragetti trying to make off with the chest during the Mêlée à Trois going on between Jack, Will, and Norrington. She chases after them, and when they meet in the forest, she tries to pull out her sword to fight...only to realize that Will, who had arrived unarmed, yanked her sword in order to fight. The awkward Oh Crap smile she gives Pintel and Ragetti is priceless.
The pirates trying to swing the cages to the cliffs.
Made even more hilarious with the background music being something one would hear at a carnival.
The scene where Will, Beckett and Davy Jones are having that little tea party is amusing. Just think about it: A Cthulhu-look-a-like pirate captain, blacksmith turned pirate and an evil lord having a nice and tranquil teatime while trying to betray and kill each others. Ladies and gentlemen, welcome to theMind Screw. It's such a surreal situation all by itself that it has its own comedic value.
"Did no one come to save me just because they missed me?"
Cue his actual crew, all bit players most of the time, slowly raising their hands, starting with the midget pirate with no lines.
Jack: What are YOU doing...The captain gives orders on the ship.
Barbossa: The captain of this ship is giving orders.
Jack: My ship, makes me captain!
Barbossa: They be my charts.
Jack: Well, that makes you...chartman!
And after that, Pintel steps in:
Pintel: STOW IT! THE BOTH OF YOU! THAT'S AN ORDER! UNDERSTAND?! (Jack and Barbossa stare at him in surprise) ...Sorry, I just thought with the captain issue in doubt I'd throw in my name for consideration.
What makes it funnier is that after Pintel snaps at them, EVERYONE on deck stops and stares at him.
Arguably followed by a rather Heartwarming moment after Pintel has backed out of the fight:
Ragetti: I'd vote for you.
After failed Mexican Stand Off, "We can still use them as clubs!" (gets bonked over the head with a gun)
Don't forget the lead-in to the failure: Everyone points their pistols at everyone else... then they all start laughing... and then they point their pistols at each other again.
After Jack fires at Barbossa in that scene, Barbossa gives him a look like "You were actually going to shoot me!"
The Monkey pulls a pistol on the Parrot, which responds...
Jack is swinging around the Pearl and the Dutchman on a rope, then comes face-to-face with one of Jones' crew. He looks at the guy's belt, noticing something.
Jack: Oy! (grabs pistol out of guy's belt) My pistol! (hits guy over the head)
Jack's incredibly long, detailed, and round-about way of voting during the Pirate Council:
Jack: Cuttlefish. Eh? Let us not, dear friends, forget our dear friends the cuttlefish. Flipping glorious little sausages. Pen them up together, and they will devour each other without a second thought. Human nature, innit? Ooor... fish nature. So, yes... we could hold up here, well-provisioned and well-armed, and half of us would be dead within the month - which seems grim to me any way you slice it! Or, ahh, as my learned colleague so naively suggests, we can release Calypso, and we can pray that she will be merciful. I rather doubt it. Can we, in fact, pretend that she is anything other than a woman scorned, like which fury Hell hath none? We cannot. Res ipsa loquitur, tabula in naufragio, we are left with but one option. I agree with, and I cannot believe the words are coming out of me mouth... Captain Swann. We must fight.
This exchange follows right after that speech.
Barbossa: You've always run away from a fight!
Jack: Have not.
Barbossa: You have so.
Jack: Have not.
Barbossa: You have so!
Jack: Have not!
Barbossa: You have so and you know it!
Jack: Have not! Slander and calumny! I have only ever embraced that oldest and noblest of pirate traditions. I submit that here now, that is what we all must do. We must fight, to run away.
When Barbosa and Elizabeth go to Singapore, they are ordered to leave all their weapons with other pirates to gain entry to Sao Feng's hideout. Elizabeth removes a large amount of hidden weapons, including a rather large gun that by all rights, shouldn't fit anywhere... comfortably. If you look closely during that scene, you'll see Barbossa look behind her with a rather confused/surprised expression.
After coming upon Shipwreck Island, which contains Shipwreck Cove, and the town of Shipwreck, Jack realizes how unimaginative pirates are at naming things.
Jack: I once sailed with a geezer what lost both his arms and part of his eye.
Gibbs: What did you call him?
The "Up Is Down" scene. Nearly everyone confused, but still following Jack, while Barbossa just stands there watching everyone (until he realizes what Jack is up to).
Jack's escape from the Endeavour to the Pearl with a rope tied to a cannon. For added funny, he sticks a tiny figurine of Beckett inside the cannon.
And then after seeing him go sailing through the air, his crew members start looking for him in the water, only for Barbossa to do a hilarious Double Take when he sees Jack standing neatly on the Pearl's stern.
Jack: And that was without a single drop of rum!
Don't forget Becket asking how long it'll take for them to be ready to pursue, and is answered by the cracking of the main mast as it falls over from the cannon blast. He doesn't even turn. And then the Lampshade Hanging.
Made funnier by the fact that they had been arguing about who was captain just days(?) before. And later, when they're brought back on the boat, Jack is hiding behind Barbossa.
Jack proudly saying that he has the key to Davy Jones' chest. Jones then raises the key himself and says "No, you don't!"
During their fight, Jack and Davy Jones are trying to escape by running around a capstan. Jones suddenly gets a look of "Wait a minute... I'm going to try something else," and proceeds to force himself into the capstan. Jack's response? Spin it around while Jones flails in confusion! Unfortunately, when it stops spinning... Jones is face-to-face with Jack. Whoops.
A blink-and-you'll-miss-it one, but the Parley just before the final battle has the two sides meet on a small island, this includes Davy Jones who can't set foot on land, so he has to stand in a bucket of water and there are several smaller buckets leading back to the water.
There's also the scene with the Brethren Court where, after Jack votes Elizabeth be 'king' of the Brethren Court, everyone voices their disagreement.
Jack: Am I to understand that you lot will not be keeping to the code, then?
(Teague breaks a guitar string and bestows a Death Glare on the entire Brethren Court- everyone goes silent)
Jack's disgust when he sees Will using dead bodies to form a Trail Of Breadcrumbs, especially when he learns that this is the result of Will "thinking like Jack."
Jack: And this is what you came up with?
Maelstrom! Elizabeth's immediate reaction? "Captain Barbossa! We need you at the helm!" Crosses over into Heartwarming when you contrast it with her reaction to the waterfall earlier.
Murtogg and Mullroy turning up after the final battle on the Pearl, disguised as pirates and spouting off cliche pirate phrases. Pintel and Ragetti take one look at them, decide "What the hell", and go along with it.
On Stranger Tides
After Jack's failed mutiny:
Jack: Captain, I wish to report a mutiny. I can name fingers and point names.
Jack's long, Big "NO!"-ish scream when a voodoo doll of him is thrown off a cliff, leading into a slightly embarrassed silence when nothing bad happens to him.
Then, he actually does jump, and his scream sounds exactly the same.
Angelica near the start to Jack:
Angelica: I was innocent of the ways of men!
Jack: You displayed quite a lot of technique for someone I supposedly corrupted.
While discussing the circumstances of their first meeting:
Angelica: What were you doing in a Spanish convent anyway?
Jack: I mistook it for a brothel- it was an honest mistake!
Which is a nice Viewers Are Geniuses moment; that was still the era where "a nunnery" more properly referred to a whorehouse.
And just after that:
Angelica: *surrounded by red coats* We are at a disadvantage.
Jack: Speak for yerself. Unlike some who pretend to be, but cannot in fact hold a candle to, I am Captain Jack Sparrow. *proceeds to slash open beer barrels, creating distraction, then stops to drink from an opened wine barrel*
Jack trying to lock Angelica in her cabin so she'll be safe. It... doesn't work out too well.
Angelica: "Sparrow! Ven aquí o te arranco la cabeza!" (Translated: "Sparrow! Get back here or I'll cut off your head!")
She then wings her sword into (and through) the door so the tip ends up about an inch from Jack's face. Nice Ironic Echo to Will throwing his sword into the smithy's door beside Jack's face in the first movie!
"Someone make note of that man's bravery."
"Well, Your Heiney...."
The whole scene with the king, really.
Jack in the judge's wig. Reminds one of how Jack was being charged with "impersonating a member of the clergy" that one time.
Jack realizing that the Ponce de Leon really wants to keep his map.
Bonus points for Barbossa clearly mouthing "Don't touch the map!" Something about Rush's expression is hilarious.
Jack is running off to find Ponce de Leon's ship. Then he trips over some plants and falls out of sight. Then he stands up and starts stabbing the plants with his sword.
Better yet, that was improvised by Depp.
During the climax, just as Barbossa's and Blackbeard's crews are about to start fighting, Jack interrupts and states that it's foolish for the two crews to kill each other over Barbossa's grudge against Blackbeard, so they should just sit back and let the two captains duke it out personally. There's silence, and then one of the Blackbeard pirates nods in agreement and sheathes his sword... and then everyone fights anyway.
When Jack and another pirate are freeing Philip during the mutiny:
Barbossa makes a metaphor about his footsteps in sand to describe why he can't turn back... then his jackass second-in-command feels the need to point out that it would technically be "footstep" on account of his infirmity. Barbossa's expression is priceless.
Something about Jack's expression after claiming that it's not Blackbeard's ship and they have been deceived, only for another pirate to feel the need to reply "We are decepted then", is simply hilarious.
During the mutiny, when Angelica is half-awake;
Angelica: Jack, if this is a dream, then you can keep the sword and boots on. If it's not...
Jack: It's a dream!
When Jack and the crew are planning the mutiny:
Jack: Blackbeard. What are his habits?
Scrum: Stays mostly to his cabin.
Crew: That's right, mostly to his cabin.
Jack: Yes, but when he comes out.
Kid: He don't really come out.
Crew: (mumbles in agreement)
Jack: He must come out sometime.
Crew: Not really, no. (mumbling in agreement)
Jack: Any of you sail with him before?
Crew: "No, no." "I've never." "Definitely not."
Jack: Any of you seen him before?
Crew: Not really, no. (mumbles some more)
Later in the scene...
Jack: Gentlemen, you have all been monstrously decieved.
"Mr. Cotton! Do you have the courage and fortitude to follow orders and stay true in the face of danger and almost certain death?!"
Jack: Do you have the courage and fortitude to follow orders and stay...I love you man, let's just face the fact.
Jack: Do you have the courage to fortitude...
Jack: Do you have the courage and fortitude to follow orders and stay brave in the sea...oh, god, I hate this bloody line. Where are the writers? I'm gonna kill them...
Not to mention, he said all of that last bit in character.
On the deck after rescuing Elizabeth, Norrington is mocking Jack's equipment and then suddenly...
Johnny Depp: Was that a plane?
At the Pirate Council:
Johnny Depp: "Let us not, dear friends, forget our... lines. Yes! Let us not forget our lines."
Johnny Depp forgetting the name of the Flying Dutchman and calling it The Davy Jones Crocodile Machine.
There's also Orlando Bloom's "Aarrrr, swash swash, buckle buckle," and Tom Hollander and Johnny Depp's numerous tries to get a scene done (the bargain upon the Endeavour), which includes Hollander's haughty "I'm trying to work here," and Depp's "That be...You can't curse on a Disney film, mate. *pause in which the director confirms* ...see, I told you!"
Context for the repeated failed shots: Hollander and Beckett are filming the scene with a foghorn outside. It's so loud and close by that when it goes off, it nearly knocks both of them off their feet. Of course, this happens more than once...
Hollander doing an impromptu jig while filming a scene.
One take of the otherwise dramatic opening scene in Dead Man's Chest:
(Beckett) *long beat, points* "Kill him!"
(Governor Swann) "The charge is conspiring to set free a man convicted of...*takes a sigh with a long beat* ...I can't read my own writing. Crimes! Thank you very much!" (If you look closely, you can also see Tom Hollander (Beckett) struggling not to crack up.)
This one ties into Governor Swann's above quote:
Beckett: The charges are conspiring to set free a man legally... lawfully... Sorry, I'm slightly confused because I didn't know which verse we were doing. Shall I say it or Jonathon (Governor Swann) say it?"
Governor Swann: It's my line, dear.
Governor Swann: It's alright. (Jokingly mimes while shaking his fist at Beckett: I'm going to f-ing kill you, you f-ing b*stard...)
Jack's conditions of help: "I shall help you to find the compass, if you'll do strange things to my dog. His name is Tim."
Geoffrey Rush staying in character when he flubs his lines:
"Calypso! I come before you as but a servant... *his hat is blown off* Ye blew my hat off, ye *bleep*!"
"And I won't let the likes of Beckett Cutler... *pause* er, sometimes known as Cutler Beckett..."
Will: *yells an order to the crew.* Barbossa: "NAY BELAY THAT!" * long beat* "...DO SOMETHING ELSE!"
Geoffrey Rush accidentally hitting himself in the eye with his spyglass is known to cause giggles and sympathetic wincing at the same time.
In another outtake, Depp is shooting the Locker scene where he swings from the Pearl onto the desert below. He preps, swings, the camera follows, and crash; Depp crashes onto the ground, having mistimed his landing.
Johnny Depp: *under his breath* "Oh, my god..." *gets right to his feet completely in-character*
During the Parlay scene from At World's End, as Geoffrey Rush, Keira Knightley, and Johnny Depp are walking, Rush's hat flies off due to the wind. What does Depp do? Staying perfectly in the character of Jack Sparrow, he tosses his own hat off and strikes a dramatic pose.
Helicopters keep interrupting during On Stranger Tides
Johnny: What I want first...is Ponce de Leon's helicopter.
Scrum: ...or when an helicopter flies over your head, and you're supposed to be in the middle of a scene. It's not real.
Extra: It screws everything.
"I'm Peter Pan!"
Even funnier if you've played Kingdom Hearts 2. Due to the lack of a Neverland level in that game, Sora gets the Peter Pan/Tinkerbell summon in Port Royal instead.
Johnny's numerous attempts to get the hat off Penelope's head.
Johnny: I think this take's going very well, don't you?
Rush attempting to get his wooden leg back on.
Rush: No, it's broken.
Depp: Can't help you, mate. I don't want to touch it.
The best part: both say this in character.
"God, stop it, please!"
On Stranger Tides: Johnny appears from round the corner...with his hat on wonky. He notices, straightens it before backing out of the scene.
Deleted Scene from AWE. Barbossa and Jack are fighting (like children) over who gets to steer the ship. They even go so far as to wrestle over the wheel. Even more so when it's revealed that they've split captaincy of the ship between them...by sides.