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  • Barbossa's expression as Jack makes another ludicrously convoluted escape from trouble, this time in the middle of the court of King George II: his facial expression is a textbook example of "Oh, here we go *again*!" And just moments after he warned them all they were better off chaining Jack up...
    • Once again, Barbossa just looks bored as Jack's escaping.
  • 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: Mistook it for a brothel—honest mistake!
    • Which is a nice Viewers Are Geniuses moment; that was still the era where "a nunnery" more properly referred to a whorehouse.
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  • 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]
  • Philip tells Blackbeard to open Syrena's tank and let more air in. Jack agrees, saying "I support the missionary's position!"
  • Jack looking at the Black Pearl in a bottle... and then jumping back when Jack the Monkey pops up.
    Jack: He's even more annoying in miniature.
  • The Stinger at the end. Angelica is sulking by the tree, alone on an islet, when the Voodoo Doll of Jack washes up to shore. Cue devious smirk on her face. Poor Jackie. Poor, poor Jackie...
  • Jack and Angelica's faces moving closer... and the music suddenly stops when Jack bails out.
    Jack Sparrow: I gotta go.
  • Jack and Barbossa's raid on the Spanish camp.
    Jack: How's that escape plan workin'?
    Barbossa: Here's your chance to improvise.
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    • This is followed by Barbossa removing his peg leg to get to the secret compartment in it—which doesn't contain a sword, but rum.
      Jack: Oh, you've got a knife, that's very good.
      Barbossa: Better. [uncorks the flask]
      Jack: [pouting] I want one of those.
      • Which leads to a Heartwarming moment when Barbossa lets Jack have a drink.
  • What does Jack need for his plan to release the Black Pearl from its bottle?
    Jack: We shall need a crossbow, an hourglass, three goats, one of us must learn to play the trumpet, whilst the other one goes like this. [wiggles fingers]
    Gibbs: I know a man with a goat!
    Jack: Excellent. I can go like this. [wiggles fingers again]
    • Possible Call-Back: in the first movie, when Will is asking Gibbs about why Sparrow always behaves so strange, he makes a very similar gesture with the fingers.
  • Barbossa confronting Blackbeard: "Such crimes do include, but are not limited to, piracy, treason, murder, torture of the most heinous sort, including the brutal theft of one used, twisted, hairy right leg."
  • 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!Spanish 
    • 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!
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  • "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:
    Salaman: You're either with us, or against us!
    Philip: I'm not with you, neither am I against you.
    [beat]
    Salaman: Can he do that?
    Jack: He's religious, I believe it's required.
  • 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.
  • 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]
  • "Did everyone see that? Because I will NOT be doing it again!"
  • While traveling through the forest, Barbossa stops Gibbs and tells him not to let a frog sitting on his shoulder touch his skin. He reaches with tweezers to pick it off of Gibbs' shoulder, not because it's poisonous, but because collecting frogs happens to be his hobby. (He really is using them for poison, but the delivery is the funny part.)
    • Also leads into some Hypocritical Humor when he shouts at his men for stopping.
      Barbossa: You can sleep when you're dead. Push on!
  • In the cave to the Fountain of Youth, the stalactites are low enough that one crewman is able to touch it with his hands. When he snaps off the tip, another stalactite falls from the roof and kills another crew member. The Quartermaster insists that "We must not stop" as the crewman awkwardly tosses his snapped-off piece to the ground.
  • At the end when Jack maroons Angelica on a small island with the traditional pistol with one shot, there are several hilarious moments as she tries to get out of it:
    Angelica: [tied up] And how will I get free of these bonds?!
    Jack: [walking away not looking back] You broke free of your bonds half an hour ago, waiting for the exact moment to pounce! (Jack instinctively whirls round to stop Angelica whacking him in the head with a big stick)
    • And again she tries:
    Angelica: Admit it, Jack, you still love me!
    • Her last ditch attempt to convince Jack is particularly hilarious:
    Angelica: Wait! I am with child! Yours! (Beat)
    Jack: I don't recall that we ever had...
    Angelica: You were drunk!
    Jack: I've never actually been that drunk.

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