Jack climbs a fence while drunk out of his mind, and falls into mud (the visual is hilarious - he basically goes from vertical to horizontal in about half a second). Then he enters a tavern and drinks from his bottle of rum (which is also covered in mud), and doesn't seem remotely bothered.
Just as he falls, you can hear him mutter 'bugger!' under his breath.
Before that, Jack mumbling that he hasn't had a (figurative) wash in years, while the rain is giving him a (literal) wash.
The mud has pigs in it. It's probably not just mud. Yep, he's landed in poop. No wonder it rained...
When Jack steps back outside, he tries to get a drink from the bottle, only for the bottle to get shot.
The brief Mood Whiplash with Salazar's "Will you say that to him, please?" to Henry after sparing his life and ordering him to deliver his message of doom to Jack Sparrow.
Jack and his crew have been reduced to riding a small pathetic ship called the Dying Gull.
Carina's Establishing Character Moment can count as this and a Moment of Awesome. She's in a jail cell, confessing that she's not a witch, confessing she's an educated woman, oh, and confessing that while talking to the priest, she picked the lock.
Granted it's a scene that walks alongside Nightmare Fuel, there's one part where an unsuspecting pirate on a ship takes a swig of water from a ladle, only to see one of Salazar's undead sea gull. The gull in question is missing pieces of itself, making it look like abstract art. Naturally, said-pirate splashes his face with water to make sure it's not a hallucination.
The Italian dub gains extra Double Entendre points, as stern is "Poppa", which sounds like the singular form of Poppe, a slang word for "boobs".
Turns out, despite being a pathetic little ship, the Dying Gull can indeed float. If it's any indication, Jack and his crew are ecstatic with overjoyed disbelief that it is capable of sailing.
After they set sail on the Dying Gull, Jack proceeds to threaten Carina that if she doesn't take them to Poseidon's Trident, he'll throw Henry overboard. They tie up and gag the poor guy, who struggles to mumble something to Carina. She tries to call Jack out on his bluff, but true to their word, they toss Henry overboard. ...Or so it would seem. Once Carina surrenders and promises to lead them, Jack and his crew reveal they merely tossed Henry onto a lifeboat just below them. And all along, that was what Henry was trying to tell Carina while he was gagged.
One of Salazar's men appears to be nothing but a floating hat.
One of the crewmates curiously puts his hand through the empty space where a head is supposed to be.
When the witch suggests Barbossa retires for his own safety, his response is disgust and disbelief at imagining himself retiring to the country, milking cows and making cheese.
The absolute disgust in his voice at the thought if grass just sells it.
Henry Turner is less than impressed to find the pirate of legends drunk and in a jail cell.
Henry: Do you even have a ship, crew... pants?? Jack: A great pirate does not require such intricacies.
Upon hearing that Henry is the offspring of Will and Elizabeth, Jack reveals that he still harbors feelings for her and asks Henry if his mother talks about him, only for Henry to reveal that Elizabeth never even mentioned or cared for him. This comes as an absolute shock to Jack. Bonus points for Jack referring to Will as a eunuch, again.
Jack: Does mommy ever ask about me?
Henry: (with a straight face) No.
Then Jack falls asleep mid-conversation.
Jack:(slurring heavily) I'm so sorry, were you still talking?
Henry reminds us of the time period the films take place in after watching Carina undress to escape into the ocean:
Carina:(while running for her life with Jack) I'm not looking for trouble. Jack:(disapproving) What a horrible way to live!
Barbossa relating what he knows of Salazar, only for the man himself to correct him on one certain detail...
Barbossa: I have heard stories of the mighty Spanish captain, who's hunted and killed thousands of men...
Salazar: No, no, no, no! Men, no! No, no, no, no... pirates!
When Salazar recounts how young Jack Sparrow ruined his life, he recalls how the young pirate called out to him from the ship's crows nest "like a birdy". And that is how Captain Jack Sparrow got his name.
Granted there's rage and vengefulness behind his words, it's too cute and too funny how Salazar keeps pronouncing "Sparrow". Especially when meeting Jack all these years, he says it like he were cooing at a little pet canary in a cage rather than a hated rival he's hunted for.
Jack is inside a large safe the announcer just mentioned nobody could break into. He's not only drunk enough to not remember he's stealing the safe, but also not remember just who he did the night before, who is still inside the safe with him.
Which then leads to the lead officer ordering to fire on Jack, forgo the woman. That woman is his wife, as noted by the announcer.
Jack: Does anyone remember why I'm here? [...] Oh, yes, I'm robbin' the bank!
The fact that a bank robbery turns into the entire building being dragged away ("Have you seen my bank?"). And once it's over, the entire safe is empty aside from a single coin.
When his crew come in to save him, they fire a cannonball at the guillotine stand as the blade is dropped. The supports under the guillotine are destroyed, it spins upside down, and the blade goes away from his head. However, the whole thing spins around like a yo-yo for several moments afterwards, with the blade continuously dropping towards Jack and then falling backwards. Jack doesn't look at all pleased with the situation.
Jack finally gets free of his restraints, only for the guillotine's blade to land so close in front of him.
The irony is that the guillotine was proposed as a painless and humane way to execute somebody - previous execution methods were often extremely slow and painful; even the ones that weren't meant to torture (like the Breaking Wheel). Executioners with axes were often sloppy, taking several blows to sever the neck, and a hanging could take several minutes. A guillotine's rope could be handed into the crowd or even tied to an animal.
Jack lands groin-first onto a cannon when the Silent Mary attacks the Black Pearl, but Jack's "ow" is more in line with stubbing one's toe.
Hilarious in Hindsight: It seems Carina takes after Barbossa's tendency to argue with Jack. In fact, Barbossa and Jack argued in the same tennis-court-match manner in the Third movie.
Second time watching it, it's strangely funny that Carina slapped Barbossa for speaking poorly of her father's "good name". In the very first movie, Barbossa back-handed Elizabeth (for impersonating as Bill Turner's flesh-and-blood). Now he's just been slapped by his own daughter, as though by some strange working of karma. What really sells it is (blink and you'll miss) when he gives a little smile, as though thinking "Not the first time I've been slapped."
The whole part where Jack is roped into a Shotgun Wedding. Henry attempts to lawyer Jack out of it, but Jack ends up saying "I do." To the question of whether any man objects to the marriage, mind, but it's taken as the "I do".
Barbossa crashing the wedding. Jack asks if he brought a wedding present. Barbossa shoots the bride's brother who staged the shotgun wedding. Jack is satisfied with the "gift".
And Just before that scene? Jack was struggling to avoid kissing his would-be bride, and while their lips were just inches away from locking, Jack asks the bride if she likes sea food while looking like he's seconds away from throwing up.
Following that, he questions Barbossa if his leg "grew back" yet.
Someone attempts to shoot one of the undead pirates... and kills a friend because of the holey body.
Jack's final comment on the "revolting" sight of Will's reunion with Elizabeth, followed them and Henry and Carina kissing.
And this is after Jack almost got married to his abhorrent bride-to-be at the shotgun wedding.
When you think about it, Jack running whilst carrying the breaking bottle that contains the Black Pearl and yelling about how the Pearl was coming, is almost akin to a scene about others shouting how a woman is in the process of giving birth to a child. (Or a kid with his goldfish in a leaky bag, rushing to put it in a more suitable source of water.)
Jack:(believing the still-shrunken Pearl has sunk) She was a fine ship.
Facing death by pissed-off Salazar, Murtogg suggests he and Mulroy tell each other where they've stashed their treasure in case only one survives. Mulroy complies and gives directions to his buried loot... and only after he's finished does Murtogg confess he doesn't actually have any buried treasure.