- When Flint, Gates, and Billy realize that Silver stole their logbook page, they go out to the ship to look for him. Silver, realizing they're on to him, tries to get on the launch carrying several of the crew from the ship to Nassau so he can disappear in the town. He's told that most of the men want to visit the brothel, and that he's last in line. Having no other choice, he jumps overboard, performing a tremendous belly-flop from at least fifteen feet in the air. Everyone, even Gates, winces in sympathy, and Silver himself screams in pain. Logan's response just sells it:
"That kid must really want to get laid."
- The exchange between Captain Naft and the appraiser, where the former is trying to convince the latter of the quality of a rather shoddy knockoff painting.
Naft: Fruit. Fruit. Tits. Tits. Plant. Plant. It's the fuckin' same!
- After a long and educated explanation of how they are not, in fact, the same, Naft starts in again with "Fruit, fruit. Tits, tits." Gates, watching the whole ordeal, just chuckles and says "I love this place."
- When Silver is watching Max get choked by Vane, he asks Idelle if she has a weapon, "A candlestick, or perhaps a heavy shoe." She hands him a machete. His response: his eyes light up and he tells her, "that'll do."
- The meeting between Vane and Flint in the third episode, where Gates keeps needing to take Flint outside to talk to him when he's undiplomatic. Vane even lampshades it:
"Are you as surprised as I am that I'm the only one here behaving myself?"
- When Billy takes over as Quartermaster, his very first task is trying to persuade the crew that, just this once, they should skip setting up the aptly named Fuck Tent. The next shot is of the crew pitching the tent.
- When Muldoon complains to Silver about how the pig that he "cooked" gave him the shits, Flint comes over, takes a bite, and declares the pig tastes fine. After Muldoon leaves, just as Silver is commenting that at least someone likes his cooking, Flint spits out the pig in disgust.
"What the fuck did you do to that?"
- When Vane is leaving to find a new crew after Eleanor's ban, Jack's attempts to get him to tell him his plans get increasingly desperate, going from calling him 'Captain' to 'Charles' and finally 'Chaz,' all with Vane completely ignoring him.
- When Jack and Anne are having sex, Jack's mind is on other things, so he goes limp, and angry, Anne huffs off, leaving him naked and tied to the bed. Then, in the distance, a donkey can be heard braying. In other words, the show itself is calling him a jackass.
- After agreeing to serve as Randall's caretaker, Silver comments that he believes that Randall is far more brilliant than the "half-wit" cook lets on. Randall's only response is to fart. Silver's dumbfounded expression absolutely sells the scene.
- The night before the Walrus crew finds the Urca, Flint and Gates spend an evening drinking together and reminiscing about the particularly unfortunate ex-crew member, Creg, who found a hidden bottle and, convinced it was fine liquor, took a huge swig without checking the contents. Which turned out to be piss. The moment is also a heartwarming moment for Flint, as he genuinely seems to be fond of his late crewman, and is one of the few times Flint is relaxed and has a happy smile on his face. It then becomes a heartbreaker, considering what Flint does to Gates the very next day.
- A subtle one, but watch Jack's face when he's firing Mrs. Mapleton for having her hand in the till. He's looking over her shoulder at Max for encouragement/guidance the whole time.
- John Silver's dawning horror that Flint's near suicidal plan for the Spanish Man o' War was not an elaborate escape ruse, and he fully intends to take the ship. To their credit, the two pull it off with only nearly dying and some bickering.
- And later, after they are captured and Silver is stuck in a standoff with two Spanish sailors while Flint is tied up.
Flint: (Nodding at one sailor) "Shoot this one."
Silver: (Indicating the other sailor) "He'll get to the pistol."
Flint: "This one has more scars... more fights. You've got a better chance against that one."
Silver: "Not if he shoots me first."
Flint: "Then beat him to it. Do it, quickly."
Silver: "So I actually have to fight him?"
Flint: "Well, what the fuck did you think was gonna happen?"
- Silver's attempts to get into the crew's good graces. It involves giving them daily updates on the goings on on the ship. Not only do his reports include important matters such as course heading and the ship's current location, it also contains gossip that Randall has observed and passed on to Silver. At first, Silver is punched to the floor before he can even get to his gossip because he's interrupting the crew while they eat. However, as the days go on, and he starts reading the gossip, though he doesn't name names, whoever he's talking about comes up and punches him as he reveals certain embarrassing details about their lives. The turning point, and the best one, comes on the fourth day:
Silver: "Next item... oh... A member of the third watch, who shall remain nameless, entered the pen late last night sometime after three bells. Though no one actually saw him enter or exit, evidence of his presence was clear, as upon inspection, the dairy goat's anus was irritated from overuse."
(A crew member walks up to him and punches him a couple of times)
Joshua: "You fucked the dairy goat?"
(The crew member shrugs, and then Joshua punches him)
- Given a great callback in a later episode, where Silver's giving his address on the deck of the ship instead of the mess. As he stomps his foot (something he did from the very beginning) the entire crew stomps with him. Doubles as a Crowning Moment of Heartwarming, showing that Silver has, indeed, made himself indispensable to the crew.
- Max telling Idelle how to seduce Featherstone so as to get him and his crew to join up with Jack:
Idelle: "I'm going to fuck the living shit out of him."
Max: "Mon Dieu, Idelle. If he chooses to join Captain Rackham's crew, that decision must be heartfelt. It cannot be cast into doubt the moment the pleasure fades. And for that, you cannot just fuck him. You must seduce him." (Beat) Yes, there is a difference. The breath in his ear. The arch in your back when he thinks he is making you finish. The look in your eyes when you finally breathe again that tells him you would do anything he asked in that moment. Anything at all without hesitation. The story you tell him that night about when you were a little girl, about the place you hid from your mother where the world was quiet. A story you've never told another soul. The look of confusion you show him when you wake up the next morning that tells him despite the thousand other men you've awoken beside, that he is unique. That he has seen you vulnerable. And that you cannot live without him."
Idelle: "I completely understand. Just so we're clear, I still fuck the shit out of him, yes?"
- During the voting between Flint and Hornigold, Billy has to explain why, exactly, Flint is down one vote. Not only is it a treat to listen to, it's implied that this sort of thing happens fairly regularly in Flint's crew.
- Billy Bones attempting to give a 'pep-talk' to the crew's riggers after a rope breaks. It fails miserably.
- With Jack and Charles holed up in the fort, and a price on Charles' head, a crowd of former pirates gathers outside the gate. One of them constantly calls for Jack to open up, talking as if they were friends. Jack eventually orders his men to open the gate, and just as the man outside greets him, Jack shoots him in the head and the gates close again. It's topped by this exchange:
Charles: "Did you recognize him?"
Jack: "Paul... something or the other."
- After explaining his battle plan, which involves leaving Jack in charge of his ship...
Teach: "Ever captained a ship this size before?"
Jack: "Oh, god no."
Teach (patiently): "Have you ever captained a ship this size before?"
Jack (catching on fast): "Sure."
- The introduction of "Mark Read" in the final episode. More specifically, Anne's reaction; she sizes "him" up with a single look, and can clearly barely hold back her laughter at Jack's failure to realise she's a girl.