* Stede Bonnet would've tried asking the Spanish for his sugar back, but his Spanish is - as he puts it - "[[GoodBadTranslation very evil]]."
** And then he asks Edward if he's going to try bring it back for him when he infiltrates the fort
-->'''Edward:''' What, in my Drawers?
* While disguised as Duncan Walpole, a bonus objective has Edward taking RefugeInAudacity by ''pickpocketing'' the three Templars huddled around a table discussing their plans, ''for no apparent reason''. Given that he's already been winging it up to this point[[note]]with generally noncommital answers or silence in conversations, and improvising his Hidden Blade killing moves[[/note]], that is hilariously pushing it. Moreover, due to the history of the "full synchronization" bonus objectives, this means that ''Edward Kenway actually did this''.
** You could also look at the fact that [[spoiler:Edward Kenway was inducted into the Templar Order ''first''[[note]]even if it was under the guise of the ''actual'' defector, Duncan Walpole, Edward isn't a former Assassin[[/note]]]] so for much of the beginning of the game you're ''once again'' playing [[spoiler:a Templar surnamed Kenway]]... or the fact that [[spoiler:the Templars are ''just'' as prone to self-deception-by-assumption as the player may have been to assume them to be Assassins]]!
* Other than [[spoiler:the attempted Assassin attackers in Havana]], Edward's first subsequent encounter with the Assassins has him [[spoiler:evading Assassin guards on his way to a temple to find James Kidd]]... whereupon he promptly mistakes the Assassin Order for "Monks" of a "daffy Religion".
** For some added laughs, turn on the subtitles during this chapter. [[spoiler:It turns out the Assassins knew Edward was there the whole time and are just humoring his attempts at stealth.]]
* When a certain character reveals their true identity, [[spoiler:she (James Kidd/Mary Read), threatens to castrate Kenway if he tells anyone. She has a ''very'' peculiar smile on her face as she moves out of the frame.]]
** Also, Edward's initial [[UnusuallyUninterestingSight lack of reaction to it]].
-->'''Edward''': [[DeadpanSnarker Your name's not really]] [[spoiler:James]], [[DeadpanSnarker is it?]]
* When [[spoiler:The British invade Nassau]], "Calico" Jack Rackham makes the understatement of the year as [[spoiler:soldiers land on the beaches and start marching]].
-->'''Jack Rackham''': Well, I'll be hanged... It seems [[spoiler:King George]] has grown tired of our shenanigans.
* During the Assassin mission "Upton's Sorrow" as Edward guides the [[DrowningMySorrows sorrowful and completely smashed]] Upton across town...
-->'''Upton''': The church! In the name of the father, the son, and the holy- ({{beat}}) Mate, the father the son, and the holy- what's the third one again?\\
'''Edward''': Let's just keep moving, yeah?\\
'''Upton''': [[ComicallyMissingThePoint The father, the son, and the let's keep it move]]- no, that's not it.\\
'''Edward''': What does it matter?
** Then he stops to [[RefugeInAudacity take a piss in the middle of the street,]] while Edward has to fend off the soldiers who come to investigate.
** Also, in the tavern, he says to Edward:
-->'''Upton''': You, you are my greatest friend(swings at him) comehereI'llkillyou!
* When Edward finds Rhona Dinsmore, who's hiding under fire by hostile forces:
-->'''Edward''': I've come to warn you: your life's in danger.\\
'''Rhona''': [[CasualDangerDialog Aren't you the crafty one?]] [[DeadpanSnarker Whatever gave it away?]]
* Poor Stede Bonnet gets the full Blackbeard treatment in one part of the game, to the point that the entire screen actually gets darker as Thatch snarls in his face with those burning wicks coming out from under his hat. Then:
-->'''Thatch:''' Give your Quarry something to fear, some hellish ''Thing'' from a fever'd Dream, and Men will drop to their Knees, ''pleading for their Lord before aught else!'' ''AAARRRRRGGH''!
-->'''Bonnet:''' [terrified as Thatch looms over him] Oh... o-oh God...
-->[{{beat}}]
-->'''Edward:''' [casually] Looks fine.
-->'''Thatch:''' [nonchalantly, walking away as the screen returns to normal] 'Course it does.
* There is an achievement for getting drunk off your ass and waking up in a haystack.
* The in-game Abstergo emails and promos and information on their products are hilarious for being constantly EntertaininglyWrong. There's also the fact that they reject Altair, Ezio and Connor's stories as being not propaganda friendly. One can imagine that in some Assassin afterlife, the three of them are all smug about being too badass for the Templars while Aveline would be pissed off at being made a TokenEnemyMinority for the public.
** What sells it is the really bad American pronunciation of the names by the Abstergo analyst. This leads to gems like "Alltare Iben Lahad", "Enzio Owdeetory", and "Ratonagayden/Ratonatankon".
*** Fun fact: The Abstergo analyst is voiced by none other than RogerCraigSmith, Ezio's voice actor.
* Thatch's excited and obviously mood-lightening announcement about his "retirement party" is oddly ''adorable'' for the guy who made it his business to be the scariest guy on sea. [[spoiler:He unfortunately dies a couple scenes later.]]
* Vane's robbing of Edward's oysters when [[spoiler:they're stranded]] while waggling a stick around. Made even better by Edward's annoyed reply that there is plenty of food if he just tried looking. The entire mission is the first time the franchise dropped its historical dimension and devolved into pure slapstick comedy, with Vane and Edward essentially acting like a pair of toddlers fighting for room in a sandbox.
* [[http://www.youtube.com/watch?v=9pQ_ZozZIio This]] GoodBadBug.
** [[http://www.youtube.com/watch?v=SB9tCcfvW0Y Edward's new fighting style.]]
** [[http://www.youtube.com/watch?v=u8C1iRd8OrU Another,]] in which the Jackdaw turns into the Titanic.
** There is a glitch that will occasionally manifest itself where Edward will get his teeth stuck in a SlasherSmile-like grin. You can see a version of it [[http://youtu.be/0roE9m0V_Eo?t=19s here.]]
* When [[spoiler:Rackham betrays Vane and Edward, he maroons them on a damaged ship. The conversation between the two is bound to get a few giggles.]]
--> '''Vane:''' I'll gut you, [[spoiler: Jack Rackham!]] I'll open you up, I'll tear out your organs, and string a bloody lute with 'em!\\
'''Edward:''' Stop your god damned howling, Vane! It's no bloody use!\\
'''Vane:''' Well, well, the fearsome Edward Kenway speaks! Pray tell us, captain, how to quit this predicament! And tell us what genius you have for sailing a boat with ''no sails and no rudder!''\\
'''Edward:''' '''''[[PunctuatedForEmphasis SHUT! YOUR! GOB!]]'''''
** Even better is that it's a wide shot, as in, the ship is in full view with [[ThisIsMySide Vane on one side of the ship, and Kenway on the other]]. Anyone sailing past would get a glorious front row seat to the two's [[HamToHamCombat shouting match.]]
** The name of the mission? [[Film/IngloriousBasterds Vainglorious Bastards.]]
* During the mission "Claiming What's Due":
-->'''Torres:''' What is your true name, rogue?
-->'''Edward:''' It's, ah...Captain Pissoff!
* After Edward, Benjamin Hornigold and company take a Spanish ship in "Prizes and Plunder":
-->'''Hornigold:''' Anyone speak English? ''InglÚs?''
-->'''Spanish soldier:''' A little bit...
-->'''Hornigold:''' Tell your friends we're stealing your goods. And we won't hurt nobody if everyone stays as still as a sandbar. You got that?
-->'''Spanish soldier:''' Please...to repeat?
-->'''Hornigold:''' Oh, for fuck's sake.
** To top it off he then gives Edwards a [[http://youtu.be/I5EavAkHjQs?t=4m00s look and a little shrug]] while Edward grins at him
* The first instance of Observatory in action that Edward and the player get to see is [[spoiler: [[AntiClimax Jack Rackham mistaken James Kidd for a man while she is chatting with Anne Bonny, threatening to cut him(?) down if he doesn't lay off.]] What sells it is Roberts' reaction:]]
--> '''[[spoiler: Roberts]]''' : (In deadpan tone) A curious Bunch.
** It becomes funnier when you learn THAT REALLY HAPPENED. In fact, it was the incident that revealed that "Mark Read" wasn't, as Mary ended up outing herself to keep from getting killed by Rackham.
* Somehow, this troper finds the "Press any button to rattle the [[spoiler: cage]]." funny. Even the UI lampshades this, replacing all your action commands with "Rattle".
* [[spoiler: Abstergo's final trailer]] is already pretty funny on account of being EntertaininglyWrong and StylisticSuck... but one phrase in particular stands out: ''"Nothing is sacred, and everyone is committed."'' It appears the Templars have been secretly jealous this entire time.
* Early in the game, Edward runs into an Englishman at a tavern, who he immediately proceeds to insult:
-->'''Drunken Sailor:''' Fancy meeting a Welshman deep in Dago country. I'm English meself. Biding my time 'til the next war calls me to service.
-->'''Edward:''' Lucky [[TheHouseOfHanover King George,]] having a piss-pot like you flying his flag!
* While Edward and Charles Vane are discussing tactics in "The Fireship", Rackham is sitting atop several barrels of gunpowder...[[TooDumbToLive smoking a pipe]].
-->'''Vane:''' (walks over and smacks Rackham around) Bloody hell. You'd raise a cloud here, ya lout? You're sitting on enough gunpowder to blow New Providence off its rocks!
** Rackham's reaction doesn't hurt:
--> ''"Rackham: Lay off me, mate! I'm well chafed!"''
** What sells it is Edward visibly rolling his eyes, wondering what did he do to hang out with an AxCrazy psycho and a drunk incompetent.
* During the mission "Diving For Medicines":
--> '''Hornigold:''' Remember, Thatch, keep your cannons corked!
--> '''Blackbeard:''' Piss off, Ben!
* It can be quite amusing when a taken-over Fort takes down enemy ships, especially pirate hunters.
* At Woodes Rogers' party, a noblewoman asks Rogers [[HappyMarriageCharade how his wife is doing.]] His response:
--> '''Rogers:''' [[InVinoVeritas I haven't the faintest idea, and I don't intend to inquire any further. We separated almost five years ago, and both our lives have been the better for it.]]
** Another during the same party is when he drunkenly announces that he has been fired as governor of the Bahamas recalled to England due to his muck-up of Nassau.
-->'''Rogers''': ...And yet, for all my successes, his majesty has seen fit to sack me! And call me back to England! God bless the fucker!

* When Edward first meets Anto in "The Maroon Assassin":
-->'''Anto:''' What do you want, Englishman?
-->'''Edward:''' Edward Kenway. I'm here to warn you of danger. [[InsistentTerminology And I'm Welsh.]]
-->'''Anto:''' Hmph. [[MistakenNationality You all look the same to me.]]
** Amusingly, [[spoiler: by the end of the game, Edward has become an English nobleman.]]
* In ''Freedom Cry'', Adewale, of all people, has one of these moments when he starts gleefully gushing about the scientific benefits of Godin's expedition. His enthusiasm makes him downright {{Adorkable}}. It's a pity that he gets brought down only a second later by a WhatTheHellHero moment.
* The sound effect that plays when you rescue a shipwrecked sailor is the same sound effect you get for getting money or loot.
* In the second Subject Zero file, Warren Vidic's DramaticEntrance [[http://youtu.be/6mhui-bOq5c?t=13m16s "Here I come to save the day!!!"]]