* The very first character you meet in the game is Mêlée Island's lookout... who's half-blind. It [[EstablishingSeriesMoment instantly sets the tone]].
* The two sequences in which you try to steal the Idol of Many Hands. Much of the action takes place automatically in a room that you can't see; all you can see is dialogue and the actions that Guybrush is doing, many of which you can't normally do in the game. The highlight is perhaps "Hypnotize quarrelsome rhinoceros".
** This gem from the first of those two sequences:
--->''Push Red Button''\\
'''Sheriff:''' No! Not the red button!
* The "Ask Me About ''VideoGame/{{Loom}}''" bloke.
** What made the ''Loom'' guy even funnier was the fact that shortly after the Special Edition rerelease, ''Loom'' was rereleased on Steam as part of a Creator/LucasArts adventure pack.
* ''Secret Of Monkey Island'' has the option to let Guybrush greet [[TheBigGuy Meathook]] with the non-sequitur "I'm [[VideoGame/{{Loom}} Bobbin]] [[ShoutOut Threadbare]], are you my mother?" His response: "No, your mother was a duck."
* A crew who mutiny in the laziest way possible.
* While solving the catapult puzzle, the player might accidentally (or [[VideoGameCrueltyPotential deliberately]]) sink the Sea Monkey with a giant rock. This is Guybrush's reaction:
-->'''Guybrush:''' Whoops.
* The "rubber tree" remark, as both a subversion of and a TakeThat to TheManyDeathsOfYou in the Sierra adventure games.
* The cannibals with strange eating habits.
* One of the answers you can give give to the cannibals as a reason for them to not eat you is "Look! A three-headed monkey!", and it works for a second before they notice you are trying to run away and soon a three-headed monkey DOES appear behind them but they really won't fall for that twice.
* Repeatedly escaping from the vegetarian cannibals' hut causes them to increase security until the hut has a steel vault door, yet [[MyopicArchitecture the obvious escape route repeatedly goes unnoticed]].
* The revelation that Herman actually has a ''ship''.
* The realization that "The governor can take care of herself" is more than just an excuse not to go rescue her...
* The underwater idol puzzle, possibly the most hilarious example of CuttingTheKnot in all entertainment. Guybrush has been dumped off a pier, tied to a heavy golden idol. You have ten minutes to solve the puzzle before Guybrush drowns, one of the rare genuine deaths in a [=LucasArts=] adventure game. There are swords, scissors, knives, razors, shears and all manner of sharp cutting things ''just'' out of arm's reach. If you wait long enough, two guys walk onto the pier, [[HopeSpot lengthily debate]] tossing a sword into the ocean directly over your head...[[YankTheDogsChain then decide against it and walk off again]]. The solution, ladies and gentlemen: ''pick up the idol and walk out with it''.
* When Guybrush confronts [=LeChuck=], the two instantly drop into a childish spat of insult one-upsmanship that quickly ceases to make sense and can easily go into OverlyLongGag territory should the player allow it to.
-->'''[=LeChuck=]:''' You dare to come here and confront me? I can't believe your audacity!
-->'''Guybrush:''' Well, I can't believe your stupidity!
-->'''[=LeChuck=]:''' Yeah? Well, I can't believe your frivolity!
-->'''Guybrush:''' Well, I can't believe your enormity.
-->'''[=LeChuck=]:''' Yeah? Well, I can't believe your mobility.
-->'''Guybrush:''' Well, I can't believe your atrocity.
-->'''[=LeChuck=]:''' Yeah? Well, I can't believe your fragility.
-->'''Guybrush:''' Well, I can't believe your alacrity.
-->'''[=LeChuck=]:''' I grow tired of you!
-->'''Guybrush:''' ''''
* "[[AndYourRewardIsClothes I found the legendary lost treasure of Melee Island and all I got was this stupid t-shirt!]]"
* On Monkey Island, Guybrush finds the unfortunate impaled heads of three dead pirates, labelled Shish [=KeBob=], Shish [=KeJoe=], and Shish [=KeLarry=].
* Guybrush criticizing the pirate leaders.
-->'''Guybrush:''' You're a bunch of foul-smelling grog-swilling pigs!\\
''[Music stops]''\\
'''Pirate leader:''' To be a pirate, ye must also be a foul-smelling grog-swilling pig.\\
''[Music resumes]''
* Guybrush repeatedly picking on Meathook and calling him "cannonball-head" and then ramping up to "chrome-dome" after feigning an apology.
-->'''Meathook:''' Wanna see something ''really'' funny?
-->'''Guybrush:''' What, a picture of your whole bald family?
* While on Monkey Island itself, there is one scene where the sun is a selectable object. Instructing Guybrush to walk to it results in him turning to you and saying "Oh, sure. Walk to the sun". Even in the original non-voice version, the sarcasm is absolutely unmistakable.
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