* Turning up in a "traditional piratey town" only to see buildings such as Starbuccaneers and Planet Threepwood.
* The "Pirate School" on Knuttin Atoll.
** Bonus points to the school's no-nonsense teacher Miss Rivers, hilariously voiced by [[Film/PlanesTrainsAndAutomobiles Edie McClurg]].
* Ozzie Mandrill's incomprehensible Australian insults, to which Guybrush can only respond with utter confusion.
-->'''Guybrush:''' Uh...well...Digeridoo to you too!
* Admiral Casaba's [=McCarthyism=]-style paranoia about pirates.
* You can also talk to Murray... Or make him spin around on his pedestal, which annoys him. There's absolutely no productive reason to do this. It's just funny.
--> '''Murray:''' If you don't stop spinning me, I'm gonna put an ''eeeevil'' curse on you! ''(Guybrush spins Murray again)'' That's it! You're cursed! You are gonna have ''such'' a rash!
* You can optionally kill Guybrush's future self (twice) in the mists of time and his hilariously casual reaction.
-->'''Guybrush:''' Gee, they're right... gun owners ''are'' five times more likely to shoot themselves.
* The duck.
* "No! ''My'' grog!"
* This exchange from the first act:
-->'''Carla:''' Do you have any idea how difficult it is to escape from Monkey Island?\\
'''Guybrush:''' No, how difficult is it to... '''[[TitleDrop Escape from Monkey Island]]!'''\\
'''Carla:''' ...Well, it's... really difficult.
** And then later when you meet Meathook
--->'''Guybrush:''' So how did you guys '''[[TitleDrop Escape from Monkey Island]]?'''
--->'''Meathook:''' Same way you did I suppose.
--->'''Guybrush:''' With Herman's hidden ship?
--->'''Meathood:''' ...''Herman had a ship?!'' That jerk never told us!
* The Dainty Lady Figurehead. Voiced by Pamela Adlon
-->'''Dainty Lady Figurehead:''' What is this compulsion you have to dress me up, you pantalooned FREAK?
* Ask Stan if he's working for Ozzie, and he will vent gloriously.
-->'''Stan:''' ''(Angrily)'' Ozzie Mandrill? Let me tell you something about Ozzie Mandrill, kid. Ozzie Mandrill doesn't know squat about being a real entrepreneur! He doesn't know the thrill of haggling, the ecstasy of a hard-earned sale, the agony of a lost customer! All Ozzie wants are orderly lines of zombies, queuing up to purchase his pre-fabricated, pre-priced, pre-processed garbage! I ask you, kid, where's the fun in that, huh?! Where's the love?
-->'''Guybrush:''' He wouldn't hire you?
-->'''Stan:''' ''(Glumly)'' Not even an interview.
* When Guybrush rides the lava flume ride, he will sometimes sing a little song:
--> '''Guybrush''': The temperature's a-risin'\\
And my sweat is vaporizin'\\
And I cannot feel my legs below the knees any more!\\
Oh, the lava is hotter\\
Than a flame-broiled otter\\
And my shoes are slowly melting to the fiberglass floor!