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- Turning up in a "traditional piratey town" only to see buildings such as Starbuccaneers and Planet Threepwood.
- The "Pirate School" on Knuttin Atoll.
- 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.
- You can optionally kill Guybrush's future self (twice) in the mists of time and his hilariously casual reaction.
- 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... Escape from Monkey Island™!
Carla: ...Well, it's... really difficult.
- The Dainty Lady Figurehead. Voiced by Pamela Adlon
Dainty Lady Figurehead: What is this compulsion you have to dress me up, you pantalooned FREAK?