* ActingForTwo: There are a lot of actors who voiced multiple characters (even though said characters have never met each other). They are: Alexandra Boyd, who does Elaine and the Son Pirate; Denny Delk, who does Murray, Skully and the Father Pirate; Michael Sorich, who does Edward Van Helgen and Charles [=DeGoulash=] the Ghost Groom; Terry [=McGovern=] as Captain Blondebeard and Cruff; Creator/TomKane as Captain René Rottingham and the Lost (Flying) Welshman; Harvey Jason as the Cabaña Boy and Effete [=LaFoot=]; S. Scott Bullock as Lemonhead and Pirate #2; Victor Raider-Wexler as Slappy Cromwell and the Snowcone Guy; Creator/DaveFennoy as King André and Pirate #3; George [=DelHoyo=] as Palido Domingo and Pirate #1; and Roger Behr as Mort the Gravedigger, Stu Boyle and Pirate #4. Even Dominic Armato can have a short "conversation" with himself (he also voiced the incomprehensible restaurant drive-thru speaker).
* ActorAllusion: Creator/AlanYoung voicing a character named [[WesternAnimation/TheRenAndStimpyShow Haggis]]. Only difference is here, his last name's [=McMutton=] and the former's [=MacHaggis=].
* FakeAmerican: The Son Pirate from the end credits. Alexandra Boyd performed an American accent perfectly.
* FakeNationality: Caucasian Kenny Falmouth is voiced by African American Gary Coleman.
* KeepCirculatingTheTapes: Until March 2018, this game and [[VideoGame/EscapeFromMonkeyIsland its followup]] were the only two ''Monkey Island'' games that still lacked a modern re-release on digital distribution platforms (as the first two games have remakes with the original versions as an EmbeddedPrecursor and the fifth is readily available on multiple platforms and storefronts). It is now released on Website/GOGDotCom and Platform/{{Steam}}.
* PromotedFanboy: Dominic Armato, voice of Guybrush Threepwood, was a long-time fan of the games. He may have won the role ''because'' he was a fan -- it was close between him and another actor and his love of the franchise was the tipping point.
* RefittedForSequel:
** The idea of Big Whoop being a portal to hell which transformed anyone who used it into an undead monster was actually something taken from Creator/RonGilbert's earliest pitch for [[VideoGame/TheSecretOfMonkeyIsland the first game]], then known as ''Mutiny on Monkey Island''.
** Similarly, unsuspecting pirates being lured to Monkey Island so that they could be forced into becoming part of the BigBad's undead army was also taken from ''Mutiny on Monkey Island'' -- albeit there the Big Bad wasn't [=LeChuck=], but a prototype version of Governor Phatt.
* TechnologyMarchesOn: The Destructomatic T-47 armor-piercing carnage delivery System with auto-loading and fax-modem is now doubly anachronistic - fax modems didn't exist in the 17th century, and aren't considered cutting-edge in the 21st.
* WhatCouldHaveBeen:
** Elaine was originally going to [[https://scummbar.com/resources/articles/index.php?newssniffer=readarticle&article=1013&page=1 turn into a wooden figurehead]].
** [[https://tcrf.net/Prerelease:The_Curse_of_Monkey_Island The official strategy guide reveals]] a parody of an AwardBaitSong called "Plank of Love" was going play over the closing credits, but the project ran out of time before it could be recorded, and shows a storyboard of a scrapped cutscene in which Elaine saves Guybrush from [=LeChuck=]'s roller coaster ride.
** In the CMI Strategy Guide, [[WordOfGod Bill Tiller revealed]] that El Pollo Diablo was actually real. An abandoned storyline involved a labyrinth underneath Plunder Island, filled with traps and clucks of chickens demanding vengeance on the chicken-eating world. Guybrush would have been captured and tortured there, eventually swearing off white meat for the rest of his life, after which he would have been trained in the sacred Way of Chicken, becoming an elite warrior of the Pollo Knights of the Sith.
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