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  • All-Star Cast: Besides the actors doing a Role Reprise the game has some pretty big voice actors filling many roles.
  • Auteur License: When Gilbert started the game, his biggest fear was Disney wouldn't let him make the game he wanted to make, but he remarked in his blog that they have been wonderful to work with.
  • Meaningful Release Date: September 19 is International Talk Like a Pirate Day, appropriate for a pirate adventure game.
  • The Original Darrin: Leilani Jones Wilmore returns to the role of the Voodoo Lady, who had been voiced by Alison Ewing in Tales.
  • The Other Darrin:
    • Earl Boen declined to reprise his role as LeChuck due to having retired from voice acting in 2017, while Kevin Blackton, LeChuck's voice actor for most of Tales of Monkey Island, had passed away that same year. As a result, the role is instead performed by Jess Harnell.
    • Cobb is voiced by Matthew Mercer, rather than David W. Collins, who had voiced him in the Special Edition of Secret.
    • Otis had been voiced by S. Scott Bullock in Escape and the Special Edition of Secret, but is voiced here by Sean Reyes.
  • Role Reprise:
    • Dominic Armato is voicing Guybrush once again, for the sixth time since 1997 in Curse.
    • Alexandra Boyd is back as Elaine Marley.
    • Denny Delk is once again voicing Murray.
    • Rob Paulsen returns as the voice of the Mêlée Island Lookout and Bob, after having previously voiced them in the Special Edition of Secret in 2009.
    • Neil Ross is back as Wally, having provided the voice for him since Curse.
    • Gavin Hammon returns to voice Stan S. Stanman after previously voicing him in Tales of Monkey Island.
  • Saved from Development Hell: Ron Gilbert wanted to create a sequel to 1991's Revenge for decades, but the transfer of the IP from LucasFilm to Disney seemed like the final nail in the coffin, and nobody expected a continuation of the saga at all, let alone made by the original creators.
  • Sequel Gap: Released in 2022. 13 years after Tales of Monkey Island. The game narrative picks up where Monkey Island 2: LeChuck’s Revenge left off in 1991.
  • Trolling Creator:
    • Announced by Gilbert on April Fools' Day, 2022. Gilbert had previously stated back in 2013, that if he ever made another Monkey Island game he would announce it on an April 1, and he decided to make good on this promise.
    • Gilbert heavily implied that the game would finally clarify the infamous Gainax Ending of LeChuck's Revenge, and the game does begin by appearing to pick up where that one left off... before revealing that it's actually just Guybrush's son and his friend re-enacting the game's ending and its immediate aftermath.
  • What Could Have Been:
    • Gilbert describes his original idea for "Monkey 3a" in the early 90s as "Guybrush chases the demon pirate LeChuck to hell and Stan is there.". This would be somewhat done later in the sequels, so Gilbert discarded it as a rehash.
    • Other ideas included: "Guybrush wakes up 3000 years in the future on a snowball Earth."
    • An extra island for chapter 4, Cogg Island, was cut due to a lack of dev time, which explains why one of the Golden Keys is a lot easier to get than the others. As an Easter Egg, you can still access a prototype version of it by using coordinates found on one of the trivia cards.
    • Earl Boen was approached to reprise his role as LeChuck, but declined due to having retired from voice acting. LeChuck is instead voiced by Jess Harnell in the final game.
  • Why Fandom Can't Have Nice Things: After the first full trailer was released, many fans who did not like the new art style went to Gilbert's personal blog to leave comments personally attacking him for the change, leading him to disable all comments on his blog and announce that he will no longer share anything about the game itself, writing, "The joy of sharing has been driven from me."

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