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Deep Dive Questions and What to Expect with Return To Monkey Island


By Ezekiel McAdams


September 15 2022


  The much anticipated installment of the Monkey Island franchise, Return To Monkey Island, drops in just a few short days on September 19.


Return To Monkey Island is developed from Terrible Toybox and published by Devolver Digital.

Returning to complete his story is original creator, Ron Gilbert. Joining him are several other recognizable, former LucasArts staff. Dave Grossman is co-designer and writer. Grossman was a part of TellTale Games which also created Tales of Monkey Island. David Fox joins as programmer. Fox had previously worked with Gilbert on the recent Thimbleweed Park.


Gilbert had previously left LucasArts in 1992 after completing the series sequel, Monkey Island 2: LeChuck’s Revenge to form Humongous Entertainment. After Gilbert left, LucasArts continued the series with two more installments. Curse of Monkey Island in 1997 with Larry Ahern and Jonathan Ackley as co-designers and Escape From Monkey Island in 2000, designed by Mike Stemmle notably from Sam & Max Hit The Road.


Gilbert had previously said on his blog Grumpy Gamer on April 13 2013 that if he ever got the rights back, he would entitle his version of Monkey Island 3, which he tentatively titled at the time Monkey Island 3A. While the original post has been deleted, his comment is down below.

Ron Gilbert Grumpy Gamer Monkey 3A post.png

  Now that raises an interesting question, will this installment continue with the canon previously introduced? Or will Gilbert and team disregard anything after Monkey Island 2? Or is there a third option, with the reveal of fan favourite character, Murray the talking demonic skull in the teaser, will they cherry pick from the prior iterations? Could we see the barber pirate trio of Haggis McMutton, Edward Van “Snugglecakes” Helgen and Cutthroat Bill? What about LeChuck’s new crew such as Dinghy Dog?


  Just to be on the safe side, let’s just stick to the first two installments Here are the characters that could return and the questions we have.


  Let’s do a DEEP DIVE on ALL THINGS Monkey Island. We will separate topics by the following categories; questions, characters, geography and worldbuilding as well as speculation and in-jokes.

Melee Island


  What happened to the stability of Melee Island when Governor Marley was kidnapped?

Is the Scumm Bar still open? Did Mancomb and Estevan return to a life of pirating?


Monkey Island


While the biggest question of the franchise has always been “WHAT IS THE SECRET OF MONKEY ISLAND?” will the history be revealed or developed? Who built the giant monkey head? Was it a portal to another dimension or underworld? Or was there always a labyrinth of catacombs beneath it?


Big Whoop


The plot of Monkey Island 2, is Guybrush looking for the treasure of Big Whoop. Like the secret of Monkey Island, what Big Whoop contains is never revealed, many clues are parsed through the game from the Voodoo Lady telling Guybrush that it is a portal to another world to others saying that that crew who hid it could have done so because of how terrible or beautiful it was. What is Big Whoop?


  One of the books you could check out from the Phatt City library was E Ticket. Was that a clue or just another reference to Disney Land and amusement parks in general?

  How did LeChuck find Guybrush under Dinky Island? Why was he waiting for him? If this was his plan all along to ambush and put him under a spell or curse, why was he concerned about Guybrush finding the map pieces to Big Whoop? He mentioned to Guybrush he intended to send him via the voodoo doll, to a dimension of infinite pain? Was this part of Big Whoop?    


  The cliffhanger ending of the sequel has long been up for debate over the last thirty one years. Did LeChuck put a spell on Guybrush? Were Guybrush and LeChuck always brothers and this was a child’s fantasy?

  There are clues sprinkled throughout the game that makes it out to be the former. From LeChuck’s glowing eyes in child form at the end to Elaine saying “I hope LeChuck didn’t put a spell on Guybrush” at the end.

Monkey Island 2 End 3 Original.png
Monkey Island 2 End 5 Original.png

Why did the Big Whoop Amusement Park look like the grounds of Booty Island?  Was it of any significance or a clue? Or just reusing art?

Monkey Island 2 End 4 Original.png
Booty Island Grounds Original.png

LeChuck’s Plans


  What were LeChuck’s overall plans other then revenge? Once he was reanimated he asked the voodoo priest for supplies to make a voodoo doll of Guybrush? He also wanted to make Guybrush’s remains and bones into a screaming chair. Did he intend both? Or was he just contrarian?

LeChuck’s Fortress


  Was LeChuck’s Fortress always his base of operations? If so, why was he anchored under Monkey Island in the catacombs? Or was it solely used for his purposes just the once? Why would the Voodoo Lady send voodoo supplies there? And why would LeChuck let her? Was she merely helping Guybrush? Or were they working together to achieve a mutual purpose?

LeChuck's Fortress Original.png
LeChuck's Ghost Ship Original.png

Governor Phatt


  Governor Phatt was the loathsome dictator of Phatt Island. Was there a connection between him and LeChuck? Phatt had intended to collect a bounty on Guybrush’s head, was there consequences for him when Guybrush escaped? What was his name? in the Phatt City library there were multiple titles written by him under L. Phatt. What does the L stand for?


Phatt Island

  Phatt Island is described as a fascist dictatorship by Captain Dread. Was it known by any other name prior to Governor Phatt? Who is the Gambling Society? Were they connected to Governor Phatt or separate? Who were the members other then the dealer, Raphie and Bruno the man behind the green door? When the dealer disappeared did he go into a tunnel under the island? Could it be similar tunnels like the ones used behind the waterfall?


Characters Fates

What became of Wally and Largo when LeChuck’s fortress exploded?


Guybrush’s Parents

We were introduced to Guybrush’s parents first through a dream sequence where they transformed to skeletons to help Guybrush navigate through LeChuck’s fortress later in the game. Who are they? In the tunnels at the end, we see their skeletons in the waiting room area, but was that a part of LeChuck’s spell or the magic of Big Whoop?

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Guybrush Parents Skeletons Original.png



  First off, as assumptions go, it’s safe to assume that some of the series regulars and beloved characters, Governor Elaine Marley, the ghost or zombie pirate LeChuck depending on his affliction, the island hopping Voodoo Lady, Stan and Herman Toothrot will return in some capacity.


  While not as relevant, could we see the Men of Low Moral Fiber as well? They appeared in the first two games.


  Could Wally B. Feed also appear?  Wally was central to the sequel and Guybrush’s quest to find Big Whoop.


  What about some of the lesser characters that weren’t as crucial to the plot but added to the world and ambience of the Monkey Island universe?


  When we were first introduced to wannabe pirate Guybrush Threepwood, it is Melee Island and its residents we first encounter.


Melee Island Residents


  What about the island lookout, the pirate leader and the Scumm Bar cook? 

Mancomb Seepgood,


Mancomb Seepgood Original.png


Esteven Original.png

Captain Smirk

  Captain Smirk was Guybrush's sword trainer and the audience's introduction to the sword fighting trial. One of the most enjoyable and fondly remembered is Guybrush testing out insults on the pirates of Melee Island. Is Captain Smirk still on Melee?

The Sea Monkey Crew


  Now let’s get to the crew of the Sea Monkey that Guybrush chose to rescue Elaine.

Depending on what path you took in Secret of Monkey Island, you either sank the ship leading to them being captured by the cannibals or they returned with Guybrush to Melee Island. Where is Carla the Swordmaster, Otis and Meathook? If Gilbert and team intended for them to be captured, will they be looking for Guybrush?


  Could we get a reunion between Carla and Captain Smirk of their adventures and history in Port Royal and as pirates?

Swordmaster Original.png
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LeChuck’s Crew



  Regarding LeChuck’s crew, will we see Bob return? Will we learn how Bob knew Carla, Ots, Meathook and Herman? Where was Bob in Monkey Island 2? Did he leave? He certainly didn’t seem to be happy to be coerced into being a member of LeChuck’s undead crew?

LeChuck Bob Ghost Ship Original Bob Origin.png
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Herman Toothrot and Bob Original.png

Largo LeGrande

  Where was Largo LeGrande during the events of the first game? He was mentioned by Bart and Fink in Monkey Island 2 that he was LeChuck’s right hand man, but was absent. Will this be explained? Largo told Guybrush they had been looking for a living piece of LeChuck to reanimate for years, are there other members of LeChuck’s crew we haven’t met? Will Largo return?   

Largo LaGrande Original.png
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Voodoo Priest

What about the Voodoo Priest that helped LeChuck prepare the voodoo doll for Guybrush? What is his role in the hierarchy if any?

Voodoo Priest LeChuck Original.png

Monkey Island Cannibals


  Were the Monkey Island cannibals natives or immigrants to the island? Were there more than three of them? What were the names of the other two besides Lemonhead? Could they have built the giant Monkey head or did they just worship it? Do they know the secret of Monkey Island? The cannibals mentioned the tourist trade. While most likely being an in-joke was there a time Monkey Island’s location was not secret? Will we see them return?

Monkey Island Canibals Original.png
Monkey Island Canibals Tourism Original.png

The Head of the Navigator


  What about the head of the navigator? Who was he? Captain Dread mentioned losing his navigator on an island, was that Monkey Island or a separate island? Will the navigator and Captain Dread be reunited?

Navigator Head Original.png
Captain Dread Navigator necklace 3.png
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Governor Phatt


 Governer Phatt could be an interesting character to further develop as he ran the island as a fascist dictatorship that proved to be a perfect haven for the Gambling Society. Will he return, whether related to LeChuck or not?

Governor L Phatt Original.png

Scabb Island Residents


  Regarding Scabb Island residents, what about Bart and Fink?

Bart and Fink Scabb Original.png

   Or Mad Marty, The Bloody Lip bartender, or the proprietor of the Swamp Rot Inn?

Captain Kate Capsize


Captain Kate Capsize of Chapsize Charters was tenacious, sarcastic addition. Her glass bottom boats were unique among the charter business. Did she discover that Guybrush framed her? Could we see her return?

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Kate Capsize Capsize Charters Boat Original.png

Captain Dread


  Captain Dread told Guybrush he could only sail between the three islands of Scabb, Booty and Phatt and not without his lucky sailing necklace? Could Captain Dredd return?

Captain Dread Original.png
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Big Whoop Crew


  What about the crew that discovered Big Whoop? The foursome consisted of Captain Marley, Rapp Scallion, the cook, Young Lindy the Cabin boy and Rum Rogers. Will they referenced or included in some way? Depending on what Big Whoop is, were they effected by it? If so, is that why did they split the map so nobody else could find it?




  Guybrush met a few animals in the first two games, could we get an appearance or reference to the seagull from Loom, a three headed monkey, Guybrush the dog or Jojo the monkey?


  Geographically, what is the distance between the islands of the first two games? Is Melee close to Booty, Scabb or Phatt? What about Monkey or Dinky? Where does LeChuck’s Fortress fit in?

  What has changed on Melee Island since LeChuck was defeated and the Governor left for Booty Island?


  The book on Scabb Island history from the Phatt Island library mentioned That Scabb was originally a quarantine island before becoming an antichrist haven for pirates without government, police or law or rules. Was there another reason why Largo chose Scabb to be his base of operations and enforce his embargo?


  Is the library on Phatt Island, one of the few in the Caribbean? Will Guybrush have the need to check out more books? The Voodoo Lady did say the fines were pretty steep.


  On Phatt Island, there was a network of tunnels behind the waterfall, what was the purpose and use of them? Why was a pump for the water needed to obscure the entrance to the tunnels? Did Rum Rogers construct them? Is there any significance or connection that that the tunnels under both Phatt and Dinky are similar? Most likely it is a reference to the tunnels under Walt Disney Land and World but is there more to it?


Booty Island is known as a party island, perpetually having Mardi Gras similar to Halloween Town in The Nightmare Before Christmas. Was it always a party island? Augustus DeWitt seemed to imply he never had enough time off to enjoy it?

  The treetop village above the Big Tree on Booty Island, who built it and what was the purpose?

Treetop Village Booty Island Original.png

On the map of Booty Island, there was a small neighbouring island or atoll on the right hand side. What was there, if anything?

Botty Island Map Original Attol.png

  When Guybrush first arrives on Dinky there is a tourist sign welcoming him to the island. Herman Toothrot had somehow found his way there to become a philosopher. Was its location hidden, or just not known as throughout the game there is confusion, which island is the location of Big Whoop? The Men of Low Moral Fiber mentioned they were stranded on an island, while searching for the treasure. Did they inadvertently stumble upon it? They mentioning meeting a philosopher? Did they meet Herman on Dinky Island?



            Finally just as a bit of fun, if Gilbert and team are pulling from the entire franchise, what characters and islands could we see return?


  Full disclosure, I haven’t played Escape From Monkey Island since it first debuted in 2000. It was never personally a favourite and I’ve never replayed or revisited it. I’ve also never played Tales Of Monkey Island and have remained purposely ignorant of plot, characters and world. I’ve heard nothing but wonderful things about the game.


Character Speculation

The Ferry Welshman


Could we see the Ferry Welshman? Who he is? Was he undead or a cursed traveler? Did he ever find his way out of the endless fog? Did he achieve a new occupation?

Ferryman Curse.png

King Andre

  How about King Andre and the Smugglers Cove on Blood Island? Could we see him return and the connection between him and LeChuck revealed?

King Andre Smuggler's Cove Curse.png

Dinghy Dog

  What a strange character this was. Where did he come from? Who was he? Was he a member of LeChuck's undead? Or just a carnival worker? Why did LeChuck defer to him? Was it just that he had no other right hand men he could count on such as Bob or Largo?

Dingy Dog Curse.png

Could we see more of the Goodsoup Hotel Empire dispersed between new and old islands?


Will Captain Rottingham plan his revenge?


While never established as a character the display of the giant snow monkey on LeChuck’s carnival ride? Do they exist in the Caribbean? Could we see a snowy or frozen island? Or were several snow monkeys haplessly marooned and became part of the fauna similar to the polar bears of the tv series LOST?

Snow Monkey Curse.png

Also mentioned was the legend of El Pollo Diablo, the Devil Chicken of Plunder Island, could we meet the beast?

El Pollo Diablo Demon Chicken Curse.png



  What about in-jokes? Throughout the first two games we have references and plugs for current and upcoming games?


  In the first game we saw Cobb plugging Loom in the Scumm bar with the seagull desperately trying to eat the red herring on the dock. There were references to both Indiana Jones and Sam & Max in both games, In the sequel there is a calendar of Buzzsaw Girl from LucasArts Nintendo game and animated Pilot, Defenders of Dynatron City.

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Defenders of Dynatron City Cover.png
Buzzsaw Girl.png


  In Curse of Monkey Island, there is a skeleton that looks like the skeletons from Grim Fandango in Captain Blondbeard’s chicken restaurant. The skeleton even had a button to inquire the player about the upcoming game.

  Will there any new references to possible upcoming games from Ron Gilbert? Or just delving into the history and archive of LucasArts? What about references to Zak McKracken,Paul Parkranger, Full Throttle, the Maniac Mansion series?                


  Will questions be answered? Will characters return? Will we build upon previous worldbuilding and mythology? Will we revisit islands such as Melee, Monkey, Scabb, Booty, Phatt and Dinky?

  What about new characters, new islands and locations?

  Are there any questions I missed that you have? Let us know in the comment section below.

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