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Some pretty big spoilers for Monkey Island 2 lie ahead.

At the end of Monkey Island 2, LeChuck and Guybrush end up in a universe where they are small children at a funfare, and LeChuck is Guybrush's bullying older brother. If you wait until after the end credits, you will see Elaine Marley standing at the top of the hole Guybrush fell into and saying "I hope LeChuck hasn't put some terrible evil curse on Guybrush".

The game is pretty equivocal about whether or not the whole thing is meant to be a child's imagination run wild. For example, the lift up from the underground tunnels in MI2 shouldn't in any consistent geography lead to the back alley from Melee Island in Monkey 1, since Dinky Island is an entirely different island.

Possibly this can all be explained by the onset of Guybrush's hallucinations being gradual, but the explanation offered in Curse of Monkey Island is not entirely consistent.

Have any of the people involved with the creation of Monkey Island 2 indicated what the hell was going on here, at least in their minds?

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The whole thing was a snowglobe. During a dream sequence. Also Guybrush was indoctrinated. –  Prinny Brocka Apr 9 '12 at 15:05
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up vote 18 down vote accepted

No, not in any uncertain terms. Ron Gilbert could work in espionage as his secret-keeping skills are first rate. I'm sure you must realize that explaining the ending to Monkey Island 2 is a question with as many answers as people who have played the game to the end.

The "cannon" (at least as far as all subsequent Monkey Island games are concerned) ending of Monkey Island 2 explained in Monkey Island 3 states that

it was a hallucination.

but the designers of MI3 had no insight into the original intentions of the end of MI2 as Ron Gilbert was not a part of that project and his original intentions were not shared. Because of this, many players have picked at the inconsistencies in the MI3 explanation as you do and consider the explanation provided in MI3 not to be cannon to Ron Gilbert's original vision which he seems intent to never reveal.

Ron Gilbert never explained what the Secret of Monkey Island is either. From the many interviews and ambiguous answers, it is rather clear that Ron Gilbert likes his secrets and may have no intention of ever clearing up any of this conundrum. He mentioned that he considered giving it to his lawyer to be read upon his death, but that this may lead to his untimely demise by a crazed fan desperate to know the secret.

Is any of it real? Is it the fantasy of a boy in an amusement park? What is the secret of Monkey Island?

We may never know. The wikipedia article has some good references and insight, citing several interviews with Ron Gilbert. Apparently Ron Gilbert intended a trilogy so the ending of MI2 may not have been meant to have the finality it almost implies if you take Guybrush's experiences at the end literally.

One stronger theory linked from the wikipedia article suggests that

when LeChuck first curses Guybrush after he falls down the hole, he does transport him to a parallel universe of hell and Guybrush's understanding of the world is shattered.

but it could even be as simple as something like

when falling down the hole or upon the landing, Guybrush hit his head and everything after that was a concussion-induced hallucination.

Any explanation that dismisses Guybrush's experiences at the end as being a hallucination is likely not going to please fans and so that's probably why it's for the better that it stays a secret. The best part of the ending in my opinion is that it is somewhat open-ended and allows players' imaginations to run wild and question the reality within the Monkey Island fiction. It's sort of surreal to be considering the "reality" within a fiction.

Personally, I feel that the scene with Elaine after the end makes it pretty clear what's what, but that's just my personal opinion. Either way, the game is a masterpiece.

I'm not sure if Ron Gilbert was making a joke, but on his blog, it read, "When @grumpygamer gets 1,000,000 followers, I'll make another Monkey Island." If that's true and someone's motivated enough to find out the truth of the Monkey Island mysteries, then it would seem some advertising of his twitter feed would be in order. FYI, Twitter has about 360,000,000+ registered users, of whom about 140,000,000 or so are believed to be active so you don't even need 1% of all twitter users to follow him - easy, right?

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Awesome answer. I freakin' loved these games. –  EBongo Apr 15 '12 at 4:34
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The Twitter link no longer says that, but Ron Gilbert has said that he'd like to buy the rights to Monkey Island and details here that if he did make another game, it would take place 2 minutes after the ending of Monkey Island 2 and in a carnival, thus answering the questions about the ending. –  Thunderforge May 19 '13 at 23:52
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