Yes. When it comes to addressing a worldwide audience, it’s more the typical association, than the real thing. In Monkey Island reggae works really well, because the original games are a depiction of a fabled piracy era, mixed with many elements of modernity.
It’s an imaginery of the place, instead of the real place depicted with historical precision.
It´s a bit like the current trend of stereotyping 1980s movie scores. While a good deal of movies actually had your synth scores by Tangerine Dream, Vangelis, Brad Fidel, John Carpenter, Giorgio Moroder, Harold Faltermeyer etc really the majority of (especially genre movies) is still classically orchestral. But the synthesizers feel more distinctive to a modern audience to that particular era.
Yes, that’s an interesting matter. If we want to find a difference, I’d say that in the case of stereotypes such Nepal music in Zak and 1980s movie scores, there’s something that really existed and that is depicted as more important than it was (the use of synthesizers), or that belongs in the same period but in a near region (indian musical instruments in supposed nepali music).
In the case of Monkey Island soundtrack, it’s more than this, it’s a construction of a fabled setting with elements that go beyond the time and space to fit a modern, emotional and fabled idea of what is characteristic of that zone, no matter if it’s from a totally different period.
There might be a big difference between geographical/cultural errors and anochronisms. You can´t really feel anachronsisms (especially in cases when all involved are long dead) but geographical and cultural errors can be more tangible to those concerned.
But you know, I´m really used to not minding that stuff. I´m from germany but I can really enjoy the part in European Vacation where they are in germany even though it´s actually set in a part of austria that is much closer to italy than to germany.
This one will stick in my mind forever.
Please, pardon me if it’s not an adventure. But I think it’s remarkable anyway.
I purposely decided to avoid to put an mp3 of this on my car’s ipod… it pushes you to speed up.
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Yep. Last ninja still one of the best. Crazy what sound could be achieved in a c64.
Monkey Island Theme on Eight Floppy Drives:
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About pirates, the whole pirate culture that most people believe is accurate was actually created by scratch by Stevenson in “Treasure Island” and reinforced by movies and other works (including Disney’s “Pirates of the Caribbean” ride) that were inspired by Stevenson’s book.
As you said, reggae rhythms in Monkey Island soundtrack have been chosen because people now correlate this genre of music with the Caribbean area, but even if Monkey Island had “Fifteen Men on the Dead Man’s Chest” in the soundtrack, that would have been another choice unrelated to real history.
It´s been really long time since I´ve seen “Master & Commander” but I seem to remember there was a scene where they play music on board, I think the era might be just about right and it´s not a downright pirate movie so maybe that kind of music would be close to the real thing? If there is such a thing as serious music culture in the carribean in colonial times at all.
Probably scottish/irish sea shanties.
I’ll share with you a video of “Safe In Arms”, another song from the soundtrack of Gray Matter, performed live by Raleigh Holmes and the Scarlet Furies. 
A little bit of adventure game history and context: this song has been composed by Robert Holmes, Raleigh’s father and husband of adventure game sensation Jane Jensen. (I wonder whether @RonGilbert ever interacted with her)
Robert was the composer of the soundtrack of Gabriel Knight: Sins of the Fathers and its sequels.
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I have remembered a song that is really a work of genius.
I know it very well not because I played the adventure game it comes from but because I’ve always been a Monty Python fan and I have discovered it a long time ago searching for songs written by Eric Idle. Here it is:
Song title: That’s Death
Game: Discworld II
Author: Eric Idle
Click here to show the full lyrics
There’s a place you’re always welcome
That’s as nice as it can be
Everyone can get in
’Cause it’s absolutely free!
That’s death
No need to take a breath
Just lie around all day
With not a single bill to pay
Hooray!
That’s death
No more sicknesses or flu
If you’ve lived beyond your means
You can die beyond them to
Boo hoo!
Well the greatest and the finest
Have already died
Why not simply join them
On the other side?
That’s death
Say farewell to all your bills
Rip up all your wills
And pop your final pills
Amen!
That’s death
It’s a tete-a-tete with fate
If you’re not feeling great
Then it’s the best way to lose weight, mate
Nothing here to hurt you
No one’s here to nag
Come die with me
If your life’s a drag!
That’s death
The wealthy and well-bred
All of them are here
And they’re all completely dead
That’s death
No more headaches, no more pain
Of the millions who’ve died
No one came back to complain!
You can’t take it with you
You can’t keep what you’ve got
So why not just lie back
And simply rot?
Just simply rot
It’s so cool it’s hot
That’s death!
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Nice! Has a clear “Galaxy Song” vibe to it!
I’ve not seen this movie and I’m not an expert about which music was actually popular among pirates, but I know for sure that classic songs like “Fifteen Men…” have been definitely created by Stevenson.
Some real “sea shanties” can be found in this website:
Monkey Island theme (to be precise MI2 opening theme) by far! Michael Z. Land! I became deeply attached with MI music since the original came and I play them regularly in my car.
Indy of course but it would be unfair to count the theme as a game soundtrack.
Sierra’s Phantasmagoria had great theme too. My screen name comes from that song.
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Interestingly race games had real good music. I loved Super Cars 2 theme so much! Lotus Esprit Turbo Challange was great too.
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And how did I forget Cruise for a corpse. This opening theme is unforgettable to me:
Generally speaking Delphine adventures ranked #2 for me after LucasFilm(Arts) ones.
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Yeah, but speaking of Delphine games, the intro that I have watched countless times was the “Out of this world” (“Another World” in Europe) intro!
Maybe it’s a bit off topic, since it doesn’t have a remarkable soundtrack, but… it was a really thrilling intro, and deserved to be mentioned somehow 
I have greatly appreciated THE DIG soundtrack.
Not only what you hear during the intro, but every soundtrack in the game.
Michael Land touched my heart.
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I wouldn´t say that. I think the soundtrack helped the mood of the game greatly. I replayed the anniversary edition on steam latly which has a difficulty setting I refer to as “humanly possible”. Good example of a game I´d love if it was a movie(because I just love the style), but damn playing it was no fun at all!
Also a deeply atmospheric score!