The Style:
A whole lot of stuff that Jake posted up there looks like it could easily be from Curse of Monkey Island (the first!), from Day of the Tentacle, or – and that makes things interesting – from Return to Monkey Island. That one with the cobwebs from Mr. Magoo's Christmas Carol, a little color and texture adjustment and it could be a background down there in LeChuck's ship. Rex Crowle has stated that he's going for backgrounds that you'd finish in your mind, leave things open to interpretation. I guess 50's animators thought of it the same way, especially since 50's televisions were pretty skimpy on the detail.
But Rex also said that he'd love to see fan art that fills out all the blanks that he's intentionally left in there. Now that's something 50's animators could never hope for. In any case, I'm intrigued how this plays out (artistically, socially, culturally). My pencils and brushes are ready and version 1.0 of the locksmith is well messed up already.
The Secret:
I never thought of "The Secret of Monkey Island" as an untold twist in the lore that could be revealed and have the players gasp at how they could have overlooked that for more than 30 years. Guybrush found and experienced Monkey Island, above and below, so he's found its secret.
The Jokes:
I was a big fan of the anachronisms back then, because they were comparatively seldom. Fast forward four parts, and I got pretty annoyed at the prevalence of photographs and cameras in Tales of Monkey Island. 😘
The Meaning:
The first two Monkey Island parts were magical in that they actively encouraged interpretation. The sudden throwback to Melee Island in LeChuck's Revenge was a great example. This was a screen that in TSoMI had no other purpose than to get caught by Fester Shinetop in, basically a meaningless dark alley. It also had the circus poster – rather a poster of the prototypical circus that Guybrush still loved like a child, not the actual circus in which Italian madmen named after noodles fire him out of a cannon.
But like in literature, the author's art is not to bluntly hide "a secret" or "an interpretation" in a scene, but rather to combine core thematic elements until flashing associations give a spark to the imagination of the recipient. The first two MI games did that exceptionally well (there was a Melee Island throwback scene in CMI as well – an "easter egg" that didn't have an ounce of the same interpretative impact). I'd love to see similar things in ReMI again.