These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Broken Base: Oh God. The Monkey Island fanbase is notorious for being split, particularly for fans of a bunch of silly pirate games. Some believe that the series began and ended with Ron Gilbert, and everything from Curse onwards is a monstrosity with stupid cartoony graphics, abandoning the "funny characters in a serious plot" feel. Then we have those who came in with Curse, and believe the first two games to be quaint, and that they suffer from a lack of Dominic Armato's voice acting and Bill Tiller's beautiful art direction. On top of this, there are those who think Curse and Tales are brilliant games, just as good as the first two, but that they are still not "true" sequels, because they don't explain the ending as it was meant to be. The release of Tales has made another group rather prevalent, who like the first three but detest any others purely due to not being 2D and having keyboard controls. And then, finally, we have a rather "obscure" little group who doesn't care about these details, but likes all of the Monkey Island titles. (The only thing that the fandom does seem to agree on is that Escape is the weakest, but even that isn't universal.)
Ear Worm: The main theme is an in-universe example: If you ask Edward Van Helgen for a pirate story, he'll tell you about a pirate crew who went insane because they couldn't get the theme out of their heads.
But you can't die in Telltale games, either... can you?
Guybrush's Hand in the Hole joke in Curse culminates in the line "You're going to have to cut off my hand!" In Tales someone does.
Game Breaker: Each of the first four games has a keyboard command that lets you win the game. You don't usually get the full credits if you use it, though.
Though since the fun in adventure games is found in solving the puzzles, and you miss the entirety of the plot, there's not much purpose unless you want to hear the typically kickass credits music again.
The whole point of this was making fun of Sierra gamers who thought Lucasarts games were too easy because you could always win.
The Voodoo Lady's 'unbreakable five game contract'. Monkey Island was licensed to Telltale just for Tales and the Special Editions, afterwards it reverted to Lucasarts, who are now owned by Disney, who are unlikely to ever make any more Monkey Island games. So it turns out that making the fifth game in time was a real stroke of luck.
Memetic Mutation: "I found the treasure of Mêlée Island and all I got was this stupid T-shirt."
"Look behind you, a three headed monkey" and "I'm selling these fine leather jackets" are also popular ones.
Most of Murray's dialogue.
Memetic Sex God: Reginald Van Winslow. Being the most sexually active character in a game series will do that. Being attracted to anyone regardless of gender or species helps too.
Moral Event Horizon: LeChuck actually has many to his name, apparently, but in Tales of Monkey Island murdering Guybrush after pretending to be on his side for four episodes is considered his most heinous and evil action.
For some, it was his sadistic delight in torturing Guybrush in the climax of the second game.
Villain Decay: LeChuck's threat level dwindled quite a bit thanks to getting repeatedly killed by Guybrush. Tales reverses it, completely.
Initially averted in that the first game plays him semi-seriously, but the second game makes him terrifying.
The Woobie: Poor Wally. Poor, easy to torture Wally.
Guybrush always goes through a hard time, for drama and comedy alike.