* {{Adorkable}}: Guybrush is quintessentially adorkable. His first line ever includes an overly exuberant "I wanna be a pirate!", immediately exposing his adorkable lack of gruff and tough pirate attitude. In his first meeting with the beautiful pirate governor Elaine, he loses all power to speak coherently, uttering words like "blggw" and "dmnkly" (as the game was initially released in 1990, the jokes were in text).
* AwesomeEgo: Murray is the epitome of the trope SmallNameBigEgo, but the sheer hilarity of his boasting and his [[LargeHam hamminess]] make his SO much fun that fans love him for it.
* BrokenBase: Oh God. The ''Monkey Island'' fanbase is notorious for being split, particularly [[SeriousBusiness 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.)
* EnsembleDarkhorse: Murray...the ''evil demonic skull!'' '''[[EvilLaugh Muahahahahaha!]]'''
** And Reginald Van Winslow. He's so popular he got to appear in ''VideoGame/PokerNightAtTheInventory''.
* EvenBetterSequel: The game that wins most fan popularity polls is actually the 2nd or 3rd game.
* FirstInstallmentWins: Game reviewers always cite the first game as the best in the series. Fans on the other hand often like the second or third game best.
* GameBreaker: 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 [[SugarWiki/AwesomeMusic 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.
* GermansLoveDavidHasselhoff: For whatever reason, the series is popular in Germany.
** Is also very popular in Spain.
** Also in Italy, where some fan games were made and a fan book was written and sold (with its profits being donated to charity).
* HarsherInHindsight: One line from ''Curse'', rendered much less funny by the fourth chapter of ''Tales'': [[spoiler: "Funny, I didn't think you could die in Lucasarts adventure games."]]
** Technically, this is a Creator/{{Telltale|Games}} adventure game.
*** [[spoiler:But you can't die in Telltale games, either... [[VideoGame/JurassicParkTheGame can]] [[VideoGame/TheWalkingDead you]]?]]
** In the first game, Guybrush trains a monkey to hang onto the handle of the gate leading to the Giant Monkey Head. Three games later, we learn that the monkey never let go and eventually starved to death, leaving a family behind. Downplayed in that Guybrush's reaction to learning this is played for BlackComedy.
** Guybrush's HandInTheHole joke in ''Curse'' culminates in the line "You're going to have to cut off my hand!" In ''Tales'' someone ''does''.
* HeartwarmingInHindsight: Stan. Just... Stan. The guy is essentially the world's most inept con-man but he's always happy, no matter what he's trying to sell you, or how many times you screw him over. This includes trapping him in a coffin for several months, and then later committing insurance fraud to get rich and bankrupt him, both within the same game. Yet he's always happy to see you. He may just see you as another sucker, but in a world of piracy and evil voodoo magic, the fact that he is at least pretending to be nice is actually quite refreshing. Hell, he even THANKS YOU for trapping him in that coffin. because he feels you were the catalyst that gave him the idea for a new line of work by leaving him in there for so long.
** The Barbary Coast crew. When hiring them in ''The Curse of Monkey Island'', they refuse to go with you unless you can convince their two cohorts to go along too. Not only that, but they even have a song they like to sing together. Not only THAT, but when you arrive on Blood Island, Haggis [=McMutton=] reveals that they've talked it over and prefer a simple life of being pirate barbers, instead of pirates.
** Minnie "Stroni" Goodsoup and Charles [=DeGoulash=] getting together again after years
* HilariousInHindsight: At one point in ''[=LeChuck=]'s Revenge'', Guybrush asks [=LeChuck=] [[WhyDontYouJustShootHim why he didn't just kill him when he came in]], and [=LeChuck=] replies, [[MediumAwareness "Because we had an extra disk."]] In ''Tales'', [[spoiler:[=LeChuck=] actually ''does'' go right ahead and kill Guybrush without the formalities. This occurs at the end of the fourth chapter of a five-chapter series, each of which comes on a separate CD in the PC version... in other words, we ''did'' have an extra disk.]]
** Either this or HarsherInHindsight: The series started out being based on the original Creator/{{Disney}} ''Ride/PiratesOfTheCaribbean'' ride. Disney now owns Creator/{{Lucasfilm}}, and thus the rights to the ''Monkey Island'' franchise.
*** The Voodoo Lady's 'unbreakable five game contract'. ''Monkey Island'' was licensed to Telltale just for Tales, afterwards it reverted to Lucasarts, who are now owned by Disney, who eventually let Ron Gilbert and his company Terrible Toybox make another ''Monkey Island'' game along with Lucasarts (who had changed their name back to Lucasfilm Games).
** The similarities between the plot of the first game and ''Film/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl'' are actually fairly similar. ''Monkey Island'' fans noticed this pretty much straight away, especially noting a CastOfExpies. And then, Disney acquired Lucasfilm.
** The heroic duo of the series consists of an {{Adorkable}} blond and a FieryRedhead. [[WesternAnimation/KimPossible Sound familiar?]]
%% MemeticMutation:
%% "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.
* MoralEventHorizon: [=LeChuck=] actually has many to his name, apparently, but in ''Tales of Monkey Island'' [[spoiler: 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.
* OnlyTheCreatorDoesItRight: Zigzagged. The first two games are near universally agreed to be great games, which both involved the three fathers of the series. ''Curse'' is an inversion, as it is generally looked upon highly despite the fact that it had zero involvement from the creators, though it does have its detractors as well. ''Escape'' plays this straight however. ''Tales'' usually gets a pass since Ron Gilbert was involved with its production. If we're talking official series ''canon'' however, this is in full force, as people will typically only treat 1 and 2 as the ''real'' story. Doubly so since Ron has been on record saying that ''Curse'' was not where he had intended the series to go story-wise.
** And in 2022, Ron Gilbert (along with co-creator Dave Grossman) are returning to the franchise with the aptly titled ‘’Videogame/ReturnToMonkeyIsland’’.
* UnconventionalLearningExperience: The games with their dialogue-driven (but not too overly complicated) stories have helped non-English speakers learn how to speak English, if [[https://notalwaysright.com/ah-the-delightful-quirks-of-learning/293496/ this story]] from Website/NotAlwaysLearning is any indication.
* VillainDecay: [=LeChuck's=] threat level dwindled quite a bit thanks to getting repeatedly killed by Guybrush. [[spoiler: ''Tales'' reverses it, completely.]]
** Initially [[AvertedTrope averted]] in that the first game plays him semi-seriously, but the second game makes him [[NightmareFuel terrifying.]]
* TheWoobie: Poor Wally. Poor, easy to torture Wally.
** Guybrush always goes through a hard time, for drama and comedy alike.