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  • Awesome Ego: Murray is the epitome of the trope Small Name, Big Ego, but the sheer hilarity of his boasting and his hamminess make his SO much fun that fans love him for it.
  • 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.
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    • LeChuck's theme is also pretty damn catchy.
  • Ensemble Dark Horse: Murray...the evil demonic skull! Muahahahahaha!
  • Even Better Sequel The game that wins most popularity polls is actually the 2nd or 3rd game.
  • First Installment Wins: 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.
  • "Funny Aneurysm" Moment: One line from Curse, rendered much less funny by the fourth chapter of Tales: "Funny, I didn't think you could die in Lucasarts adventure games."
    • Technically, this is a Telltale adventure game.
      • But you can't die in Telltale games, either... can 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 Black Comedy.
    • 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.
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    • 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.
  • Germans Love David Hasselhoff: 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).
  • Heartwarming: 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 hte 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.
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    • Minnie "Stroni" Goodsoup and Charles DeGoulash getting together again after years
  • Hilarious in Hindsight: At one point in LeChuck's Revenge, Guybrush asks LeChuck why he didn't just kill him when he came in, and LeChuck replies, "Because we had an extra disk." In Tales, 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 Harsher in Hindsight: The series started out being based on the original Disney Pirates of the Caribbean ride. Disney now owns 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 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.
    • The similarities between the plot of the first game and Pirates of the Caribbean: The Curse of the Black Pearl are actually fairly similar. Monkey Island fans noticed this pretty much straight away, especially noting a Cast of Expies. And then, Disney acquired Lucasfilm.
  • 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.
  • 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.
  • Only the Creator Does It Right: 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.
  • 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.
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