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  • Aluminium Christmas Trees: Caber tossing is the real Scottish sport of heaving tree trunks. Unlike in the game, the objective is not to hurl it as far as one can, but about launching it so the tree rotates and reverses itself in the air and lands on its opposite end, with points awarded based on the achieved perpendicularity to the ground and landing direction.
  • Anticlimax Boss: While the third chapter is spent building up your ship's armory and your insult and comeback repertoire to take on Captain Rottingham, he actually proves a very easy opponent when you do face him. The fact that he always gets to say the insults actually works in your favor, since it means you don't have to worry about him potentially countering all three of your insults, and while he follows in Carla the Sword Master's footsteps by using his own insults, the fact that insults and comebacks in this game have to rhyme can help eliminate any extra difficulty that might have added. However, some rhymes end in a similar sound meaning it can be more difficult for a first time player.
  • Awesome Art: The game is without any doubt the best-looking adventure game that LucasArts ever released, with strong character animation, incredibly detailed backgrounds, and FMVs which feature animation that wouldn't have been out of place on a Saturday morning cartoon of the era. Many fans joke that the reason the game has never gotten an Updated Re-release was because, quite simply, it doesn't need one (beyond packaging it with ScummVM to make it easier to run on modern platforms).
  • Awesome Music:
  • Big-Lipped Alligator Moment: "A Pirate I was Meant to Be" appears out of nowhere and is forgotten in the next scene.
  • Contested Sequel:
    • A variation, since nearly everyone agrees it's a good game; the question is more how good. Some consider it the pinnacle of the series for its gorgeous visuals, strong dialogue and voice acting, and well-balanced difficulty curve (even in the Mega-Monkey mode). However, others consider it a minor step-back from LeChuck's Revenge, for abandoning that game's more open-ended format in favor of a return to the first game's "two island" structure, as well as the much Lighter and Softer overall tone.
    • Ron Gilbert, the creator of the first two games, did not work on this game, or either of its following sequels, Escape from Monkey Island or Tales of Monkey Island. At some point, he expressed a desire to obtain the rights to the franchise, at which point he'd instead make a new game that was a direct sequel from LeChuck's Revenge, calling it 3a. Come 2022, he eventually got to do this in the form of Return to Monkey Island.note 
  • Disappointing Last Level: Arguably the last two chapters, which have very little to do with the rest of the game's plot, forsaking the epic quest to cure Elaine and the intriguing history of Blood Island to give us an uninteresting LeChuck showdown. You end up walking through a half-arsed parody of Disneyland, bringing a distinct shift from the piratey atmosphere from before, and the adventure and mystery of Plunder and Blood. What's more, they're notably rushed, with a significant amount of time taken up by a long and pointless exposition scene dedicated to tying up the plots of the previous games rather than that of Curse itself. More importantly, the puzzles of these two final sections were just rehashes of ones you did earlier in the game (hangover recipe and the exploding rum cask, respectively). Though it should be noted that at least the last point was par the course for the series as the final puzzle in 1 and 2 was a rehash of a previous puzzle in that game (creating anti-ghost soda and building a voodoo doll).
  • Ensemble Dark Horse: Most of the time Murray has in the game doesn't serve a purpose and the player doesn't even need to talk to him, but fans found his baseless arrogance so utterly hilarious that he returned in the next two games. In fact, he started as an Ascended Extra; the developers included him in the demo just to provide some humor while the players tried to solve a couple of the puzzles. He was so well-received they decided to include him in the rest of the game.
  • Genius Bonus: "Barbery Coast" is a reference to the real-life term for the coasts of North Africa, Barbary/Berbery Coast. It was a hotbed for piracy during the period the game takes place.
  • Harsher in Hindsight: If Guybrush sings to Edward Van Helgen enough times with his horrible singing voice, Edward will comment that he has suffered a stroke. Eddie Van Halen the musician Edward was named after, would uncannily die of a stroke in 2020. Making the joke a rather morbid prediction.
  • Hilarious in Hindsight: The Flying Welshman, played by Tom Kane, quotes Yoda in a very familiar voice ("you WILL be"), in the tradition of LucasArts's many ubiquitous Star Wars references. A few years later, Kane would begin voicing Yoda more and more in official Star Wars media, and is now at the point where he's racked up more credits as the character than even Frank Oz.
  • Lucky Translation: Palido Domingo's name works even better in the german version as Blassido Domingo.
  • Nausea Fuel:
    • Just about everything about the map to Blood Island. Since Palido has it tattooed on his back, Guybrush has to get it off by pouring cooking oil on Palido's back, causing him to burn and allowing Guybrush to peel it off. Even in-universe, it's treated as just plain nasty, as Guybrush remarks "I really wish I didn't have to do that," and later, Captain Rottingham is grossed out when forcing Guybrush to give it up at swordpoint.
    • Pretty much everything about the food at Blondebeard's is disgusting. The blackened Cajun chicken is inedible, the biscuits are full of maggots, and most of the chicken dishes seem to consist of things like beaks and wattles.
  • Nightmare Fuel:
    • The consequences of mixing the drinks in order to (almost) kill Guybrush were downright terrifying for kids playing back in the day.
    • Also, looking through the crack in the Goodsoup family crypt and popping up behind the stump in The Secret of Monkey Island's Mêlée Forest, while the original music plays was very disturbing.
    • Exiting and entering Stan's shop multiple times may lead to a cutscene showing a woman trapped in spider's web, being chased by the spider who made it. They use 3D models unlike any other characters in the game and no words are spoken during it while Guybrush merely looks on, expressionless. Then you're uncerimoniously booted out of the crypt, never being given any explanation for the unsettling scene. It's a reference to The Dig, not that that makes it better...
    • The super-secret Easter Egg where you end up under Secret-style Mêlée Dock, the same music plays, and Guybrush casually comments on his own dead corpse is the worst.
    • LeChuck's resurrection on the pirate ship, and the pirate screaming at the sight before LeChuck kills him and turns him into a skeleton.
    • Everyone who rides LeChuck's rollercoaster dies screaming as the rollercoaster dips into a river of lava. They are still screaming as they emerge from the lava as skeletons to be conscripted into LeChuck's undead army. Just how many unlucky sailors lost their lives to that rollercoaster before Guybrush shut it down?
  • Retroactive Recognition: Mr. Fossey is voiced by Quinton Flynn just four years before he voiced Raiden.
  • The Woobie: Wally is the personification of this trope. The developers actually took out a scene from the ending of the second game where he is stranded on a raft, his monocle falls in the water, and he then falls in trying to retrieve it because they felt bad for him.
  • They Changed It, Now It Sucks!: When the game was released, fans of the first two games absolutely hated Guybrush's new lanky and tall appearance, as his original sprite art made him look short and stocky. It wasn't considered as good as the other two games, but since attained a classic status unlike the next sequel.

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