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  • Aluminum Christmas Trees: If you examine Morgan's flyer in Chapter 1, Guybrush will reveal that he has a third nipple. Though this sounds like it could easily fit amongst all of Guybrush's other impossibly cartoony traits, third nipples are actually pretty common, especially with men.
  • Angst? What Angst?: Guybrush isn't particularly upset by the loss of his hand. Elaine gets over it pretty quickly herself.
  • Awesome Music:
  • Cargo Ship:
    • Before there was Winslow/Anemone, there was Winslow/The Map.
    • Apparently he and The Map are still platonic friends, as he keeps bringing it up even after he is paired with Anemone.
  • Epileptic Trees: Tales is like an incomplete puzzle that invites fans to submit missing pieces: especially regarding the role of the Voodoo Lady in setting the story in motion, and her allegiance and motivation. Also begging to be explained is Elaine's seeming prescience (made even more puzzling as she is not in her right mind most of the game) — people even theorize that Elaine has voodoo-like powers.
  • Faux Symbolism: According to Telltale Games' forum thread, there are PLENTY of examples of faux symbolism. They include:
    • In Chapter 3, Guybrush and his friends last a few days in the belly of a manatee, similar to when Jonah survived for three days in the belly of a whale.
    • Guybrush befriends Morgan and then gets betrayed by her and handed over to the Marquis De Singe on Flotsam Island for 30,000 pieces of silver... kind of like when Jesus befriended Judas Iscariot, who later betrayed him and handed him over to the chief priests for 30 pieces of silver.
    • In Chapter 4, Guybrush is brought to trial for charges, including that of spreading the Pox of LeChuck, and almost sentenced to death before LeChuck arrives to save him. In the Bible, Jesus was brought to trial before the Sanhedrin and before Pilate and Herod before being condemned to death with no one to help him, in order to fulfill the Biblical prophecy of long ago.
    • In the same chapter, Guybrush cures Elaine and everyone else across the Gulf of Melange of the Pox of LeChuck, and then gets betrayed by LeChuck and pierced by his Cutlass of Kaflu before dying; kind of like when Jesus was pierced by the nails of the cross and died to save humanity from all ills.
    • In Chapter 5, the map of the Crossroads is shaped like a cross where Christ was crucified. The map patterns are: Gateway = feet, Center = heart, Swordfight path = right hand, Treasure Hunt path = left hand, and Thieves' Den = head. Coincidence?
      • Arguable since it resembles more the veve/symbol of Papa Legba, who, like Galeb, is an important figure in Haitian Vodou who stood at the Crossroads and was responsible for allowing/denying communication between the land of the living and the afterlife, often portrayed as an old man with a walking staff, a pipe and an affinity for dogs, sound familiar? This makes it less of Christian symbolism and more a case of the people at Telltale Games actually doing the research.
    • In the same chapter, Guybrush makes his journey through the Crossroads, manages to unite himself in spirit with his body, and returns to destroy LeChuck once and for all through his trials and pains, before closing up the Crossroads with a sacrifice of his Shred of Life and using Elaine's ring as a part of the Crossroads exit spell to return to life and reunite with Elaine in the living world in his fully revived body. All of this makes a pattern to Jesus' descent into the netherworld and resurrection from the tomb to destroy death and Satan once and for all. Guess that's one more bit of faux symbolism added to this trope!
  • Ho Yay: Winslow's man-crush on Guybrush. The fans have exaggerated this.
  • Like You Would Really Do It: Even as cool as Chapter 4 is, did anyone really believe Guybrush would stay Killed Off for Real, especially with that zombie hand running around? Of course, the writers were probably smart enough to know this trope would occur, thus allowing the moment to have the "Holy Shit!" Quotient that it does. Yeah, everybody knew they wouldn't really do it, but show us somebody who actually thought they would try.
  • Moral Event Horizon: LeChuck trying to drown Guybrush, hanging him above a pit of acid, chasing him around with a voodoo doll, trapping him in a cursed theme park and stealing his wife was all in good fun. But LeChuck's running Guybrush through with his sword after pretending to be redeemed is something completely different.
  • Nightmare Fuel: Now has its own page.
  • Shipping: Some players think Guybrush should ditch Elaine for Morgan.
  • Shocking Moments: Chapter 4, to a greater degree than any other moment in the series. Not only is it revealed that LeChuck has been faking his Heel–Face Turn the entire game, but he finally crosses his Moral Event Horizon by murdering two major characters in cold blood. Both murders are played completely straight, contrasting the Death Is Cheap/Black Comedy way the series has treated death before, and bring the cartoony tone of the series to a screeching halt. Oh, and one more thing: one of those two characters is GUYBRUSH THREEPWOOD HIMSELF.
  • Special Effect Failure: In the scene in De Singe's lab in Chapter 2, De Singe and Morgan are quite blatantly standing in front of a flat image of the lab. Presumably this had to be done due to the filesize limit on the WiiWare release.
  • Squick: Guybrush gets creeped out wherever the Voodoo Lady's personal life is concerned. As the plot involves tracking down one of her ex-boyfriends, it happens quite a bit.
  • Surprisingly Improved Sequel: The general consensus is that the game, while not quite as good as the first three, is a significant improvement over Escape from Monkey Island.
  • Tear Jerker:
    • The ending of episode 4. Elaine and Guybrush's final exchange before he dies; obviously negated somewhat due to his resurrection at the end of the next episode.
    • Before that, there is also a scene in Chapter 4 when Guybrush is surprised to find Morgan LeFlay terribly wounded and holds her close as she tells him about the incident in the Marquis De Singe's laboratory, and after whispering out a warning to Guybrush (which he somehow misunderstands), she breathes her last; and he feels deeply grieved (though his Manly Tears may be invisible) as he pulls her sword from her not-bleeding body and has her hands enclose its hilt, tilts her head in a proper death pose and closes her eyes before getting up with an angry snarl of "De Singe!" The sad music doesn't help matters either.
    • In Chapter 5, you can examine the graves near the start for some funny Grave Humor... until you realise you just read the name of a character you met in an earlier chapter. Oh crap...
  • Villain Decay: LeChuck's ongoing decay throughout the series continues as he's brought back to life as a genuinely good guy. Then subverted when he drops the act and murders Guybrush.
  • Win Back the Crowd: After Escape from Monkey Island was widely criticized for its clunky transition into 3D, this game managed to prove that a Monkey Island game could be done with 3D graphics. Granted, it helped that graphics cards in 2009 were a lot more powerfulnote , allowing the game to have fully-3D environments instead of using the combination of pre-rendered and real-time 3D graphics that Escape did.
  • The Woobie:
    • While Guybrush has always been this to some extent, in this game it's taken up a notch.
    • Noogie. A nerd who's probably the nicest member of De Cava's crew. All he wanted was a date with Morgan LeFlay... When the rest of the crew, and their captain, pull a Face–Heel Turn at the end of their chapter, he's the only one who didn't approve... and an offhand (and missable) line implies they murdered him offscreen for it! A suspicion that would be proven true in Chapter 5.
    • Jerkass Woobie: Hemlock McGee's life keeps getting worse and worse. He only partly seems to deserve it.

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