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1* AluminumChristmasTrees: 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, [[https://en.wikipedia.org/wiki/Supernumerary_nipple third nipples are actually pretty common, especially with men.]]
2* AngstWhatAngst: Guybrush isn't particularly upset by the loss of his hand. Elaine gets over it pretty quickly herself.
3* SugarWiki/AwesomeMusic:
4** The sweet [[https://www.youtube.com/watch?v=UhkfYFlovdU theme of Spinner Cay]], [[https://www.youtube.com/watch?v=iGGdBzCyAyo De Singe's theme]], [[https://www.youtube.com/watch?v=QHfeYVnifSE Morgan's swordfight theme]], [[https://www.youtube.com/watch?v=bylROu0zS5g Hardtack and Trenchfoot's theme]], [[https://www.youtube.com/watch?v=lOd8rxH06ks the Belly of the Manatee]], and the [[https://www.youtube.com/watch?v=f97zQ8ZnPZk finale]].
5** These songs can be part Creepy Music, part Awesome Music, and part Terrifying Music: "[[https://www.youtube.com/watch?v=-7xTSudSpNM De Singe's Battle Theme]]", "[[https://www.youtube.com/watch?v=FjeN6qPXi8I LeChuck's Revenge]]", "[[https://www.youtube.com/watch?v=Xqny3Qkxl1E Rise of the Pirate God]]", and "[[https://www.youtube.com/watch?v=ogrVU3Selng The Ultimate Battle]]".
6* CargoShip:
7** Before there was Winslow/[[spoiler:Anemone]], there was Winslow/[[spoiler:The Map]].
8** Apparently he and The Map are still platonic friends, as he keeps bringing it up even after he is paired with [[spoiler:Anemone]].
9* EpilepticTrees: ''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 [[spoiler: she is not in her right mind most of the game]]) -- people even theorize that Elaine has voodoo-like powers.
10* FauxSymbolism: According to [[https://www.telltalegames.com/community/discussion/18337 Telltale Games' forum thread]], there are PLENTY of examples of faux symbolism. They include:
11** In Chapter 3, Guybrush and his friends last a few days in the belly of a manatee, similar to when [[Literature/BookOfJonah Jonah survived for three days in the belly of a whale]].
12** [[spoiler: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.]]
13** In Chapter 4, [[spoiler: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.]]
14** In the same chapter, [[spoiler: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.]]
15** In Chapter 5, the map of the Crossroads is shaped like a cross where Christ was crucified. [[spoiler:The map patterns are: Gateway = feet, Center = heart, Swordfight path = right hand, Treasure Hunt path = left hand, and Thieves' Den = head. Coincidence?]]
16*** Arguable since it resembles more the veve/symbol of Papa Legba, [[spoiler: 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.
17** In the same chapter, [[spoiler: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!]]
18* HoYay: Winslow's man-crush on Guybrush. The fans have [[https://www.youtube.com/watch?v=Q7bVMHRPcgU exaggerated]] this.
19* LikeYouWouldReallyDoIt: [[spoiler:Even as cool as Chapter 4 is, did anyone really believe Guybrush would stay KilledOffForReal, especially with that zombie hand running around?]] Of course, the writers were probably smart enough to know this trope would occur, [[Administrivia/TropesAreTools thus allowing the moment to have the]] JustForFun/HolyShitQuotient [[Administrivia/TropesAreTools that it does]]. Yeah, everybody knew they wouldn't really do it, but show us somebody who actually thought they would ''try''.
20** Let's face it: there's no way anybody bought for a second that [[spoiler:[=LeChuck=] really had a change of heart]]. At least the resulting [[TheUntwist Untwist]] coincided with him pulling himself out of his VillainDecay in one [[MoralEventHorizon good, clean,]] [[spoiler:[[HeroKiller hero-killing]]]] [[MoralEventHorizon stroke]].
21* MoralEventHorizon: [[spoiler:[=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.]]
22* NightmareFuel: [[NightmareFuel/TalesOfMonkeyIsland Now has its own page.]]
23* {{Shipping}}: Some players think Guybrush should ditch Elaine for Morgan.
24* ShockingMoments: [[WhamEpisode Chapter 4]], to a greater degree than any other moment in the series. Not only is it revealed that [[spoiler:[=LeChuck=] has been faking his HeelFaceTurn the entire game]], but he finally crosses his MoralEventHorizon by [[spoiler: 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 [[MoodWhiplash screeching halt]]. Oh, and one more thing: one of those two characters is [[spoiler:'''[[KillTheCutie GUYBRUSH]]''' '''[[OurHeroIsDead THREEPWOOD]]''' '''[[ShooOutTheClowns HIMSELF]]'''.]]
25* SpecialEffectFailure: 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 UsefulNotes/WiiWare release.
26* {{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.
27* SurprisinglyImprovedSequel: The general consensus is that the game, while not quite as good as the first three, is a significant improvement over ''VideoGame/EscapeFromMonkeyIsland''.
28* TearJerker:
29** The ending of episode 4. [[spoiler: Elaine and Guybrush's final exchange before he dies; obviously negated somewhat due to his resurrection at the end of the next episode.]]
30** Before that, there is also a scene in Chapter 4 [[spoiler: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 [[DyingClue warning]] to Guybrush (which he somehow misunderstands), she breathes her last; and he feels deeply grieved (though his ManlyTears may be [[MenDontCry invisible]]) as he pulls her sword from her [[BloodlessCarnage 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 "[[MistakenForMurderer De Singe!]]"]] The sad music doesn't help matters either.
31** In Chapter 5, you can examine the graves near the start for some funny GraveHumor... [[spoiler: [[MoodWhiplash until you realise]] you just read the name of a character you met in an earlier chapter. [[FridgeHorror Oh crap...]]]]
32* VillainDecay: [=LeChuck=]'s ongoing decay throughout the series continues as he's brought back to life as a genuinely good guy. [[spoiler:Then subverted when he drops the act and murders Guybrush.]]
33* WinBackTheCrowd: After ''VideoGame/EscapeFromMonkeyIsland'' 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 powerful[[note]](on the order of ''one-and-a-half thousand times'' the computing power, in fact, comparing the top-end cards available at the time of this game's release to those available when ''Escape'' was released in 2000)[[/note]], allowing the game to have fully-3D environments instead of using the combination of pre-rendered and real-time 3D graphics that ''Escape'' did.
34* TheWoobie:
35** While Guybrush has always been this to some extent, in this game it's taken up a notch.
36** Noogie. A nerd who's probably the nicest member of De Cava's crew. All he wanted was a date with Morgan [=LeFlay=]... [[spoiler: When the rest of the crew, and their captain, pull a FaceHeelTurn 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.]]

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