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1[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ab3edd79_7cc8_451a_8625_83e2088306cc.png]]
2[[caption-width-right:350:"What have I done?"]]
3* "Jack's Lament", wherein Jack laments how tired he is of being the Pumpkin King and wishes that he could give it all up. One can really sympathize with Jack's boredom that's begun to turn into ''despair''.
4-->'''Sally:''' Jack... I know how you feel.
5** What makes it worse is how "Jack's Lament" bounces from a [[IAmSong series of boasts and accomplishments]] to a [[MelancholyMusicalNumber somber realization]] of how ''tired'' he is of Halloween.
6** It's not just Jack's sense of ennui that makes the song hauntingly sad. It's the fact that nobody ''seems to understand'' what he's feeling (aside from Sally but they haven't had any scenes together yet). It's really disheartening to see Jack (who is essentially the Big Man on Campus of the town) talk about how his ennui and longing to do something different is something he can't really share with anyone.
7--->'''Jack''': Oh, there's an empty place in my bones that calls out for something unknown.\
8The fame and praise come year after year does nothing for...these ''empty tears''.
9* Jack's moment of despair when Sally uses the fog juice to try and ground him. It's a small reminder of just how happy the prospect of having his own Christmas had made him.
10-->'''Jack:''' There go all of my hopes. My precious plans, my glorious dreams!\
11'''Corpse Child:''' ''(crying)'' There goes Christmas!
12** What's more is that given how even Sally (after a brief "Phew!") eventually became more sad than relieved, she likely felt guilty about having to resort to such measures, but knew that she had no other real choice.
13* "Sally's Song." Even as she voices her concerns over her beliefs that Jack's plan will lead to disaster, she's also wrapped around the axle over [[IgnoredEnamoredUnderling her unrequited love for him.]]
14-->''"What will become of my dear friend?\
15Where will his actions lead us then?\
16Although I'd like to join the crowd\
17In their enthusiastic cloud\
18Try as I may, it doesn't last\
19And will we ever end up together?"''
20* While it's mostly played for laughs, one can't help but feel sorry for Jack being unable to reach the monsters at the town meeting. He's just experienced something new and exciting, something that's making him feel a sense of joy and happiness he hasn't felt in a very long time. Yet no matter how hard he tries to describe the joy of Christmas, the monsters can only respond back with the same Halloween sensibilities as they do all year, every year. In the end, Jack resorts to describing Santa in the most terrifying manner possible just to keep their attention, but as the curtain falls behind him backstage, he still wonders how he can get them to see Christmas the same way he did.
21* While it's played for dark laughs, it's rather heartbreaking to imagine being one of those children, who've presumably been good all year, who eagerly embrace their long-awaited presents only to be ''attacked'' by them immediately after.
22** Especially when you consider Santa's earlier line that there are "hardly any naughty kids this year." The one year he ''didn't'' have to punish anyone was the most traumatizing of all because some lunatic decided to hijack his holiday. No wonder Santa worked like clockwork to replace Jack's presents with safer ones.
23** The theory that the ''toys'' simply didn't know any better, and thought it was a game.
24** The very idea that some of these children may ''never'' get over what happened that year. Even though Santa still managed to fix things, suffice it to say, they can still possibly be quite scarred for life and never be able to enjoy Christmas ever again.
25** A minor one, but if you pay attention, the brother and sister who got the vampire duckie-on-wheels and the vampire doll ''eagerly'' played with them briefly before they attacked, meaning they still ''loved'' their toys even with the Halloween aesthetic. One wonders how many other children would have still enjoyed their Christmas if the Halloween toys were merely toys.
26* The National Guard blows Jack out of the sky. As he falls to his apparent demise, he still wishes a merry Christmas to all, and to all a good night.
27* The denizens of Halloweentown weeping at the supposed death of their beloved leader. The Wolf Man gives a HowlOfSorrow while tears run down his cheeks, and the Mayor tearfully drives through town announcing Jack's death on his car's loudspeaker. And then just to make it even sadder, it's intercut with all the kids in the Real World crying as the policeman drives through town and announces that Christmas is canceled this year.
28* The first verse of "Poor Jack." Until now, he thought he was doing the right thing, but he wasn't. Not at all. And he cries at [[MyGodWhatHaveIDone the realization that he's ruined Christmas]].
29-->''"What have I done?\
30What have I done?\
31How could I be so blind?\
32All is lost, where was I?\
33Spoiled all, spoiled all\
34Everything's gone all wrong"''
35** The original poem has Jack breaking down in tears when he realizes what he's done.
36** It's subtle, but that small whimper from Zero as he places Jack's broken jaw over him.
37* The Easter bunny's reaction to being transported into Halloweentown; one of the residents accidentally startled him, and the poor bunny leaps back into the bag, whimpering in terror.
38* When Sally gets captured by Oogie Boogie after attempting to free Santa to save Jack.
39* The audio epilogue has a happy tears version: Santa reveals that he's the narrator, and after what happened, he became friends with Jack. While visiting regularly, he sees that Jack and Sally have started a family. Santa at one point asks Jack if he would do that Christmas all over again, knowing what he knew. Jack smiles and says wistfully, "[[WorthIt Wouldn't you]]?"

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