* "Jack's Lament." One can really sympathize with Jack's boredom that's begun to turn into ''despair''
-->'''Sally:''' Jack... I know how you feel.
* Jack's moment of despair when Sally uses the fog juice to try and stop him. It's a small reminder of just how happy the prospect of having his own Christmas had made him.
--> '''Jack:''' (heartbroken) There go all of my hopes, my precious plans, my glorious dreams!
** Immediately followed by...
--> '''CryingLittleKid:''' There goes Christmas!
* "Sally's Song."
* 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.
* Jack's cry of "Merry Christmas to all, and to all a good night!" as he plummets down to earth in flames from being shot from the sky.
* 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 the policeman driving through town, announcing that Christmas is canceled this year.
* 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]].
-->''"What have I done?\\
What have I done?\\
How could I be so blind?\\
All is lost, where was I?\\
Spoiled all, spoiled all\\
Everything's gone all wrong"''
** The original poem has Jack breaking down in tears when he realizes what he's done.
* 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.