History TearJerker / OverTheGardenWall

* Poor Mr. Endicott's greatest fear is that there ''is'' no ghost, [[AdultFear and he's just going completely senile]]. Even with the happy ending, his age and overall demeanor give the impression that dementia really ''is'' a possibility. This makes Beatrice's plan to rob him while Greg and Wirt pretend to be his nephews particularly cringe-worthy -- seniors with dementia and other mental problems that affect their memory are often targets for theft, especially from [[EtTuBrute relatives and caretakers]].

* After Greg realizes that there's no hope for his brother, he makes the incredibly selfless decision to give himself up to the Beast in his place. It's Greg's defining moment as a character and is incredibly heartbreaking.

* Wirt's semi-disregard for Greg for half the series might be cringe inducing for anyone who has a sibling.

* After Greg realizes that there's no hope for his brother, he makes the incredibly selfless decision to give himself up to The Beast in his place. It's Greg's defining moment as a character and is incredibly heartbreaking.

[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/over_the_garden_wall_tearjerker.png]]
[[caption-width-right:350:''"Grow, tiny seed. You are called to the trees."'']]

* The somber, Latin reprise of "Potatoes and Molasses" when Wirt finds Greg [[spoiler: in the middle of turning into an edelwood tree]] is followed by a single line from "Come, Wayward Souls."

[[caption-width-right:350:''"Grow, tiny seed. You are gone to the trees."'']]

-->''Grow, tiny seed. You are gone to the trees.''

* Greg falling prey to the Beast and nearly freezing to death, all while maintaining his enthusiasm despite audibly getting weaker, is ''extremely'' hard to watch. The somber reprise of Potatoes and Molasses that plays when Wirt finally comes across Greg does not help one bit either. And the fact that Greg requests Wirt return the rock he had stolen from a neighbor indicates that he has grown a sense of mortality and believes he won't be around anymore.]]

* The somber, Latin reprise of "Potatoes and Molasses" when Wirt finds Greg in the middle of turning into an edelwood tree]] is followed by a single line from "Come, Wayward Souls."

** It's also sad as we are also saying goodbye to the characters we have fallen in love with. It's a powerful ending to one of the greatest animated cartoons not of this generation, but of all time.

* Wirt's reaction to [[spoiler: Beatrice's betrayal, especially since it was coerced and she was about to go back on it anyway when he found out]]. He's driven so far into despair by this that [[spoiler: he becomes prey for the Beast, which causes Greg to make a DealWithTheDevil to save him]]. His reaction when he finds out about ''that'' is also heartbreaking.
* After Greg [[spoiler: realizes that there's no hope for his brother, he makes the incredibly selfless decision to give himself up to The Beast in his place. It's Greg's defining moment as a character and is incredibly heartbreaking.]]
* Wirt [[spoiler: frantically yelling and searching for Greg when he realizes that he's gone, leading to him falling through thin ice (although he's saved by the fish that had been fishing earlier in the chapter) and losing consciousness. The desperation in his voice as he's looking for Greg really shows Wirt's CharacterDevelopment and how much Wirt's grown to care about Greg's safety.]]
* The perspective we get on Wirt's insecurities is really funny and really sad. [[spoiler: Wirt's paranoia about Greg and his stepdad persecuting him and his increasingly panicked attempts to get back the tape without having to actually talk to his classmates are hilarious, but even if his anxieties are ridiculous they're real to him. The other teens obviously care about him and consider him a friend, but he thinks they don't even want him around.]]
** [[spoiler:"You'll be no good to your brother dead." "I was never any good to him alive, either."]]
* Greg [[spoiler: falling prey to the Beast and nearly freezing to death, all while maintaining his enthusiasm despite audibly getting weaker,]] is ''extremely'' hard to watch. The somber reprise of Potatoes and Molasses that plays [[spoiler: when Wirt finally comes across Greg]] does not help one bit either. And the fact that Greg requests [[spoiler: Wirt return the rock he had stolen from a neighbor indicates that he has grown a sense of mortality and believes he won't be around anymore.]]
** From the same scene, [[spoiler: Wirt finally breaking down and apologizing for treating Greg poorly and getting them lost. He even has to be the one to give Greg the will to keep going]].
* The somber, Latin reprise of "Potatoes and Molasses" when [[spoiler:Wirt finds Greg in the middle of turning into an edelwood tree]] is followed by a single line from "Come, Wayward Souls."

-->'''The Beast:''' You've been [[spoiler:grinding lost souls]] for ''years''.\\

* The Woodsman's whole situation, but ''especially'' [[spoiler: when he realizes that his daughter's soul was never in the lantern to begin with.]]
--> ''[[spoiler:"You'll never see your daughter again, woodsman! Are you '''really''' ready to go back to that empty house?"]]''
* [[spoiler: Wirt and Beatrice's goodbye, which isn't shown onscreen, but can be overheard as the previous scene fades to black.]]
* The ending, [[spoiler: which reveals that the Unknown may have been AllJustADream, although there's a touch of OrWasItADream as well]].

--> ''The loveliest, lies of all.''

--> ''How the gentle wind,
--> ''Beckons through the leaves,
--> As autumn colors fall.''

''Beckons through the leaves,
As autumn colors fall.''

--> '''How the gentle wind,
Beckons through the leaves,
As autumn colors fall.'''