* The part where Alan Parrish comes back out of the board game after being in an alternate jungle dimension for 26 years, and goes looking for his parents, only to discover they're dead '''''and''''' that his father, who he thought never loved him, gave up everything he had to try to find him.
** Especially since he's really so childlike in that scene. "Where's my mom and dad?" ''(sob)''
** Not to mention that one of his first reactions after seeing Judy and Peter for the first time is to excitedly ask them if they're his younger brother and sister. ''Oh God...''
** Worse, when Alan returns to the abandoned shoe factory, he learns that his father [[DeathByDespair died of sorrow,]] and everything essentially was ''Alan's fault''.
** And without Parrish Shoes in business as the town's main source of income, why the town has become a veritable ghost town by 1995. Not only did Alan's disappearance affect his family, their business and Sarah, but it basically destroyed the entire town.
** Also on Alan's side, the careless accident where he left the sneaker on the conveyor belt in the factory, destroying his friend Carl's invention that would've unquestionably set him and the rest of the factory staff for life. Instead of taking responsibility for the mistake, he ducks out in a panic, leaving Carl to take the fall, all for ''Alan''. For this, he is fired and forced to make a living many years later as a police officer long after the factory shutters, constantly lamenting how he lost the opportunity of a lifetime.
-->'''Alan:''' Hey Carl...I know it doesn't mean much after 26 years...But I want you to know I'm sorry.
** On Alan's father's side, not only did he have to endure the AdultFear of losing his son and the PartingWordsRegret, but also he may have had to suffer the effects of [[WronglyAccused the stories that popped up]] [[NotProven about Alan's disappearance.]] Specifically, the one about him having killed Alan, chopping him up and spreading his remains around the house...
* Near the end of the film is another particularly heartrending moment; [[spoiler: Judy dying in her little brother's arms from a plant's poisonous barb. Her last words that she gasps out? "I...wish that mom and dad were here."]]
* Alan comes out with a really sad song that relays just how hard his life was: "In the jungle you must wait, until the dice read five or eight."
* [[spoiler: Alan and Sam's reconciliation]] is this mixed with a Heartwarming moment.
** Just these lines of dialogue:
--->[[spoiler:'''Sam]]:''' [[spoiler: I thought you weren't going to talk to me ever again.]]\\
[[spoiler:'''Alan]]:''' [[spoiler: Dad... whatever I said earlier... I didn't mean it.]]\\
[[spoiler:'''Sam]]:''' [[spoiler:''[looks a bit surprised, but hugs him back]'' Alan, I'm sorry too.]]
* All that Sarah went through after Alan was sucked into the game. She was made the town laughing stock after trying to tell everyone what happened, and was sent to therapist after therapist for most of her life, who tried to convince her that she was crazy.
-->'''Sarah:''' I was a little girl, Alan. You disappeared, and a bunch of bats surrounded me and chased me down the street. I was afraid. I'm sorry, Alan. No one believed me. I was all alone.
-->'''Alan:''' So was I. For 26 years, Sarah.
-->'''Sarah:''' Me too.
** Even the part after she wakes up from her faint and leaves a message for her therapist is this, for while it's slightly PlayedForLaughs, she still has tears in her eyes and her voice breaks a little as she tells the doctor she "needs her dosage checked", that she was sitting in the living room of the boy she saw vanish, drinking lemonade, and that she'd "really like to know what you make of all this." [[TheWoobie It's enough to make you want to give her a hug]].
* Alan scolding Peter for trying to cheat at the game and his MyGodWhatHaveIDone moment when he sees him cry.
-->'''Alan:''' Twenty-six years buried in the deepest, darkest jungle, and I still became my father.
* The ending, where Alan and Sarah meet Judy and Peter again (for the first time in the new timeline. It's implied shortly before that point that Alan and Sarah would forget a lot of their "old" adult life when they became teenagers again, but they not only remembered exactly what the kids looked like, they also sought them out to bring them and their parents to their town to be a part of their happy lives. Add in the panicked BigNo when their parents mention they're planning a ski trip to the Canadian Rockies (presumably the trip they died on in the original timeline), it shows how strong a love they have for the kids, and how great a debt they owe them. Their memories of the kids survived magic amnesia and the memory fade of 26 years.