- "Stuck On Christmas": Just after Donald destroys the house chasing the turkey, the whole family (except for HD&L) looks around sadly until Donald notices the Christmas tree is still standing up and with a small smile says "Well, at least we still have the tree!" only to have the tree fall on top of him. Cue Daisy rushing to comfort Donald who just crawled from underneath the tree, bruised all over. It's an especially poignant moment for the character since, rather than turning on his nephews as they expect, he just lies on the floor, depressed and heartbroken, for what it is perhaps the first time actually showing humility and guilt over screwing things up. Meanwhile his nephews finally read the Christmas Card from him and Daisy that they ignored the whole time, a surprisingly touching message about Christmas being about love and giving to those they care about. For all the times they and their uncle have been at war, this is the point they realise they took things too far.Huey: I don't know about you guys, but I don't want to do that ever again.
Dewey: Me, too.
Louie: Me, three.
- In "A Very Goofy Christmas", Max doubts the existence of Santa and Goofy attempts to dress as Santa to get his hopes up. Eventually, his disguise is exposed, leaving Max devastated and with his belief in Santa shattered. Goofy tries to prove Santa is real by staying up all night watching for him but he has no luck and suffers a Heroic BSoD. Feeling sorry for his dad, Max dresses as Santa to cheer up Goofy.
- In the "Gift of the Magi" segment:
- Pete takes Mickey's hard-earned cash he was saving to buy Minnie a chain for her watch. Later, Mickey trades his harmonica at the pawn shop for said chain after his rendition of "O Little Town of Bethlehem" (as performed by session musician Tommy Morgan) impresses the shopkeeper.
- Just before the heartwarming moment, the way that Mickey and Minnie's faces fall when the gifts that they were going to give each other is missing their key components (harmonica case for Mickey is missing the harmonica; the chain is missing the watch) is heartbreaking.
Tear Jerker / Mickey's Once Upon a Christmas