Mickey's Good Deed: Mickey hits rock bottom after his cello is trampled by a sleigh, and he ends up selling Pluto to a rich man's Spoiled Brat son just so he could afford something to eat (and perform the eponymous good deed by buying Christmas presents for a poor mother and her large litter of kittens). It turns to happy tears at the end of the short when Mickey, sitting alone by a campfire roasting a sausage, is unexpectedly reunited with Pluto, who not only escaped but managed to grab a roast chicken on the way out.
Elmer Elephant, when the other animals are taunting Elmer for his nose and send him sulking away crying. Anyone who was bullied as a kid would remember how much that kind of treatment hurt.
The entirety of second Silly Symphonies version of The Ugly Duckling (as if that story weren't depressing enough). From the moment the Ugly Duckling hatches and gets ostracized by the duck family, much of the story is a tease! He gets into a birds' nest, but the mother bird rejects him. He thinks he's met a friend, but it turns out to be a wooden decoy. The Ugly Duckling is left in a Heroic BSoD until a swan family comes in to adopt him. It doesn't help that the Ugly Duckling is in fact a very cute cygnet.
Puppy Love in which Mickey and Minnie get into a huge fight when she thinks Mickey put a bone in her box of chocolates (it was really Pluto and Fifi) and they nearly break up.
The ending toThe Barn Dance, where Mickey fails to get Minnie over Pete. To be fair, it’s more Downplayed, considering how Pete was actually somewhat more friendly in the short, and Mickey was no better than him, but it still doesn't migitate how sad the ending can be.
"The Moose Hunt". Mickey grieving after he thinks he shot Pluto (who is playing dead).
Similarly, "Squatter's Rights," has the ending scene where Mickey thinks Pluto was shot, when in truth the butt of the gun knocked him out and Chip and Dale poured ketchup on him. Mickey has no idea of any of this though and thinks his dog was just killed, proceeding to cradle Pluto's head while tears pour out his eyes.
The ending of "Donald's Happy Birthday". Donald, thinking the nephews bought a box of cigars for smoke, he forces them to smoke the entire box in an almost sadistic manner. When he finds out that the box was actually a birthday present for him, he feels so guiltyhe shrinks to the size of a bug.
The featurette "Goliath II", where Goliath is spanked and branded a traitor for trying to run away.
The end of "Goofy and Wilbur." Wilbur was eaten by a frog and then the frog was eaten by a stork. Goofy is horrified and starts crying, but then attempts to cheer himself up, reminding himself that Wilbur wouldn't want him to do nothing but mourn and that he can find other grasshoppers. Then he breaks down even harder, yelling "But they're not Wilbur!" Goofy's crying isn't played comically over-the-top either: it sounds like someone genuinely grieving for a pet they loved.
The ending of "Donald Duck and the Gorilla" is a strange mix between this, funny and heartwarming. After Ajax is affected by the tear gas and starts crying, Donald laughs at his misfortune until he too falls victim to the tear gas. The short then ends with both duck and gorilla crying together and consoling each other.
