When the others think that Eeyore is depressed from sitting on his hilltop all the time, they each take turns to cheer him up.
This episode contains examples of the following tropes.
- Arson, Murder, and Jaywalking: Piglet tries to think of something fun to cheer up Eeyore, from swimming, to dancing, to running, to ice skating, to yo-yoing to hiding under the bed.
- Balloon Belly: Both Pooh and Eeyore have these after eating a bunch of apples.
- Big Eater: Even though he ate enough apples to gain a sizable Balloon Belly - and enough that made Eeyore feel sick - Pooh is still looking forward to the remaining meals of the day and decides to have another big breakfast to figure out why Eeyore left.
- Cheer Up Episode: Pooh and the gang try to cheer up Eeyore by doing fun stuff with them.
- Debut Queue: Roo and Owl make their first appearances in the series here.
- Mistaken for Brooding: The others believe that Eeyore is sad and gloomy, so they decide to cheer him up in their own ways. Unfortunately, their well-meaning deeds, from stuffing him with apples to causing him to fall from the sky, nearly kill him. It isn't until Piglet talks to him that he reveals that he actually spends time on his hilltop using his imagination to paint the sky.
- Never Say "Die": Hilariously averted. Eeyore thanks the gang for their attempts to cheer him up, even if they almost killed him several times over.
- Oh, Crap!: After eating too many apples, Eeyore registers a look of horror when Pooh reminds him that they still have lunch and dinner to go making him run off.
- Oh, No... Not Again!: Eeyore's reaction upon seeing Piglet approach was to put on a football helmet.
- This Is Gonna Suck: Eeyore has progressively drier reactions to the various perils he's put in.
- Title Drop: After Tigger suggests that they cheer up Eeyore, Roo agrees, and says, "He'll be donkey for a day!"
