Broken Base: A Day For Eeyore, especially due to being packaged as part of the original film. While it's considered the standard heartwarming Pooh fare standalone, some don't think it suits as a companion piece to Many Adventures due to how different the aesthetics are.
"Funny Aneurysm" Moment: Pooh sings "I'm short and fat and proud of that" while doing his exercises in The Honey Tree. Amusing while he sang it but not so much when his weight causes him to get stuck in Rabbit's hole.
Idiot Plot: The whole thing with Pooh getting stuck in Rabbit's hole would've been avoided if Pooh Bear just used the back door (which Rabbit shows that he has when rushing out to get help). Even when Christopher Robin actually suggests pushing Pooh back in (much easier than trying to get him out), where he could at least attempt using the to-all-appearances larger back door, Rabbit refuses to even try this, claiming "he's gotten this far".
Memetic Mutation: An image of Pooh reclining in Rabbit's house in the Tigger Too segment is a popular image on 4chan, with one image having the Scumbag Steve hat put on him.