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Girls Need Role Models: Out of all the Hundred Acre Wood residents, Kanga has the most common sense. This is in great contrast to her original book counterpart who was just as stupid as the males.
She's also cast in something of a Team Mom role, mind.
Then there's also Rabbit's slowly going insane when he's lost in the woods and the noises about him are fueling his paranoia (fittingly this scene was in fact animated by Don Bluth during his early run at Disney). Sort of doubles as a Funny Moment if you weren't scared.
Let's not forget the whole idea of the Rabbit's plan. Rabbit is seen as mature and somewhat level-headed as opposed to most of the residents of 100 Acre Woods. Yet he has no problem leading Tigger to his possible death.
If you think thats is not going to scare you, take the ENDING! A lot of viewers were also freaked out by the Pooh doll winking at the end of both the film and the original shorts. Chalk it up to the surreality of it (some were left fearing that their own dolls would come to life), and the fact that it comes out of nowhere if you're not expecting it. The dramatic fanfares heard during the closings don't help, either.
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).
Jerkass: Rabbit in And Tigger Too. Tigger is annoying him by bouncing everyone and ruining his garden, so what does he do? Plots to use his friends in a plan to leave him for dead in the middle of the woods. And when the gang realizes that forbidding Tigger to bounce would make him horribly depressed, all his friends are all for letting him bounce again... except Rabbit. He needs to be pretty much forced into not being a total doucheweasle.
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.
Uncanny Valley: The aforementioned Pooh doll winking at the end, which doubles as Nightmare fuel.