Owl and Rabbit are the closest things you come to "intellectuals" in the books (though Eeyore thinks he qualifies as one too) and seem to be slightly more "grown up" than the others — and they're also by far the most ridiculed characters, both thinking they're on top of the game and have it all worked out, while in reality they haven't understood anything. Makes a bit more sense when you find out that these two were the only characters invented wholesale by Milne for the books — the other characters were based on Christopher Robin Milne's toy animals and were given their personalities by Christopher Robin. Of course they'd be more childlike.
It's also subtly alluded to in The House At Pooh Corner where Rabbit tells Owl that "you and I have brains, the others have fluff." It can be taken, and is probably meant, as ego stroking and praising their own level of intellect, but does gain an extra dimension when you realize that Owl and Rabbit were based on real animals instead of stuffed toys — and so they would have actual brains instead of fluff.
As I recall it, in the cartoons, Rabbit and Owl have genuine fur/feathers and no stitches, so I think Disney interpreted it that way as well.
There's a theory that Owl and Rabbit are self-deprecating portrayals of Milne and his wife, or at least how he thinks Christopher sees them: AA himself always shut in his study writing, and Mrs Milne bustling around and insisting everything has to be organised.
While the record is silent on what he thought of his mother, Christopher Robin Milne himself stated that his father was always writing, so the theory does "bear" consideration.
Why is Eeyore always so down and depressed? Part of it may have to do with the fact he's the only quadruped animal in a forest primarily filled with bipedal animals. He can't use his hands/front feet the way they can, so he's far more limited in what he can do in comparison to them.
At first, it just seems like a Non Sequitur in "Piglet Meets a Heffalump", when Piglet describes the "Heffalump" (actually Pooh with the jar on his head) as looking like "an enormous big nothing". However, it actually makes sense in that the jar was (obviously) obscuring Pooh's face, so it looks like his head had no features on it.
The Many Adventures of Winnie the Pooh ends with a conversation about doing nothing and staying friends forever. Now watch the beginning of Pooh's Grand Adventure: The Search for Christopher Robin. It's the same conversation, word for word, making the latter movie the direct sequel of the former. - Kintatsu
One teaser trailer did say that this took place where Many Adventures left off.
It also gets another callback at the very end of the movie, which also recreates the last sentences of the book and ends with:
And here we shall leave them. And here we shall find them again. For the boy and the bear will always be together in this remarkable place ... called the Hundred Acre Wood.
Winnie-the-Pooh And Tigger Too, which I'd seen probably a decade and a half ago. The narrator makes himself known to Tigger, and then helps him and Roo down from the tree. In other words: Tigger uses the fictional medium he's in to escape his predicament. Not only that, but since this was a movie, with the book merely as a Framing Device, said fictional medium itself was fictional. That wasn't just Painting the Medium, that was tearing it down, building up a new one, and refurbishing the whole building. -Kimiko Muffin
Also, the title is almost certainly a reference to the 19th century political slogan, "Tippecanoe and Tyler Too." That was a massive Double Take moment for me when I realized it. -fierystage
The first part of the ending credits have the stuffed animals in Christopher Robin's room "acting out" scenes from the movie. The observant viewer will notice that only Pooh, Piglet, Tigger, Eeyore, Kanga and Roo appear as stuffed animals in this section; Owl and Rabbit are for the most part absent, and when they do appear they're represented by porcelain/wooden figurines that look nothing like them. Might seem a little odd at first — but it's really a call-back to the original books and A. A. Milne. Unlike the others, Owl and Rabbit weren't originally stuffed toys.
Also at the end of the movie, Pooh and friends are seen interacting with the end credits as they scroll down. Rather funny at first, but then you realize that Pooh and friends interact with their book's sentences like this all the time, so of course, it's perfectly natural for them to interact with the credits!
Again in the 2011 film, everybody keeps treating B'loon as if it were a real character, leading to a Brick Joke towards the end. Of course, we're dealing with a bunch of stuffed animals and figurines. B'loon is no less real than any of them are.
More from the 2011 fim: Most viewers would assume that Owl was just making stuff up about what the Backson looked like, but since it's Real After All, Owl probably saw the thing at a distance and assumed that it was bad.
A minor one, but when Pooh had little to no honey on his stomach, and was depressed about it? That was not from the original books, but from Return to the Hundred Acre Wood. Specifically, "In Which Pooh Goes in Search of Honey". Very sneaky, Disney.
Also, the reason Owl didn't fly his friends out of the Backson pit— it's been established in the books that he can't fly people places because of the "necessary dorsal muscles".
Expanding on the first point: Owl knew the Backson was real because he read about it in a book, just as he claimed all along. But the viewer is led to believe that Owl, much like a young child, dreamt up the Backson on the spot and then succumbed to Believing Their Own Lies:
After describing the Backson, Owl gives a Suspiciously Specific Denial by saying, "I swear that all I tell you is not made up!" When asked what a Backson does, Owl spends several beats saying, "I'm thinking, I'm thinking, I'm thinking, I'm thinking and now I will tell you!", making it look like he needs a moment to make something up from whole cloth. When asked what else a Backson does, Owl deflects the question with "Why don't we hear some thoughts from you?" The viewer is thus convinced that the Backson is a figment of Owl's imagination.
But if you rewatch the scene in the knowledge that the Backson is real, you realize that Owl simply couldn't find the book where he read about it. He spends a few moments looking for it, but at Roo's suggestion he resorts to drawing it instead. When asked what a Backson does, he needs a moment to think, not because he's making it up, but because he's trying to recall what he read. When asked what else a Backson does, he deflects the question simply because he can't remember any more details, but as usual doesn't want to admit to not knowing something. (Note how he first flips through a few pages of a book, still trying to find information about the Backson.) Unless you assume that him searching for information was just for show which would require either malice or a very extreme case of Believing Their Own Lies Owl really did read about the Backson in one of his books.
In The New Adventures of Winnie the Pooh, a common antagonist is a flock of crows. Most of the time they are shown as goofy-looking crows with Frank Welker's voice. Cut to the episode A Very, Very Large Animal, where the crows are now larger, more menacing, and have Jim Cummings' voice. Now one may pass this off as them being two different flocks. But it is entirely possible that since this is a Piglet-centered episode, we are seeing them through his eyes, where they appear to be brutes, where as other characters see them as the goofballs they are shown as in the rest of the series.
Near the end of Pooh's Grand Adventure, Christopher Robin explains to Pooh why he went to school. One of the reasons he gave was to learn how words are spelled, then dejectedly adds "and...how they're not." Perhaps he took an innocent word and accidentally spelled it to form something the teacher found offensive.
Or maybe he learned that Pooh's favorite food is spelled "honey" and not "hunny", and they've been spelling it wrong all this time.
A bit of both Fridge Brilliance and Fridge Horror (but mostly the latter)-the reason why some of the characters act as they are is because they represent psychological illnesses: Pooh represents eating disorder, Piglet represents generalized anxiety disorder, Rabbit represents OCD, Eyeore represents major depression, Tigger represents ADHD, and Christopher Robin represents schizophrenia.
Christopher Robin acts like every single child to plays with toys by making up names and personalities for them. Schizophrenia is a humongous leap.
In the 2011 film, various characters suggest alternatives to Eeyore's lost tail. Every time someone comes up with a (short-lived) solution, the whole gang sings a very cheerful congratulatory song. By the time they start to sing the song for Kanga, she cuts it off immediately and suggests they celebrate with silence. This of course is because she's a mother of a young child, and probably is a bit worn down by dealing with such songs all the time.
In the 2011 film, it may seem a bit odd that a piece of rope would be laying around the Backson trap just as they gang would need it most. What would it be doing there in the first place? But then you remember, Piglet dug the hole in the first place with Pooh "supervising", and he would need it to get out when he was done. They just forgot to take it with them when they were finished setting the trap.
In Pooh's Grand Adventure, Kanga, Roo, Gopher, are notably absent. But considering the fact that 1). Roo is a young child and Kanga would not want him going on such a dangerous expedition, and 2). Pooh and the gang were not provided the opportunity to ask Kanga and Gopher for help due to Owl rushing them out the door, there was no time for the gang to go out of their way to seek aid from the others when they were in such a hurry to find Christopher Robin.
It's sort of a Heartwarming in Hindsight case but in an episode of the TV series, Tigger much prefers the idea of bouncing rather than kissing Kanga for a romantic play, exclaiming "You always bounce someone you love". Essentially his bouncing is a form of affectionate Glomp, hence why he insists on doing it to his friends, never understanding any discomfort it gives them and getting very upset when they tell him not to do it.
My Friends Tigger & Pooh came out around the same time that news reports were talking about renewed tension between Disney and the books' copyright holders. Introducing Darby as a replacement for Christopher Robin may have been Disney giving themselves a possible out if they lost the rights to the Hundred Acre Wood—keep Darby, and give her a new batch of animal friends to have adventures with.
The newer Pooh projects seem to cause a blotch in continuity, many of them depict Kanga and Roo being the last members of the group to move to the Hundred Acre Wood with Tigger witnessing it. But in the original film, Kanga and Roo appeared first in The Honey Tree, then in Blustery Day, Tigger introduced himself to Pooh.... then he introduces himself to Pooh again. And to Rabbit again in Tigger Too. And Pooh another time in The Tigger Movie. Also given no dialogue from Pooh in Blustery Day actually specifies he's never met Tigger before (in fact he seems weary around him already), it's possible that this is just one of many, many cases Tigger made a redundant fanfare for himself, with him merely being an Absentee Actor in The Honey Tree.
The sign (which reads "Trespassers Will") above Piglet's door. The sign appears to be broken off at the "Will" part, and according to Piglet, Trespassers Will is actually his grandfather. Do you want to know what the sign actually reads if it was shown as a whole? "Trespassers Will Be Shot!"
Could be Will Be Prosecuted, which is just a tad sad rather than horrifying.
Either way, it's entirely possible that the sign was actually there before Piglet's grandfather, and he really did call himself "Trespassers Will". Or his uncle did ("Trespassers after his uncle, and William after Trespassers.")
In The New Adventures of Winnie the Pooh episode "Monkey See, Monkey Do Better", the group meets a giant wind-up gorilla Gary Stu named Bruno. After he misunderstands Christopher Robin telling his friends he isn't keeping him (he had meant to say he was a gift for a friend), Bruno goes to be in the woods by himself...and then sadly declares he needs to "unwind" and pulls out his wind-up key. He gets better when the main cast finds him and puts the key back in, but we just saw a heartbroken toy commitsuicide!
Even worse when you consider that the initial choice actor for Bruno was Robin Williams, who committed suicide after developing signs of Parkinson's disease.
"But the most wonderful thing about Tiggers is....I'M THE ONLY ONE!"...left?
He could just be bragging or boosting his ego, he is kinda immature and hyperactive after all.
Maybe it's not his species as we are led to assume, but just his name and he's the only one with that name?
Where is Roo's father?
Since they are Living Toys, it's entirely possible that Roo has no biological father at all.
Rabbits are the most stupidly fragile animals known to veterinary medicine (the runner-up being the horse), a fact of which rabbit-hunters frequently take advantage; often, they don't have to actually hit a rabbit with a bullet, the sound of a gunshot will startle it sufficiently to give it a heart-attack. Having a stranger pounce on you is a very startling event. In short, Tigger's lucky Rabbit didn't die the first time they met.
Also adds to Fridge Brilliance, considering Rabbit's constant neuroses and desires for peace and tranquility in the Hundred Acre Wood. He'd like to live a little longer, thank you.
There's a good reason why Eeyore is depressed: he's the only one of the original set of characters that doesn't have hands, which inhibits his quality of life to a greater degree than the other characters. Many of his recurring problems (i.e. finding a tail, setting up appropriate housing) would be much more manageable if he had hands of his own to work with.
In Springtime For Roo, the narrator presents Rabbit with a Bad Future where his Control Freak antics have become so unbearable that the other animals have left and the Hundred Acre Wood is nothing but a barren dying woodland. But keep in mind the Hundred Acre Wood is meant to be an imaginary play world made by Christopher Robin. In other words, one of his imaginary friends has become such an overbearing part of his psyche that every other element of his mind has withered and been forgotten.
It could also mean that Christopher Robin has created a new imaginary play world to which the other animals have moved, and this woodland on the brink of its imminent demise is what happens to an imaginary play world when there is no longer anyone imagining it.
Who was the previous occupant of Kanga and Roo's house?