* 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 [[SelfDeprecatingHumour 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.
* ''Disney/TheManyAdventuresOfWinnieThePooh'' 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.''
* ''Franchise/WinnieThePooh 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 FramingDevice, ''said fictional medium itself was fictional.'' That wasn't just PaintingTheMedium, that was tearing it down, building up a new one, and refurbishing the whole building. -@/KimikoMuffin
** Also, the title is almost certainly a reference to the 19th century political slogan, "Tippecanoe and Tyler Too." That was a massive DoubleTake 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 [[CompanionCube B'loon]] as if it were a real character, leading to a BrickJoke 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: [[spoiler:Most viewers would assume that Owl was just making stuff up about what the Backson looked like, but since it's RealAfterAll, Owl probably saw the thing at a distance and assumed that it was bad.]]
** A minor one, but [[spoiler: 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.]]
* In TheNewAdventuresOfWinnieThePooh, 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 ([[FailureIsTheOnlyOption 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 [[spoiler: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 ''WesternAnimation/PoohsGrandAdventure'', 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 HeartwarmingInHindsight 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 [[TheGlomp 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.
* ''WesternAnimation/MyFriendsTiggerAndPooh'' 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 AbsenteeActor in ''The Honey Tree''.
* The sign (which reads "Trespassers Will") above [[Franchise/WinniethePooh 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 [[spoiler: 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 TheNewAdventuresOfWinnieThePooh episode "Monkey See, Monkey Do Better", the group meets a giant wind-up gorilla GaryStu 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 commit'' '''''suicide!'''''
** Even worse when you consider that the initial choice actor for Bruno was Creator/RobinWilliams, 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 LivingToys, it's entirely possible that Roo has no biological father ''at all''.
* Rabbits are the most ''stupidly fragile'' animals known to veterinary medicine (the [[IncrediblyLamePun 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 BadFuture where his ControlFreak 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 [[SanitySlippage every other element of his mind has withered and been forgotten]].