Winnie-the-Pooh
Weird thing about the title character of the one most beloved figures in children’s literature: he is never referred to simply as “Winnie” but is very often referred to simply as “Pooh.” Yes, the narrator will call him by the full double-dash moniker, but his friends out there in the Hundred Acre Wood generally just know him as Pooh. (Even more strangely, he actually started out life in a poem with the name Edward Bear.) Pooh is innocence personified…as a bear. There is nothing in the world he loves and cherishes more than his friends. Well, except for honey. He is smallish, roundish, loyal, determined, naïve and, above all, silly. What many readers outside of England don't "get" is that all the characteristics herein inscribed to Pooh can be very entertaining to adults when they realize Milne is poking gentle fun at at a certain type of comfortable British society.
Christopher Robin
The only human character in the Hundred Acre Wood is a young boy whom all the others look up to as the ultimate in intelligence and authority. Christopher Robin is famously based on the author’s young son named, well, Christopher Robin. Many of the adventures in the forest are directed toward a misunderstanding of human purpose by the animal characters.
Piglet
Piglet is, as the name suggests, a pig. He is also Pooh’s best friend. He is also somewhat afflicted by a Napoleonic Complex. As the smallest and weakest of the lot in the Wood (except for Roo, but then despite his name, Piglet is as fully grown as Pooh or Tigger), Piglet is constantly having to deal with the emotional effects of being a runt. As a result, he often becomes the favorite character of readers also suffering the same situation. He is a great role model because this desire to prove himself often allows him to show that size really doesn’t matter all that much.
Eeyore
Eeyore is a clinically depressed donkey who early on loses his real tail and has it replaced with a fake one pinned to his backside. He is very protective and proud of this tail because unlike his real one, it sports a beautiful pink bow. Eeyore’s name is derived from the braying of a donkey, but he doesn’t really have a braying personality. Some might say that Eeyore is a Captain Bringdown pessimist, but another way to look at him is as the voice of caution against going into dangerous situations without thinking too much of the consequences.
Tigger
Like, for instance, Tigger. He’s bouncy, sprouncy and fun, but Tigger is if nothing else a sublime portrait of the ADD personality before it was given that name. Tigger is sheer uncontrolled activity and as a result of his hyperactive desire to have fun over everything else, he sometimes presents an active danger to his friends. But, like the rest of them, he is also loyal and warmhearted in the end. Some might suggest the Hundred Acre Wood would be a safer place if there was access to Ritalin and while that may be true, it would also be a less interesting place.
Rabbit
The above assertion can be proven by the situation in which Rabbit attempts to become a kind of Ritalin by “curing” Tigger of his aggressive bounciness. It fails, of course, just as most of Rabbit’s attempts to impose authority and control over the nature of his friends fail. Rabbit does not intend to do harm; he is simply the absolute opposite of Tigger. Unlike Eeyore who sometimes tries to raise pragmatic points with his pessimistic outlook, Rabbit’s pragmatism is often simply a cover for his desire to control the narrative of his friends. Not out of a sense of authoritarianism, but simply because it would make his life so much simpler and easier.
Kanga and Roo
Considering the fact that the Hundred Acre Wood is an imaginative reworking of the fantasy world of the real Christopher Robin Milne, it should probably not be surprising that it is primarily a male-dominated world. Nor should it come as a surprise that the central female character is a symbolic mother of them of all. Kanga is a kangaroo and Roo is her joey, but in a much greater sense, Kanga becomes mother to everyone, doling out good advice, sincerity and patience. However, Kanga is also revealed to have a very sharp sense of humor and is willing to play along in many of the games taking place in the Wood.
Owl
If Kanga is the mother to all, then Owl is the symbolic father. He is the elder figure in the Wood and he also represents another example of Milne’s satire. Owl’s maturity level is conflated with his intellectual level and so the rest of the gang look to him to solve problems when Christopher Robin is not around. The problem is that Owl’s intellect is not exactly all he leads them to believe it to be. In fact, Owl is a bit scatterbrained and often makes the situation worse.
