Winnie the Pooh
Pooh is a "bear of very little brain" which at first would seem to preclude his being much of a Taoist philosopher; however, one of the principle tenets of Taoism P'u, otherwise known as the Uncarved Block, which suggests that things in their uncarved state are powerful in their own simplicity. Pooh is the epitome of the Uncarved Block. Pooh has no arrogance, hidden depths or emotional complexities. In short he has no qualities that take away his absolute simplicity. Pooh is the poster bear for the childlike, simple secret of Tao - life is supposed to be fun and spontaneous, and when it is lived in this way life tends to just turn out right. Piglet observes this tendency in Pooh. Pooh has no "side" to him and is never looking for an angle or a reason to be pessimistic. He simply does what he feels like doing at the time, and it usually turns out just the way it is meant to.
Owl
Owl is the opposite of Pooh. He loves to have knowledge for knowledge's sake and so that he appears wise to everyone else. He doesn't like to share this knowledge widely but likes to keep it within a very small circle. He is not concerned with enlightening others. However, his knowledge, which is the knowledge of the scholarly, can seem a bit removed from the rest of us because it is not learned from experiences, and in Taoism knowledge gained from experience is actually more meaningful.
Eeyore
Eeyore is a pessimistic sort of fellow and unlike Owl whose knowledge is for the sake of having knowledge, Eeyore's knowledge is used for the sake of complaining about something. Eeyore' outlook on life obviously prevents spontaneous enjoyment and therefore prevents all of the knowledge that can come from spontaneity and happiness.
Rabbit
Rabbit likes knowledge so that he can be clever. He likes to be thought clever and believes he is happy in his cleverness. However, cleverness and wisdom are different things and Rabbit's cleverness demonstrates that over time, cleverness can become just a series of observations and involves no real enlightenment or insight at all.
Tigger
According to Tigger, "Tiggers can do everything" and Tigger's character is a demonstration of the foolishness of continually trying to do what one cannot do. Wise people know their own limitations but foolish people do not and Tigger definitely falls into the latter category. This gets him into a lot of trouble. It even makes him eat many meals he doesn't like because he constantly claims that Tiggers love eating everything - and finds that they don't.
Piglet
Unlike Tigger, Piglet is well aware of his own limitations. This makes him seem to be breaker than expected. He is an example of listening to our inner self and the importance of getting to know ourselves very well. Piglet is very well-acquainted with his In er Self and so is actually extremely confident for such a small animal.
