My theory upon Winnie the Pooh from when I was baked as fuck:
Christopher Robin is dead and the Hundred Acre Forest is his afterlife, in life Christopher didn't have any friends so in his afterlife his stuffed animals are his friends because that's what he could relate too. Further evidence is that we never get to see his parent "to my knowledge". This leads me to believe that he never knew his parents, perhaps they died and he was in a foster home? Then why isn't his foster parents in his afterlife? Maybe they where mean to him.
A bit more fun take on the whole thing then the usual "he's psychotic" theory =)
So, your thoughts? Does my theory hold any water?