How does Winnie the Pooh, the bear "of very little brain" still remember Christopher Robin, long after he has become an adult? Simple. At the end of The Many Adventures of Winnie the Pooh, Christopher Robin made Pooh promise he would never forget him. Pooh kept his promise.
Pooh and company being toys in the A. A. Milne stories and real animals (perceived as them anyway) in Disney, means the two can blend together as puppets easily in live-action.
Several of the people in Christopher Robin's life mirror his old friends in the Hundred-Acre Wood:
Among his co-workers, there's a perpetually gloomy old man whose constant pessimism calls to mind Eeyore; a Know-Nothing Know-It-All woman who claims knowledge and skills (such as lip-reading) that she doesn't possess as much as she thinks she does, like Rabbit and Owl; and a nervous young man who seems to be anxious about everything, like Piglet.
Alternatively, the young man is meant to be Rabbit, and the woman (due to her short stature, pink dress, the fact that Piglet is sometimes mistaken for a girl and the similarly nervous energy she shares with the man) is Piglet. The office also has a man with round glasses and a somewhat beaklike nose, a level-headed secretary and a cheerful young man who could represent Owl, Kanga and Tigger, respectively.
Christopher's tiresomely enthusiastic neighbour, who is constantly badgering him to play games, may be a slightly more annoying version of Tigger.
Evelyn and Madeleine can also be seen as reflections on Kanga and Roo, being a devoted and caring mother and an inquisitive child.
Giles Winslow could be said to be a dark mirror foil of Pooh himself; both are cheerfully devoted to doing as little as possible and possess very little brain, but while Pooh is kind, friendly and warm, Giles is cold, ruthless and selfish. He could also be however a representation of the Woosles, only leeching work of others instead of emotions.
Pooh is the only one of the Hundred Acre Wood residents not to fall into a sugar coma after binging on cake at Christopher's farewell party. Stands to reason, as Pooh's diet is almost entirely sugar (in the form of honey) anyway.
When Christopher Robin pretends to fight the Heffalump to convince his old friends that he is who he claims to be, what does he use as the Heffalump? His briefcase, the symbol of his work, and the real "Heffalump" of the story.
Giles being likened to a woozle is more appropriate than what Christopher Robin says about him. What was the first thing we learned about heffalumps and woozles in Blustery Day? They steal honey. And Giles is a woozle because he's a soul-sucking bastard that lives off people overworking themselves, thereby sucking the sweetness, the honey, out of their lives, ruining them in the process while he goes off to play golf at his leisure. No wonder Eeyore, of all people, gave him such a stink eye that Giles noticed. Even he would be disapproving of anyone acting like a woozle.
