What is the charm about Pooh? I've been thinking about it, and I think part of what's so likeable about most of the children's books I've read for this class is that they work on two levels--one for children, which focuses on wonder, whimsy, and notions of "play", and one for adults, which focuses on cleverness and secondary levels of meaning. The Pooh books, though, are written for a much younger audience than the rest of these books, and they really only work on a single level, but in some way I think that that single level--innocent and carefree as it is--speaks to something in us that we carry with us from childhood but mostly ignore as frivolous. Wind in the Willows, too, I think, speaks to a similar notion of Arcadia--that realm that is lacking in the problems that characterize our adult lives, and which we identify with our own idealized childhoods--but focuses too much on the adult, transcendentalist notions of what simplicity and innocence are. Studio executives once complained that the Pooh stories lacked conflict, but that's central to what makes them so appealing.
Furthermore, they're genuinely funny. My favorite character is Eeyore, whose crippling depression is much more overstated and sardonic in the book. This is when Tigger and Roo are stuck in a tree (a plot element I do, in fact, recall from my childhood videos):
"I thought," said Piglet earnestly, "that if Eeyore stood at the bottom of the tree, and if Pooh stood on Eeyore's back, and if I stood on Pooh's shoulders--"
"And if Eeyore's back snapped suddenly, then we could all laugh. Ha ha ! Amusing in a quiet way," said Eeyore, "but not really helpful."
Eeyore is a jackass, and that's funny. It's also funny that Owl, the supposed wise member of the bunch, can't really read or write (he spells his name WOL). It's funny that Pooh, using a balloon to float up to a honeybee hive, thinks that he can trick the bees by painting himself black--like a small black cloud--and furthermore enhances the deception by singing a little song "such as a cloud might sing." Will it work? Who knows? "You can never tell with bees." Much of the humor, I think, is rooted in a child's sense of insecurity when compared with adults--by making the characters quite literally idiots, the humor is accessible to children, who, let's be serious, aren't very smart.
The history of criticism on Pooh is marked by scores of semi-serious books that use Pooh as a blank template to deal with concepts that Pooh really has nothing to deal with--I'm thinking of the Tao of Pooh, specifically, but there are also tons of half-baked lit crit theories on Pooh that revolve around feminism (Why does Kanga have to take care of all the other characters, anyhow?) or Marxism (How fucked up is it that upper-class Owl moves into poor lower-class Piglet's house?) or whatever. In some way, those books prevent us from looking critical at Pooh, but I'm not sure that there's any secondary level to be found here. If this were a book for adults, that might be a problem, but Pooh ought to get a pass just for being charming and idyllic. If it speaks to us, it's because there is a part of us that doesn't have that sort of need gratified enough.
N.B.: This book, The World of Pooh, contains two books: Winnie-the-Pooh and The House at Pooh Corner.