The following is from Kostya Kennedy’s essay in LIFE’s new special issue on Winnie-the-Pooh, at 100, available at newsstands and online:

HAPPY CHILDREN ARE all alike, the sage might have counseled; each unhappy child is unhappy in his or her own way.  A preponderance of enduring children’s stories, those with the fiber to last, say, a century or more, are marked by an unhappiness of one kind or another: an absent parent, an evil stepmother, poverty, unfairness, persecution. Witches lurk, giants snarl, spells are cast, and people die. Childhood in Winnie-the-Pooh? That’s a world driven by daydreams and idle moments, by fine ideas, generosity, and pleasure in small things. What was Pooh up to one morning?  “Well, he was humming this hum to himself and walking along gaily, wondering what everybody else was doing, and what it felt like, being someone else. . . .”

Good feelings bloom throughout the Hundred Acre Wood, feelings of comfort and ease and the possibility of a happy surprise. Problems don’t turn out to be such serious problems after all. Potential crises never quite materialize. Nothing really seems that bad. When we first meet Pooh, Christopher Robin has him by one arm and is haphazardly dragging him down a flight of stairs, the stuffed bear’s head knocking—“bump, bump, bump”—on each step. Pooh proves unbothered. “It is, as far as he knows, the only way of coming downstairs. . . . ”  

When a small worry does arise for Pooh, it can usually be placated by a taste of condensed milk or a lick of honey. You’re able to take life as it comes when you’re bound to a core belief that things are going to turn out all right. Above all, in the pages of the Winnie-the-Pooh books, there’s an overriding sense—the threat of running into a Heffalump notwithstanding—of being protected and safe. Is there a child of any age, 2 to 102, who doesn’t want that?

*

My daughter Maya started at the local dance studio at an age when the classes served in essence as a form of one-hour babysitting. By the time she was 6, she took part in her third annual spring recital, on stage in the high school auditorium. As ever, the extended family turned out. “You know, the first couple of years, you weren’t much good at this.” Maya’s grandmother, my mom, was blunt in the post-show assessment. “But this year, you really looked great up there! What happened?”

Maya considered this for a moment. “The truth is,” she then said, “for a long time, when I was younger in dance class, I didn’t really understand what was going on. But this year, I suddenly did! Now I do!”

Such epiphanies are common in childhood, inevitable markers for the developing brain and the continuing apprehension of the wider world. Pooh and his friends are not 6 (until, finally they are), and the capers they embark upon, or get thrust into, manage to be at once purposeful and desultory. They have a mind to do something they’ve dreamt up or heard about, but they aren’t quite sure how to go about doing it. It’s a bit like following along in a dance class when you don’t really understand what’s going on. Pooh is a bear who may one day spend his time earnestly tracking the footprints of a Woozle only to gradually realize that the footprints are in fact his own. He’s also a bear who sizes up the situation and the available assets and then thinks to use an upturned umbrella as a ship to float across the flooded forest floor and rescue Piglet. (Not all endeavors go so well. This is a good time to warn Pooh readers against trying to float up to inspect a live beehive by holding onto a balloon.)

Pooh and Christopher Robin are proud of Pooh’s stroke of umbrella genius, just as they are proud when, after they’ve set out to find the North Pole, Pooh indeed finds it, in the Wood. The sign that Christopher Robin ties to that pole as he plants it upright in the forest floor—

NORTH POLE

DISCOVERED BY POOH

POOH FOUND IT 

—is his version of a parent sticking their child’s fingerpainting on the door of the fridge. A buoyant Pooh, after a consult with Christopher Robin, soon sets out to find the East Pole as well.

*

In the summer of 2025, a meme emerged across social platforms featuring Jim Cummings, who has been the voice of Winnie-the-Pooh since 1988. Cummings is now 72, and, in the meme, he holds his infant grandson on his lap. In a soft, faintly husky tone—Poohlike, to be sure—Cummings says to the baby: “You’re braver than you believe, smarter than you seem, and stronger than you think. And cute as a button.”

It’s an adaptation of a line delivered by Christopher Robin in the 1997 movie Pooh’s Grand Adventure: The Search for Christopher Robin. When Christopher Robin says it in the movie, he does so as part of an attempt to brace Pooh for what the future may bring. “Pooh bear,” Christopher Robin begins. They are playing together on the branches of a tree, and evening has set in. “What if, someday, there came a tomorrow when we were apart?”

The notion is so alien to Pooh (you try imagining a tomorrow when oxygen has been entirely removed from the atmosphere) that he can’t comprehend it. “As long as we’re apart together, we shall certainly be fine,” Pooh says.

Christopher Robin giggles but presses on. “Yes, yes, of course. But if we weren’t together. . . . If I were somewhere else?”

The scene moves along, with Pooh catching fireflies in the waning light, and leads to the braver/smarter/stronger adage. But the point has now been made. Tomorrow will come. It turns out that within all the comfort and warmth, there is indeed a dagger of cruel truth beneath the surface in Winnie-the-Pooh, the same cruel truth that finally undoes every happy childhood: It ends. ▪

Here are a selection of images that touch on the rich narrative celebrated in LIFE’s new issue Winnie-the-Pooh: The World’s Most Wonderful Bear, available at retail and HERE.

Cover images: TGlyn Jones/Alamy; (inset) © Ernest H. Shepard/BuyEnlarge/ZUMA Press; (stock) Toru Kimura/Getty Images; enjoynz/Getty Images

A.A. Milne with his son, Christopher Robin, and the stuffed bear Christopher Robin originally called Edward. The early Winnie-the-Pooh short stories were based on tales Milne made up to entertain Christopher Robin.

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E. H. Shepard, here in 1976, was a prolific painter before he turned to illustration. He modeled his drawing of Winnie-the-Pooh after his own son’s bear, called Growler.

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Christopher Robin and Pooh had each other’s back in this illustration from A.A. Milne’s first Winnie-the-Pooh book, which came out in 1926.

© Ernest H. Shepard/BuyEnlarge via ZUMA Press Wire

Pooh, Piglet and Christopher Robin from A.A. Milne’s 1926 “Winnie-the-Pooh,” the first illustrated book with these characters.

ZUMAPRESS.com

Pooh met Tigger in Milne’s second collection of Winnie-the-Pooh stories. The illustration is by E.H. Sheppard.

ZUMAPRESS.com

Pooh and Piglet in A.A. Milne’s 1926 collection The House on Pooh Corner.

ZUMAPRESS.com

Ernest Shepard in 1969 (opposite). In addition to the Pooh books, he illustrated children’s classics such as The Wind in the Wilows and The Secret Garden.

David Montgomery/Getty Images

This 2009 novel picked up where the Milne stories left off.

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This rare Winnie-the-Pooh book featured an inscription from author A.A. Milne asking for artist E.H. Shephard to decorate his tomb.

Peter Macdiarmid/Getty Images