In 1926, A. A. Milne (with the help of E. H. Shepard) crafted a children's book about a boy who imagined his stuffed animals to life and played with them in the Hundred Acre Wood. The idea was based on his son, Christopher Robin Milne, who had a significant love for his own stuffed animals. And just like Milne's own son, of all the animals in the book, there was one who Christopher Robin loved most, the titular bear, Winnie-the-Pooh. The book quickly became a success and both Milne and Shepard got to work on the subsequent 1928 novel, The House at Pooh Corner. Pooh became a household name during the 1930s to 1950s, garnering much success through toys, radio shows, stage plays, board games, etc. And then in 1961, the rights to Winnie-the-Pooh were sold to Walt Disney Productions, for which they had been the sole copyright holder until Jan. 1, 2022, when the character entered the public domain in the United States.

In those six decades that Disney held exclusivity over the characters of the Hundred Acre Wood, they produced many animated shorts, films, shows, toys, games, books, and so much more that have not only brought so much life to the franchise but have also touched the lives of generations of children and adults. Many of the films especially have stood the test of time and reside in the hearts of the many that grew up with them. And now that the original book has entered the public domain, the floodgates have been open for anyone to use these characters however they please, like the upcoming slasher retelling, Winnie-the-Pooh: Blood and Honey (2023). Regardless of whether you're excited about the film or not, the fact that anyone can make a Winnie-the-Pooh film now means that we'll be seeing a lot more of these kinds of horror parodies and cash-grabs in the future. So, instead of letting the fate of a low-budget slasher cloud our minds, let's focus on remembering a few of the fantastic, animated films that Disney has produced about that silly old bear.

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Winnie the Pooh and the Honey Tree (1966)

Winnie the Pooh and the Honey Tree (1966)
Image Via Disney

Disney's very first animated outing in the Hundred Acre Wood (directed by Wolfgang Rietherman who'd previously directed 101 Dalmatians, Sleeping Beauty, and Jungle Book) absolutely deserves to be recognized as the wondrous little piece it is. Based on the first two chapters of the original book, Winnie the Pooh and the Honey Tree is a charming tale of Pooh Bear's quest to get honey and all the trouble that comes along with it.

The animation can seem a bit rough nowadays, but in a way, that adds to the charm and general coziness of the short. There's no imminent threat or strict plot holding the characters back, instead, the story is simple enough to let the audience live with the characters and get to know them on a much friendlier, more relaxed level. Add to that a number of catchy songs, some clever methods of interacting with the book it's based on, as well as an immediate sense of familiarity with the characters; this film set the gold standard for Disney's interpretation of A. A. Milne's creation.

The Many Adventures of Winnie the Pooh (1977)

The Many Adventures of Winnie the Pooh (1977)
Image Via Disney

Winnie-the-Pooh's first feature film is, appropriately, a collection of the three shorts that Walt Disney Productions had previously made: Winnie the Pooh and the Honey Tree (1966), Winnie the Pooh and the Blustery Day (1968), and Winnie the Pooh and Tigger Too (1974). Outside a few transitional scenes in-between each short, a whole newly animated ending, and some slight visual enhancements, the shorts remain practically unchanged from their original state. Sure, that may seem odd if you are already familiar with said shorts, but watching them all-together in this format helps to create a much more enriching experience as a loose anthology instead of just a mere collection (much like the original book). Seeing Pooh and friends spend time with each other is always a wonderful sight, and this is arguably the bear's most iconic outing in that regard. Also, that ending is about as beautiful and gut-wrenching as they come.

Winnie the Pooh and a Day for Eeyore (1983)

Winnie the Pooh and a Day for Eeyore (1983)
Image Via Disney

Six years after the feature film's release, Disney produced a fourth featurette focusing on the lovably depressed donkey, Eeyore. Thinking back over the franchise, Eeyore is often one of the more underutilized characters as he's pretty one-note in both personality and comedy, so seeing him get the spotlight here is certainly a breath of fresh air. It's nice seeing Pooh and Piglet try so hard to find the right birthday present to cheer Eeyore up, and the brief conflict that he and Tigger have leads to a kind of dynamic that we don't often see in these original shorts. This is yet another charming short that captures the same feel as the first three despite not having any of the previous staff work on it (so much so that it was even added to subsequent home releases of The Many Adventures of Winnie the Pooh).

The Tigger Movie (2000)

Tigger giving Roo his locket in The Tigger Movie
Image via Walt Disney Pictures

In a bit of a departure from the established norm, the second theatrically released animated film in the franchise was not an anthology of stories, but instead a traditionally structured narrative centered around Tigger's mission to find his long-lost (and perhaps imaginary) family. The animation is a real treat here. Being the franchise's first animated project of the 2000s, the overall look is sharp and warm while still emulating the rough sketchiness of the original shorts. And that's not even to mention how some of the song numbers (nearly all of which are catchy and inviting) play with different visual styles in creative ways. This film, despite being so unique, is a wonderful exploration of Tigger (beautifully performed by Jim Cummings) and the loneliness he often feels for being so different from the rest of the animals in the Hundred Acre Wood. And it's a testament to these characters that, even after all these years, they still have the ability to elicit some genuine emotion in new and creative ways.

Winnie the Pooh (2011)

Pooh, Tigger, and friends in 2011's Winnie the Pooh
Image via Disney

The last Winnie-the-Pooh animated feature to be released so far, and Disney's final 2D-animated theatrical film to date, 2011's Winnie the Pooh is somewhat of a return to the styling of the first movie as it's more of a thinly-veiled anthology than anything else. There certainly is more attention put into having each story flow into the next here, however, that doesn't at all take away from the more relaxed structure or leisurely (yet concise) pace. Once again, the animation, and voice work are phenomenal, bringing the Hundred Acre Wood to life in a way that hasn't really been seen before. Yet, the real standout of the film has to be the songs, all of which are fantastic and arguably stand as some of the best in the series ("The Backson Song" and "Everything is Honey" being the true stars of the show).

This film certainly isn't as emotionally poignant as some of the other ones listed; however, in terms of just being yet another wonderful and charming adventure with these timeless characters, Winnie the Pooh shows that at the end of the day, Disney's interpretation of Christopher Robin and his stuffed animals is something that truly resonates with people.