While having just entered the public domain as of 2022, demonstrated by the bizarre existence of Winnie the Pooh: Blood and Honey, A.A. Milne's immortally beloved silly old bear has almost entirely become synonymous with the Disney version. Practically an entire franchise in its own right, Disney’s Winnie the Pooh has strived across film and TV adaptions to welcome viewers into the world of the Hundred-Acre Wood for adventures that invite the simple innocence of a child’s imagination to reign as poetic and profound as any grand epic. Apart from a slew of toys, stage shows and off-kilter cable after-school specials, what Disney’s take on the character offers the most is a sense of unconditional joy, love and comfort, as any proper stuffed bear should.
Here are the films of Disney’s silly old bear ranked from “oh bother” to “something sweet”:
7. Christopher Robin (2018)
The only fully live-action film to feature Disney’s bear of very little brain, Christopher Robin is largely a film of very little subtlety. Ewan McGregor stars as grown-up Christopher Robin, now a workaholic absentee parent, as he is called back to the Hundred-Acre Wood to help find his missing stuffed animal friends and rekindle his childhood spirit. The film borrows from the themes explored in Mary Poppins and Steven Spielberg’s Hook, but lacks the joyful sincerity or clever introspection in telling the story of a grown man rediscovering his childhood. The classic characters themselves, rendered in eerily uncanny CGI, are used more to guilt-trip Christopher Robin for growing up and hammer in the film’s message, culminating in a third act that lacks the warmth and closure of other Pooh stories.
6. Piglet's Big Movie (2003)
Piglet’s Big Movie has the impact and plotting of a typical episode of one of the many Winnie the Pooh TV series. While overhearing that his friends think him “too small” to help with anything, Piglet (John Fiedler) disappears into the woods while Pooh (Jim Cummings) and the rest of the gang embark on a journey to find him and apologize. The film is of low-stakes and basic structure even by Pooh standards, but remains true to the likability of its characters in a harmlessly good-natured attempt to give the big spotlight to little Piglet.
5. Pooh's Heffalump Movie (2005)
By its wholesome nature, the Hundred-Acre Wood does not offer much in the way of villains or antagonists. The closest Pooh has had to an overtly evil character was the mythologized Heffalumps and Woozles, who steal honey and run amuck in psychedelic splendor. In Pooh’s Heffalump Movie, the gang is introduced to Lumpy (Kyle Stanger), a baby Heffalump who befriends Roo (Nikita Hopkins) and helps disarm the gang’s preconceived notions of Heffalumps. The film teaches a vitally important lesson scarcely touched upon in other Pooh titles of not dismissing people based on stereotypes and prejudices and boldly holds the characters up to task to grow passed and embrace what they initially feared as a welcome new friend. Coupled with the likably cute new character of Lumpy himself, the film’s stellar animation holds it up to the Pooh standard of entertainment.
4. Pooh's Grand Adventure: The Search for Christopher Robin (1997)
Pooh’s Grand Adventure was the first full-length feature since the original film 30 years prior and the first one to be done by Disney TV Animation. Much like the other straight-to video sequels, the precedent this film had to live up to as the follow-up to the original Disney classic was daunting, but the greatest advantage was that these characters and their world never really went away thanks to various TV shows and specials. What the film was challenged with and greatly succeeded in was placing these simple characters in much higher emotional stakes than they had experienced before, as they embark on a dangerous journey to find their dear friend. As the first official film sequel to Disney’s Winnie the Pooh, Grand Adventure delivers exactly as its title promises and stretches the limits of what it can put its characters through.
3. The Tigger Movie (2000)
The idea of giving Tigger (Jim Cummings) his own movie in The Tigger Movie may come across as redundant on paper, but in execution amounts to a freshly human outing for the Hundred-Acre Wood gang. Inspired by the idea of a family tree, Tigger decides to invite all of his bouncy kin over for a big family reunion, the only problem being that since he is the only one, they are nowhere to be found. Told with some of the best animation to come out of Walt Disney Animation Japan and songs by Disney legends Robert and Richard Sherman, the film’s exploration of what it means to have family and where it can be found is a poignant one and told in a resonantly vulnerable way through its characters, making it a surprisingly top-tier and terrific Tigger tale.
2. Winnie the Pooh (2011)
There is an enormous amount of heart poured into 2011’s Winnie the Pooh, which sought to emulate the look and feel of the original shorts that Pooh debuted in. While the story itself retreads territory from both previous Pooh films and the original books, the film indulges in the comfort of its own familiarity and elicits charming new memories with old friends. To date, this is the last traditionally hand-drawn film to come out of Walt Disney Animation Studios and that prestige is carried throughout the film as the artistry of Disney character animation is on full display here, portraying the classic characters with an expressiveness and fluidity not seen in years. While it is a humble and simple little film, it offers a wholehearted embodiment of what Winnie the Pooh has meant to the studio and to audiences across have a century.
1. The Many Adventures of Winnie the Pooh (1977)
The original classic. Initially released as three separate featurettes released across 1966, 1968 and 1974, the compiled Many Adventures of Winnie the Pooh has remained one of the most prevalent Disney landmarks and a beloved family classic. Everything about this film is classic Disney to its very core. The iconic songs from the Sherman brothers, the painterly storybook backgrounds, the endearing and cozy time spent with its characters all created an unmistakably Disney masterpiece from the era in which Disney animation was at its cultural peak during Walt’s era. There is no finer piece of Winnie the Pooh media from across its decades as a Disney icon that perfectly demonstrates the wholesome and innocent appeal of the character and his world.