Winnie the Pooh is one of the most recognizable pop culture figures in the world, alongside Mickey Mouse, Bugs Bunny, and Superman. Created by author A.A. Milne, the character has appeared in a number of stories, and to audiences outside the United Kingdom is most commonly associated with Disney. Disney acquired the licensing rights to Winnie the Pooh in 1961 and released a series of short films about the character. Since then, Pooh Bear and his friends have become some of the most recognizable characters in the Disney library, and Disney has capitalized on their popularity. The studio has released six films theatrically and several television series directly based on the characters' adventures. Merchandise for Winnie the Pooh is everywhere and still sells after all these years.
The U.S. copyright on Winnie the Pooh expired at the end of 2021 meaning the character Winnie the Pooh entered the public domain, ending Disney's exclusivity on the character (although they do own their specific artist depiction). Following the announcement, a low-budget slasher film titled Winnie the Pooh: Blood and Honey was put into production. It is likely there will be a number of Winnie the Pooh feature films in the near future following the character entering the public domain (though it's worth noting the UK copyright does not expire until 2027, 70 years since Milne's death). With that in mind, these are all the current theatrically released Winnie the Pooh movies ranked.
7 Piglet's Big Movie
Released in 2003, Piglet's Big Movie is one of three theatrically released Winnie the Pooh films by Disneytoon Studios, a former animation division that specialized in direct-to-video animated projects, some of which occasionally got a theatrical release. After the box office success of The Tigger Movie, the studio opted for another big-screen movie based on a Winnie the Pooh supporting character, this time Piglet.
While maintaining the cute charm in the Disney Pooh stories, the film does feel more like a direct-to-video movie than a theatrical story, as a bulk of the film tells different stories about Piglet, giving the movie the feeling of various episodes of the popular New Adventures of Winnie the Pooh series strung together with a framing device. While this was likely an attempt to go back to the roots of the franchise in The Many Adventures of Winnie the Pooh, it comes off more as an attempt to hide the fact they couldn't find a whole narrative as they did with Tigger. This was a trick Disneytoon Studios often employed with direct-to-video films like Tarzan & Jane and Atlantis: Milo's Return, which were just episodes of the animated series strung together. Still, after so long as a supporting character, it is nice to see Piglet get the spotlight and to highlight that Piglet is braver than he or even the audience might think.
6 Goodbye Christopher Robin
The only film on the list not produced by Disney (although technically now is, due to Disney's acquisition of distributor Fox Searchlight), Goodbye Christopher Robin is a biographical film about author A.A Milne (Domnhall Gleeson) and the story of how the author came up with the Winnie the Pooh story and the relationship between the author and his son, the real-life Christopher Robin. Directed by acclaimed English filmmaker Simon Curtis (My Week With Marilyn), Goodbye Christopher Robin is less a movie about the creation of Pooh Bear and more an exploration of the complicated parent-child relationship that stems from building one's popular character of a real-life child and the impact it has. While it may not get as deep into the conflict as the real-life story, it does touch upon how the books impacted the real-life Christopher Robin. Similar to Disney's own Saving Mr. Banks, which featured a reference to Disney's depiction of Milne's Winnie the Pooh, both films are about how these simple creations can have large impacts on the world.
5 Pooh's Heffalump Movie
The last Winnie the Pooh movie released in theaters by Disneytoon Studios and the last theatrically released film until Winnie the Pooh six years later, Pooh's Heffalump Movie might not be a groundbreaking film, but it does spotlight a long-overlooked element of the series. The Winnie the Pooh franchise is one of the few without a villain, although the imaginary threat of Heffalumps and Woozles has hung over the series with a fun sense of danger. However, with Pooh's Heffalump Movie the franchise finally introduces a new character to the series (a first since Jessie the bluebird in The New Adventures of Winnie the Pooh) in the form of the baby Heffalump Lumpy and attempts to show that this creature the franchise has used as a monster is just misunderstood.
The central protagonist of the story is Roo who, as the only kid in the 100 Acre Woods cast, in many ways acts as the character kids can latch onto. It is his compassion and innocent worldview that allows for peaceful first contact with a Heffalump and his friendship teaches the others an important lesson in tolerance.
4 The Tigger Movie
Released in 2000, The Tigger Movie was the first Winnie the Pooh movie released theatrically since The Many Adventures of Winnie the Pooh, the first Disneytoon Studio film in the Winnie the Pooh franchise, and attempted to break the mold by being a full-length feature film as opposed to a collection of shorts. Originally intended as a direct-to-video movie, the film was bumped up to theatrical after then Disney CEO Michael Eisner heard the Sherman Brother's songs for the film. It is also notable as this marks Jim Cummings officially taking over the role from original Tigger voice actor Paul Winchell, who left the project due to his voice being considered too raspy.
The Tigger Movie keeps the same charm as the other Disney Winnie the Pooh stories by being light and charming, but it also adds higher emotional stakes and easily the darkest and most intense climax to any film in the franchise. All the Winnie the Pooh films are about imparting lessons to young audiences, and with The Tigger Movie kids are taught an important lesson early on: family is not just blood, but it is the friends in your life that love you.
3 Winnie The Pooh
Winnie the Pooh from 2011 was the character's grand return to cinema and was only the second time Walt Disney Animation made a sequel to one of their classic films, following The Rescuers Down Under 20 years prior. While it seemed Disney and every other animation studio was going to pivot entirely to CGI, Winnie the Pooh was one more attempt at giving 2D animation a big push. One wonders what might have been had Disney not decided to release Winnie the Pooh on the same weekend as the final Harry Potter film.
While the movie was a box office disappointment, it received critical acclaim and in many ways is an underrated gem in the Disney catalog. In many ways, it is an important film for the following decade at Disney, as it was the first time Kristen Anderson-Lopez and Robert Lopez worked with Disney before they'd go on to write the hit songs for Frozen, Frozen 2, and Pixar's Coco, while director Don Hall would go to co-direct Moana and direct Big Hero 6, Raya and the Last Dragon, and the upcoming Strange Worlds.
An amazing teaser trailer set to Keane's Somewhere Only We Know very much set the tone for the film, a warm nostalgic look back at a childhood icon that older audiences could enjoy like the return of an old friend, while also being a great new entry point for younger audience audiences. With an original song So Long and a recording of the classic Winnie the Pooh theme by Zooey Deschanel, the film has a kind summer morning glow to it that reminds the audience of what it was like to be a child when the world was much simpler.
2 Christopher Robin
Disney has found great success remaking their classic animated films, and it made a certain amount of sense to bring 100 Acre Woods to live-action. 2018's Christopher Robin stands very much apart from the other Disney remakes. Technically, Christopher Robin is a sequel to The Many Adventures of Winnie the Pooh, with the openings being a remaining of that film ending and following an adult Christopher Robin (Ewan McGregor) having gotten lost in work and struggling to balance his work and family, all until Winnie the Pooh returns and sends Christopher Robin on a journey back to 100 Acre Wood to find his old friends and also rediscover his youth.
While Christopher Robin is a movie kids can enjoy, the film is in many ways targeted at an older audience who grew up with Winnie the Pooh in some shape or form in their adolescence. It is a much more melancholy film, touched by nostalgia at the sadness of growing up and losing one's childhood, and mixes both the classic Disney interpretation of the characters with an aesthetic choice meant to honor the original source material. If 2011's Winnie the Pooh gives the feeling of a youthful summer day, Christopher Robin is a reflection of it, as it has a more washed-out palette meant to signify the passage of time, which has always been the greatest source of conflict in the Winnie the Pooh universe. Christopher Robin in many ways feels like the nice return of an old friend, and a reminder that sometimes one can go home.
1 The Many Adventures of Winnie The Pooh
Walt Disney's original plan was always to release a Winnie the Pooh feature film, however, the filmmaker decided to release a series of shorts to familiarize audiences with the characters. The studio released three shorts, 1966's Winnie the Pooh and the Honey Tree (released shortly before Walt Disney's death), 1968's Winnie the Pooh and the Blustery Day, and 1974's Winnie the Pooh and Tigger Too. The three shorts were then collected into a theatrical release, and in 1977 Disney released The Many Adventures of Winnie The Pooh as their 22nd animated feature film and included a new ending with Winnie the Pooh and Christopher Robin to give it a sense of competition.
The Many Adventures of Winnie The Pooh stands as one of the best films released by Walt Disney animation, as the film breaks many conventions of Disney animated films. There is no villain in the story, but it is much more a film focused on mood and characterization. That focus on character has been the film's greatest strength for years, as after all this time audiences still return after all this time.
Audiences may still be hard-pressed to name all seven dwarves in Snow White or the children in Peter Pan, but everyone knows Pooh, Piglet, Tigger, Eeyore, and the rest of the 100 Acres Woods gang. These characters are all so lovable and well-written that they have been able to tell stories across various series, films, and storybooks. The film's final moment, of Winnie the Pooh and Christopher Robin, is a bittersweet goodbye to childhood and works as a beautiful articulation of why this franchise has endured for so long: "Wherever they go, and whatever happens to them along the way. In that enchanted place on top of the forest, a little bear will always be waiting".