When compared to all the other animated Disney classics, what's unique about Winnie-the-Pooh is that its appeal lies solely in its characters. With this franchise there was never an overarching story featuring any kind of moral or princess or triumph of virtue over wickedness. It was just an odd assortment of animals living in community, a variety of personalities with everyday social friction. The Many Adventures of Winnie-the-Pooh (1977) is not truly a feature film but rather a collection of three shorts produced in the preceding decade: Winnie-the-Pooh and the Honey Tree, Winnie-the-Pooh and the Blustery Day, and Winnie-the-Pooh and Tigger Too. Pulled from the literary genius of A.A. Milne's works of the 1920s, these characters based on author's son Christopher Robin Milne's stuffed animals made the transition to cartoon and became truly alive. Peter Pan, Aladdin, Cinderella, Alice in Wonderland, The Jungle Book... these Disney tales are all lifted from classic literature and feature great characters too, but it's only through the central plot that their traits show through. They don't play off each other but only off their current situation and conflict; there's no story to tell when society no longer has a need for Robin Hood to steal from the rich and give to the poor. Winnie-the-Pooh takes a different approach to entertainment and has continued to deliver high caliber, fresh episodes in each decade since the series' Disney incarnation in the 1960s.
While everything successful about Winnie-the-Pooh can be attributed to its memorable characters and their appearances in approximately 100 featurettes/episodes when counting the '80s/'90s television series, it was probably no surprise that Disney would eventually make a proper full-length movie. Cue The Tigger Movie in 2000, the first of what would be several theatrically released full-length Winnie-the-Pooh feature films. Ditching all personified insects and Gopher, the movie keeps only those characters written by A.A. Milne and even minimizes Pooh, Piglet, and Eeyore considerably, but hey, this is The Tigger Movie for a reason. If you like Tigger, Roo, and Kanga you'll see quite a lot of them, and there are some great Rabbit foil moments as well. The premise is that Tigger is in search of his family: the other Tiggers he believes exist despite his time-old claim that he's "the only one". It's beautifully simple and well-played over the course of its 78 minute run-time with little distraction. What I really love about The Tigger Movie is that it stretches the boundaries and surreality of the 100 Acre Woods in a thought-provoking way as Tigger carries out his quest to find his relatives. It's predictable in an appropriate way and hits all the emotions in key moments of the journey (excitement, disappointment, anger, sadness, fear, love). Once again all the voice actors are uncanny in their likeness to the originals which is another subtle ingredient to the success of the Winnie-the-Pooh franchise. The animation is incredibly detailed, with sharp character models and tastefully subdued color pallets. There's actually a sense of focus in the often blurry outdoor background, making for great visuals enhanced by blowing leaves and other extraneous objects in motion. There are some new songs which the characters sing but nothing too unbearable for adults to sit through.
Disney sequels have a reputation of falling short, but unlike the others Winnie-the-Pooh is free from the common pitfalls. While its characters certainly excel when explored in plots under the short-story format, the opportunity for a traditional full-length animated film will always exist if there's a strong enough idea that's built around the characters and not the other way around. In this sense The Tigger Movie does a great job and sets the standard high for any movies that would follow. The message about family is cliche, but the fact that there's a deeper meaning and purpose of the film is why they made it. That and to milk debatably their best franchise for some more money.