This is only the third time that Walt Disney Animation Studios produced a sequel to one of their films from the Disney Animated Classics canon in-house. The previous instances are as follows: The Rescuers Down Under (1990) followed The Rescuers (1977) and Fantasia 2000 (1999) followed Fantasia (1940).
While Disney has made many Winnie the Pooh movies, this is only their second to be produced by Walt Disney Animation Studios. All of their other Winnie the Pooh movies, both those released direct to video/DVD and those released theatrically, were produced by DisneyToon Studios and thus are not considered to be official sequels.
This was the last film from Walt Disney Animation Studios where the characters were drawn by hand. Beginning with the next film Wreck-It Ralph (2012) (and other movies after that.) The studio now does computer animated films.
Some scenes in the original movie trailer like Tigger bouncing into Pooh, Eeyore all alone, Owl explaining about his family, Pooh talking to his tummy, the red balloon floating around the woods and the whole gang walking in a parade were all not included in the actual movie.
The opening song features a slightly changed Hundred Acre Wood map, much like the original film. At the bottom of the map, it says, "Drawn by me" (implying Christopher Robin). On the second page, it says, "With help from Mr. Shepard." The original artist of the Winnie-the-Pooh books was E. H. Shepard.
The Winnie the Pooh stuffed bear which appears in the beginning of the film was made by Burny Mattinson's wife Sylvia while the Tigger, Piglet, Kanga, Roo and Eeyore stuffed toys were made by the Disney Store.
Jim Cummings and Tom Kenny who voiced Pooh, Tigger and Rabbit in this film used to work together on the show CatDog (1998) as the Title Characters. They also worked together on The Powerpuff Girls (1998) as The Mayor of Townsville and Fuzzy Lumpkins respectively.
John Cleese who voices the narrator for this movie used to be the narrator for the Mickey Mouse Works (1999) episodes The Nutcracker, Around the World in 80 days, A Midsummer's Nights Dream and Mickey's Mechanical House.
Tom Kenny stated in interviews that he was not asked to do an impersonation of Ken Sansom's voice for Rabbit. He was quite happy about this, since he doesn't consider himself a good impressionist and therefore tends to avoid soundalike roles.
John Lasseter the executive producer of the movie and Bud Luckey the voice of Eeyore both work at Pixar Animation Studios where they worked on the film Toy Story (1995) and other projects. Bud Luckey also starred in the two Pixar movies The Incredibles (2004) as Rick Dicker and in Toy Story 3 (2010) as Chuckles the clown.
As of December 2016, this is the only Traditionally Animated and G Rated Disney Animated Feature Film released during the 2010s. All others released during that decade are Computer Animated and PG Rated.
This is the first Disney movie to have songs written by Kristen Anderson-Lopez and Robert Lopez. Their next two Disney films for writing songs were Frozen (2013) 2 years later and Coco (2017) 6 years later (as Coco (2017) is the duo's first Disney movie for writing songs that's made by Pixar Animation Studios and not made by Walt Disney Animation Studios.
The last Winnie the Pooh film to be a hand drawn animated film and the last theatrical Winnie the Pooh film until Christopher Robin (2018) which will be the first Winnie the Pooh film to be live action. Only Jim Cummings, Kristen Anderson-Lopez and Wyatt Dean Hall reprise their roles for that film as Pooh Bear, Kanga and Roo respectively, whilst the other characters have different voice actors from their animated appearances (eg. Nick Mohammed voices Piglet instead of Travis Oates).