Winnie the Pooh is one of the most popular franchises for small children and is one of Disney’s top brands with an estimated $80 Billion total sales since its inception. One market in particular Winnie the Pooh was well versed in was the home video market. 

The series did have two films made by Disney’s feature animation group in 1977 and 2011, but during the “Disney Sequel Boom” of the Late 1990s – Early 2000s Winnie the Pooh received nine films from Disney Toon Studios. There were even three films released between 2007 – 2010 that tied into the My Friends Tigger & Pooh tv series.

So out of those numerous films let’s take a look at five of them worth a watch.

– The Tigger Movie (2000)



The first Winnie the Pooh film to specifically follow a character other than Pooh was The Tigger Movie. This film follows Tigger as he feels not so happy being the only Tigger in the hundred acre wood. After his concerned friends send an anonymous letter to Tigger he believes that there are other Tiggers after all and they’re coming to visit him. His friends then dress up as Tiggers to try and make him happy. In the end Tigger realizes that he already had a family, those being the other inhabitants of the Hundred Acre Wood.

– Piglet’s BIG Movie (2003)



Piglet’s Big Movie is about how Piglet feels left out. He later decides to leave the Hundred Acre Wood due to neglect. Once his friends notice that he’s missing they find his scrap book. From his book they read three stories where Piglet made a “BIG” difference for being such a small animal. The group then goes out to find Piglet before something bad happens to him. In the end Piglet returns home safely and you learn that you never know what you have until it’s gone.

– Winnie the Pooh: Springtime with Roo (2004)

One of the different holiday themes films, Springtime with Roo, follows Roo and friends as they are on their way to celebrate Easter at Rabbit’s house. Upon arrival Rabbit seemingly forgets about Easter until they discover he is intentionally avoiding it. Tigger, trying to convince Rabbit to bring Easter back, goes back in time to see why Rabbit is so upset. The film is an Easter themed take on the classic A Christmas Carol story (VeggieTales did the same thing). In the end Rabbit realizes the error of his ways and returns the beloved holiday back to the Hundred Acre Wood.

– Pooh’s Heffalump Movie (2005)

Pooh’s Heffalump Movie primarily focuses on Roo as a Heffalump is scaring the residents of the Hundred Acre Wood. Roo ventures out and finds the Heffalump, who turns out is just a little kid like him named Lumpy. The two become quick friends, but through a misunderstanding the others believe Lumpy kidnaped Roo. In the end everything is resolved and we are taught a lesson in not judging others based on appearances. 

– Pooh’s Grand Adventure: The Search for Christopher Robin (1997)

Perhaps one of the best Winnie the Pooh films of all, Pooh’s Grand Adventure follows Pooh and friends as they venture out on a quest to find Christopher Robin after believing he was abducted by a creature called the “Skullasaurus”. On their journey each member learns something about themselves and confront their fears to try and rescue Christopher Robin. A wonderful heartfelt film about friendship and loyalty.

These films are great not just for children, but for those who are looking for simple stories with fantastic characters, to give you a wonderful experience, that makes you feel like a kid again. All these films are currently available on DVD and Disney Plus.