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Ranking Winnie the Pooh Films

Winnie the Pooh is a classic A. A. Milne character that has enjoyed his status as a children’s icon for decades now, and thus he has received quite a number of films, most coming from Disney. Some of these are smaller in scale, some belong to the Disney canon, and there is one non-Disney as well. I included all seven of them on my list with the live-action pictures being present as well.

7. Piglet’s Big Movie

Piglet’s Big Movie got the last spot as the worst of the three Disneytoon Studios Pooh movies. All three are admittedly of the similar quality, but this one is too episodic and too much sacrificing many of its characters for just the titular one. It’s charming and old-fashioned for sure, but overall it was not great.

6. The Tigger Movie

This one shares the same problem as the aforementioned flick – Tigger should be a supporting character, and by giving him a whole movie with a lead role, they sacrificed a lot of his appeal and humor. The movie is heartwarming and sometimes fun for sure, but the second act is needlessly prolonged and boring for such a simple plot.

5. Pooh’s Heffalump Movie

Easily the best of these three is Pooh’s Heffalump Movie. It demystified the Heffalumps way too much for my liking for sure. It also fell into a typical children’s message movie trap in the third act. However, the beginning is excellent and the musical numbers are actually rather solid for this type of film.

4. Goodbye Christopher Robin

Goodbye Christopher Robin is the only non-Disney film on this list. It depicts the darkness behind one of the most beloved children’s books so well and it makes for a really fascinating watch. It showcases the negative aspects of fame and how it can destroy lives and families and is thus thematically very relevant today. It’s a surprisingly good, underrated biopic.

3. Winnie the Pooh

This often overlooked, very good Disney canon film certainly is very low in stakes and is simplistic and short, but it’s so incredibly heartwarming, old-fashioned and traditional in approach that you can’t help but enjoy it tremendously. I loved the hand-drawn animation, many characters got their moments to shine and the humor is surprisingly terrific.

2. Christopher Robin

Underrated is the name of the game once again as Christopher Robin is easily one of the best live-action Disney films in recent years. It has a typical, cliched family film third act, but everything else is excellent as the tonal shifts from depressing to sweet are well handled, and the characters are all excellent. It’s an incredibly touching movie.

1. The Many Adventures of Winnie the Pooh

And the number one just has to be this classic 1977 Disney film, the most quintessential of all Pooh films. The flick is, like many on this list, overly episodic and uneven. But it benefits from excellent characterization and voice work, strong animation and a very solid soundtrack with some instantly memorable musical numbers. Most importantly, it features one of the greatest, deepest endings in the entire Disney canon. It’s an underrated gem from the studio’s weaker decade.