The Movie:
- Christopher rescuing Eeyore from the waterfall. While also a funny moment, it's impressive as he prepares to swim in the river in order to save Eeyore.
- The toys/animals all realize that Christopher Robin needs their help. Without hesitation, Pooh, Piglet, Tigger, and Eeyore go and try to find him in the real world.
- Madeline takes a train all by herself and joins with the toys to return her father's papers to him.
- Madeline managing to distract a policeman so that she, Pooh, Piglet, Tigger, and Eeyore can sneak off and stow away in some crates in a Winslow company truck.
- Christopher winning over Winslow Sr. with his presentation and completely showing up Giles in front of his father. He also manages to slip in increasing employee benefits to include paid vacation by telling his boss that people who are able to take vacations will need luggage. Winslow luggage.
- Christopher stands up to Winslow Jr., calling him a Woozle. It's a heartwarming moment where he rediscovers his inner child, but he also tells his shitty boss that he's a shitty person.
- Winslow Sr., calling out his own son when it's revealed he'd been golfing over the weekend instead of working.
Winslow Sr.: Now I've not heard of a Woozle before son, but by the sound of it, you are one.- Out of everyone, it's Eeyore who throws a Death Glare at Winslow Jr. once his duplicity is revealed. It's so emotive that even Giles realizes there's more to Eeyore than meets the eye.Giles: That donkey was staring at me.Winslow Sr.: A donkey staring at you? Clearly, it's you who have lost your marbles.
- You know a line has been crossed when Eeyore, the naysayer and doom-monger, is the one giving you the death glare.
Behind the Scenes:
- A major one for Jim Cummings. Except for Eeyore, who's voiced by American actor Brad Garrett,note all the other residents of the Hundred Acre Wood were replaced by well-known UK actors. But not Pooh and Tigger, they're voiced by Jim Cummings as usual, his performances are that iconic.
- And even better? Chris O'Dowd was originally going to play Tigger, but was replaced by Cummings because he tanked in the test screenings. Yep, the audience wanted Cummings, and they got him.
- The legendary Richard M. Sherman wrote three songs for the film. He's been writing songs for Disney with his late brother since The '60s.
