It's obvious watching this movie that they had a much smaller budget than in other Winnie the Pooh movies, even compared to the other direct to VHS movies. They reuse clips from a decade older Winnie the Pooh Christmas special, and the new animated story they are trying to tell is pretty ROUGH to say the least.
That being said, the movie starts with one of these newly animated sections, and it's fine.
Unfortunately it serves as an introduction to the first half of the movie, where they heavily reuse old clips from "Winnie the Pooh and Christmas Too" from 1991. These segments are obviously older, but at the same time it's clear that more time and effort was put in to animating them. However they are edited together in a way that is a little confusing and removes a lot context and charm from the original. It also doesn't really match the tone or flow of the rest of this movie, but that has more to do with how the new sections were animated than any fault of the original movie.
I grew up watching "Winnie the Pooh and Christmas Too" and would recommend skipping this new movie entirely and watching the original; except the original is a bit hard to find if you don't already have it on VHS (and have a VHS player still). While this new movie is on Disney+, as of writing this "Winnie the Pooh and Christmas Too" is only available for rent on YouTube or Amazon Prime Video. If you are willing to pay $3.99 or have the original through some other means, then I highly recommend checking that movie out, it was done better there.
The rest of the movie consists of a newly animated story that moves on from Christmas and focuses on New Years and New Years resolutions. Christopher Robin tells Pooh about New Year's resolutions, and wants to throw a New Year's party. Pooh decides to invite himself over the Rabbit's place to snack on some honey and ask Rabbit if it's okay to have the New Year's party at his place. When Piglet, Tigger, and Eeyore show up, Pooh tells them there's a party, even though he had yet to tell Rabbit this until that very moment. Of course they trash the place and, Rabbit scolds them all and decides to leave the Hundred Acre Wood. Pooh, Piglet, Eeyore, and Tigger all then make New Year's resolutions to change in order to please Rabbit: Pooh will never eat honey again, Piglet will never be scared again (now sure why Rabbit is so upset a Piglet tbh but alright), Eeyore will always be cheerful, and Tigger will never bounce again. You can guess where the story goes from there and the lesson about not changing who you are too much just for others.
Immediately the payoff of what was set up in the intro to the entire movie is tonally just off. They break out into two separate original songs, when "Winnie the Pooh and Christmas Too" had exactly 0 songs. There are also more original songs to come later, and none of them last for very long or are particularly good. Pooh's characterization is also different from the original: he forgets where he hid Piglet's Christmas present and searches for it for a whole week before forgetting about it. He has always been a bit absent minded and honey hungry, but they push it to an extreme that just doesn't feel right for his character. And when the characters have to change who they are for their New Year's resolutions, it feels a bit forced. For some reason it can't just be "Tigger isn't happy if he can't bounce", or "Piglet can get into danger if he isn't afraid of anything" it becomes "Tigger acts like Piglet without his bounce, and Piglet acts like Tigger when he's no longer afraid". Similarly Pooh and Eeyore are portrayed as counterparts,
: Pooh becomes sad like Eeyore without honey, and Eeyore eats honey, stands on two legs, and wears a shirt like Pooh when he's trying to be happy? Not going to lie, "cheerful Eeyore" is unsettling, it's scarier than a number of horror movies I've seen.
I think the idea could have worked better in concept, but the execution did not work. A lot of that has to do with the animation of the new sections, which is cheap looking and removes a lot of the charm of these characters. The characters feel like they are disconnected from the background they inhabit, like they are paper cutouts over a static backgrounds. At times you can tell where character models have sections that don't move and sections that willove as the movie parts are colored differently than the static parts. It's definitely not the worst animation I've ever seen or anything, but it's the type of animation that screams "HELP!!! We are the animators, and we need more staff, more money, more time to work on this, something! Please help!". I can feel the crunch time they were put through through the animation.
I also think the juxtaposition of what is essentially two separate movies smashed together here is also what makes this all a bit jarring. I suspect though that I wouldn't be complaining as much here if instead this New Years segment was allowed to be it's own 30 minute special, instead of being smashed together into an hour long double feature. I think if there had been one New Year's special which started off with emphasizing Pooh, Piglet, Eeyore, and Tigger's flaws right off the bat, when Rabbit scolds them and they make their resolutions it wouldn't feel so off. The Pooh and friends in "Winnie the Pooh and Christmas Too" are much more benign and their character traits less extreme, to the point where it feels odd alongside their behavior in the new segments.
That being said, there are things I like about this movie. The New Year's concept is unique, not a topic that a whole lot of children's animated movies usually cover. Some of the charm still manages to come through, despite their best efforts. And I think the lessons that it is trying to teach (first half: the effort we put into our friends/loved ones is the best gift of all; second half: don't try to change for other people, only change for yourself) are good lessons for kids to learn. Overall, I gave this movie a five not because it's a egregiously terrible movie, but because the two stories forced together in this movie should be split right down the middle (just like 5 is 10 split down the middle)
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