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  • Author's Saving Throw: There was a lot of negative reception to Chris O'Dowd being cast as Tigger over Jim Cummings, especially after the teaser trailer earned widespread acclaim for having Cummings reprise his role as Pooh. When the second trailer arrived, it was revealed that Cummings is indeed voicing Tigger, to many people’s delight.
  • Catharsis Factor: When Christopher Robin gives Winslow Jr. a family friendly "Reason You Suck" Speech.
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  • Critical Dissonance: A mild case; the film has a mixed-to-positive critical reception (71% on Rotten Tomatoes), but a strong 89% audience approval rating.
  • Crosses the Line Twice: Christopher Robin reunites with Eeyore as the donkey is floating down a river, at first it's played very seriously as Eeyore floats closer and closer to the impending waterfall and remakes that he'll 'be gone soon' and 'no one will notice'. Then Christopher jumps in to save his old friend and it turns out the water is ankle deep and the "waterfall" goes up to his knees; hey, it would have been a lot deeper to a child.
  • Harsher in Hindsight: Utilised. A recurring ominous point throughout both the novels and the Disney canon is that Christopher Robin would ultimately grow up and become detached from his imaginary friends. This film shows the results in full view with Christopher now suffering the hardships of adulthood and struggling to relate to Pooh and the others again (though it also adds some light at the end of the tunnel with him and his family reconciling with his old friends).
  • Hilarious in Hindsight:
  • Just Here for Godzilla: Let's all be honest here - no one saw this movie for Ewan McGregor or his human co-stars (bar dedicated fans of Hayley Atwell), the established Winnie The Pooh characters just being here and themselves is the reason anyone is drawn to this movie.
  • Love to Hate: Giles Winslow Jr. is a childish, petty, irresponsible, emotionally and mentally manipulative Jerkass with a smug attitude and simpering smirks to rival Dolores Umbridge, making him probably the most loathsome antagonist to pop up in anything Winnie The Pooh related (in addition to being the only human antagonist in the series' history), but Mark Gatiss performs the part so well that he's as enjoyable to watch as he is insufferable.
  • Memetic Mutation:
    • The main poster's tagline, "sooner or later your past catches up with you," being accompanied by the "obi" part of the title, in another joking demand by fans for Ewan McGregor to reprise the title role in an Obi-Wan Kenobi standalone movie already.
    • Also, turning Christopher Robin's reunion with Pooh into the "Hello there" meme.
  • Moral Event Horizon:
    • Giles Winslow Jr. crosses it when it's revealed that he spent the weekend golfing instead of helping Christopher Robin work out the cost cutting at the company. It's here that it's revealed that the whole 'swimmer or sinker' spiel he gave to Christopher was nothing more than a manipulation tactic Winslow spun just to get someone else to do his work for him, all the while knowing full well that his own job security was almost assured because his father Winslow Sr. is the company founder. Quite mild compared to what you'd normally expect for this trope, but in the context of the franchise, that cemented Winslow's status as a villain.
    • Christopher Robin himself believes he crossed it at some point during World War II, and even confesses as much to Pooh. Being forced to kill countless of your fellow humans can do that to you. More pointedly, he had lost a lot of innocence he will never truly be able to regain in full.
  • Most Wonderful Sound: Pooh's voice, provided by Jim Cummings himself. There was also a lot of rejoicing when Cummings was confirmed to voice Tigger in the second trailer.
  • Narm Charm: Christopher Robin's speech in the boardroom can come across as unintentionally funny at parts, since he says 'Woozles' and 'sometimes doing nothing can lead to the best of something' in a completely serious context, with it played as an epic moment of standing up for himself. However, it comes off as a family friendly '"Reason You Suck" Speech'. It is rather cathartic when Winslow Sr. puts Winslow Jr. in his place after listening to what Christopher said along with becoming more open minded to some of Christopher Robin's suggestions.
  • Nightmare Fuel: Christopher Robin getting himself lost deep in the 100 Acre Wood after his fight with Pooh makes the movie take a sudden turn into horror. Christopher even believes they're Hefflalumps chasing after him, falls into a pit purposed to trap Heffalumps and gets knocked unconscious by a stray rock and almost drowns when the pit gets filled with rainwater, all while having a nightmare where a Heffalump appears in the water and drags him away with its trunk as he tries to escape it, all the while hearing voices that make it clear that this Heffalump is a metaphor for all of his all-too real troubles.
    • In the midst of correcting Pooh in how to say efficiency when Pooh had pronounced it as "a fish in the sea", Christopher turns around only to suddenly discover that Pooh has disappeared.
    • The World War II scenes, brief as they are, brings some serious Mood Whiplash to a franchise such as Winnie the Pooh.
  • Older Than They Think:
    • Given that the Disney cartoons typically set things in some type of American-type setting, many people would find it surprising that this movie is on the London area. This is a callback to how the original books are also set in the London area, but adaptation displacement is at play since the Pooh animated projects are more well known than the books they're based on.
    • This isn't the first time we see Pooh and friends in live-action form with a real-world setting. Back in 2011, to promote the release of Winnie-the-Pooh, Disney made a series of 7 shorts called A Winnie The Pooh Smackerel, which features Pooh and friends doing cute and fun things, and before that, there was The Book of Pooh, which depicts the Hundred Acre Wood gang as Jim Henson-esque puppets.
  • Periphery Demographic: Played with - the primary demographic of this film appears to be the inverse of the original Disney shorts. Plenty of people have grown up with Winnie-the-Pooh and still hold affection for him, which is reflected by having the story take place during Christopher Robin's adulthood.
  • They Changed It, Now It Sucks!:
    • The fact that, outside of Pooh and Tigger, all of the voice actors for the Pooh characters were replaced for this film, has been met with a decidedly mixed reaction. Special mention goes to Eeyore, who a lot of fans wanted Peter Cullen to reprise the role (even though Brad Garrett has voiced Eeyore before, he's not the voice for him, especially since Peter reprised the role for the crossover with Doc McStuffins over a year and a half prior to the movie). A lot of fans were also shocked and extremely disappointed when Nick Mohammed was chosen for the role of Piglet instead of Travis Oates (who has kept the role ever since John Fiedler's death from cancer in 2005), stating that Mohammed didn't even come remotely close to a Fiedler impression like Oates' portrayal.
    • There have also been complaints about some of the changes in character design, such as Tigger being a pale yellow-tan as opposed to his trademark bright orange. Piglet's sweater being green instead of pink is mostly getting a pass, being based on his original illustrated appearances rather than the cartoons.
  • They Wasted a Perfectly Good Character: Besides Pooh, Piglet, Tigger, and Eeyore, the other residents of the Hundred Acre Wood don’t get much screen time or focus. Kanga especially feels underutilized given that she's also a parent and could've bonded more with Christopher Robin over it. It doesn't really help that their voice actors in this film: Sophie Okonedo, Peter Capaldi, and Toby Jones are some of the most acclaimed actors from the UK and they're being used for what are essentially glorified cameos.
  • Uncanny Valley:
    • Some people feel CGI Pooh looks... too creepy (his mouth hardly even moves in sync with his lines). May also count as Ugly Cute, though. Especially when compared to Seth MacFarlane's Ted in which the CGI stuffed bear was much more fluent and realistic.
    • Tigger's eye style look can come off as this when looked up close, by virtue of combining some of his animated character's facial characteristics with the eyes of the original Tigger toy.
  • Win the Crowd: A lot of Pooh fans who were skeptical of the idea of this film were won over by the first teaser as well as the fact that Jim Cummings reprises his roles as Pooh and Tigger.
  • The Woobie: Pooh, for much of the movie. After finding that all his friends have disappeared, he seeks out and meets Christopher Robin again after so many years, only to be constantly brushed off by the now fully-grown and over-stressed Christopher who has no patience for his antics. It's hard not to feel a bit bad for him as a result.

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