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  • Adorkable: Madeline has her moments, such as when she tied the red balloon to her racket and pretended she was playing at Wimbledon.
  • Aluminum Christmas Trees: Christopher's solution of paying the employees more and giving them vacation days models Henry Ford's decision to pay his workers well enough that they could buy the cars they were making. It's good marketing! And for Christopher, it's an opportunity to be kind.
  • Awesome Music: One TV spot uses the classic Winnie the Pooh theme as an epic orchestral piece.
  • Catharsis Factor: When Christopher Robin gives Winslow Jr. a family-friendly "Reason You Suck" Speech.
  • Common Knowledge: Due to it being a live-action film based on an animated Disney work, the film is often grouped alongside the other Disney Live-Action Remakes, despite the fact that the film isn't a remake of any existing Pooh story, but an original story that acts as a distant sequel to the animated Winnie the Pooh films
  • 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 remarks 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 the humans (bar dedicated fans of Ewan McGregor or 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. (He ultimately would do so a few years later in a miniseries.)
    • Also, turning Christopher Robin's reunion with Pooh into the "Hello there" meme.
  • 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.
  • 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 (2011), 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 and even earlier then that, was Welcome to Pooh Corner, which depicted Pooh and friends as costumed characters.
    • This isn't the first time Pooh and friends have interacted with Christopher Robin's world as opposed to the hundred acre woods as they would occasionally do so in The New Adventures of Winnie the Pooh prior.
  • Spiritual Successor:
    • To Hook, a story about a hero who once explored a fantastical world as a young boy, then decided to leave it and grow up in the normal world while missing out on his kids' childhoods. Said hero is pushed to recover his once-vivid imagination to overcome obstacles. Moreover, Christopher Robin is a movie sequel to a beloved classic work of children literature.
    • The same could be said for Return to Oz or Tim Burton’s Alice in Wonderland (2010), which sees the Hundred Acre Wood turned into a dark, bleak place compared to its original glory.
    • The film can also be seen as the true successor to Pooh's Grand Adventure: The Search for Christopher Robin. Both films contend with the concept of Christopher Robin growing up and its effect on his childhood friends he has to leave behind, but whereas Pooh's Grand Adventure mostly focused on whether Pooh and friends would be able to live their lives without Christopher and their immediate reaction to the prospects of it, this film shows the long-term consequences of the inevitable head-on.
  • 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.
  • Unintentional Uncanny Valley: Some people feel CGI Pooh looks... too creepy (his mouth hardly even moves in sync with his lines). May also count as Creepy Cute, though. Especially when compared to Seth MacFarlane's Ted in which the CGI stuffed bear was much more fluent and realistic.
  • Unintentionally Sympathetic: Christopher got this reaction from some audiences and critics — while he's certainly not meant to be unsympathetic, the film treats his situation as a standard When You Coming Home, Dad? plot a la Hook and boils things down to Christopher simply needing to rediscover his childhood. The issue is that Christopher isn't simply overworking; he's effectively been saddled with protecting as many employees' jobs as possible while decreasing expenditures, meaning if he neglects his duties, many innocent people will lose their entire livelihoods. The fact that the film doesn't seem to recognize the urgency of this means you might find yourself taking Christopher's side against Evelyn and Pooh more than the film intends. Then there's the implication of Christopher's PTSD from the war which distanced him from his family and is probably keeping him buried in work.
  • 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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