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"Perhaps it's our turn to save Christopher."
Winnie-the-Pooh
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Christopher Robin is a 2018 Walt Disney Pictures fantasy film directed by Marc Forster, with a screenplay written by Tom McCarthy, Alex Ross Perry, and Allison Schroeder. It was released on August 3, 2018.

The story is based on A. A. Milne's Winnie-the-Pooh, and is the franchise's first live action film adaptation. Christopher Robin, the human friend of Winnie-the-Pooh, is now all grown up, and he has lost all sense of imagination. It's up to Pooh and his friends from the Hundred Acre Wood to re-enter Christopher's life and help him find it again.

Previews: Teaser. Trailer.

Not to be confused with the 2017 film Goodbye Christopher Robin, which is a biopic about A. A. Milne and his Real Life son Christopher Robin, who inspired the character.

    Cast 
The film boasts an All-Star Cast, replacing the usual voices of Christopher Robin's childhood friends with the notable exceptions of Jim Cummings and Brad Garrettnote  as Pooh, Tigger and Eeyore with some of the UK's most talented actors.

The human cast includes:

The residents of the Hundred Acre Wood are performed by:

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Christopher Robin provides examples of:

  • Absentee Actor: Gopher is notably absent in this film, and the only resident of the Hundred Acre Woods not seen or mentioned; he hasn't been seen in the franchise since 2006's Kingdom Hearts II. This might be due to gophers not being native to Britain and the character not being present in the original books.
  • Adaptation Dye-Job: Piglet's sweater is green instead of pink and Rabbit's fur is brown instead of yellow or green, either to reflect the realism of the film or to make them look closer to the way they did in the illustrations of A. A. Milne's novels.
  • Adaptational Badass: While not real, the Heffalumps and Woozles are given joy-eating, dream-stealing properties. In the books and cartoons, they just stole honey.
  • Adult Fear:
    • Your day job is conflicting with your family time, and then you have to spend your weekend working on layoffs. It gets to the point that Evelyn all but leaves Christopher when he briefly appears at the cottage only to leave again.
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    • Both Evelyn and Christopher get it when Madeline ventures off to London by herself, with Pooh, Piglet, Tigger, and Eeyore, and are frantically searching the city for her.
    • Christopher Robin worries that being late for his meeting and not having come up with a solution to reducing expenses means that his job is very much in danger, which would leave him without a means to provide for his wife and daughter. He's right. His boss's reaction when it looks like Christopher doesn't have a solution ready is to fire the entire department. Fortunately, Christopher finds a new solution in the nick of time that impresses the CEO enough that he pulls rank.
  • Arc Words: Two contrasting phrases are brought up throughout the film and recur frequently: "Nothing comes from nothing" and "Doing nothing often leads to the very best kind of something."
  • Ascended Fridge Horror: This film is based on the idea of Christopher Robin growing up and its impact on Pooh and his friends, a concept that was only hinted at in previous works.
  • Avoid the Dreaded G Rating: This is the first Pooh project to ever get a PG rating despite previous movies getting a G rating and the cartoons being rated TV-Y. Then again, this isn't the only time it's happened to a lighthearted franchise like this. The PG rating presumably comes from a 10 second clip showing Christopher Robin fighting in a battle in WWII, because there's nothing else that would definitely push it into PG territory.
    • Averted in Australia, where the film was rated G for "Very Mild Themes."
  • Big Bad: Winslow, Jr., Christopher Robin’s overbearing and sleazy boss, is the closest thing to a main antagonist that the film has, since it's Christopher’s desire to save his coworkers’ jobs from him that drives much of the plot, and Pooh and Madeline’s “expotition” in the city in the third act.
  • Book-Ends: The film begins with Christopher Robin entering the Hundred Acre Wood through his tree and sitting with Pooh on a log staring out into the sunset. The same thing happens at the end of the film, but this time, Madeline enters through the tree first, followed by her father, and later her mother, and Christopher and Pooh stare at the sunset once again.
  • Brick Joke: During the search for their daughter, Christopher introduces Evelyn to the gang as "Evelyn, my wife." Later, Eeyore continues to call her "Evelyn my wife."
  • Busby Berkeley Number: "Busy Doing Nothing", which appears halfway through the end credits, featuring home movie-style footage of the Winslow employees vacationing at the beach and dancing, with Richard Sherman playing the piano.
  • The Cameo: During the end credits, while everyone is enjoying their beach holiday, Disney Legend Richard M. Sherman appears as a dapper piano player singing the original song, "Busy Doing Nothing".
  • Cassandra Truth: When Christopher finds all his friends hiding, they initially don't believe he's himself and deem him a Heffalump in disguise. Once he fakes a fight with one, they recognize him as their friend.
  • Chekhov's Gun: At the farewell party, Piglet gives Christopher Robin a sack full of haycorns to remind him of the Hundred Acre Wood. Later, when Christopher is married to Evelyn and has a daughter, Madeline, she discovers the sack full of haycorns and a drawing he made, with Madeline later recognizing Pooh from her father's earlier drawings.
  • Clothing Reflects Personality: When we first meet Christopher as a child, he is wearing light-colored clothes; after the Time Skip to him as an adult, his wardrobe becomes darker and mostly grey and black, showing he lost his sense of childhood. As the film progresses, his wardrobe becomes progressively lighter and in the final scene, he wears a red sweater vest to symbolize he's once again a child at heart.
  • Continuity Nod:
    • The opening scene is the last chapter of The House at Pooh Corner, previously animated in The Many Adventures of Winnie the Pooh. Pooh mentions that he's good at doing nothing and that he does nothing all day. Christopher Robin, who had begun attending school, asked Pooh to remember him when he grows up, because grown-ups will have to do 'nothing'.
    • When Christopher Robin gets stuck in a gap in a tree, Pooh asks if he just ate honey, a nod to Winnie the Pooh and the Honey Tree, where Pooh got stuck in Rabbit's burrow after eating too much honey.
    • When riding in a taxi around London, Tigger calls his reflection in the window a "preposterous impostor", referencing his first scene in the original film.
    • Christopher Robin discovers that Owl’s treehouse has fallen over “again”, much like it did in Winnie the Pooh and the Blustery Day.
    • The third act involves Pooh and his friends venturing out of the Hundred Acre Wood to save Christopher from what they believe to be a monster, just like in Pooh's Grand Adventure. This time, though, Pooh misinterprets it because Christopher Robin directly told him he would be eaten by a Woozle if he lost his work papers (a simplified way of telling Pooh if he lost the papers, he loses his job thanks to his boss Winslow), meaning that Pooh takes Owl’s place of mistakenly sending them on an adventure.
  • Corrupt Corporate Executive: Giles Winslow, Jr. wants to cut down company cost by 20% and he suggests getting rid of the entire Efficiency Department. While it is not entirely unreasonable for a business to do so, it's later revealed that Winslow, Jr. was playing golf all weekend instead of helping Christopher balance out the budget and present it before the company board. Once this is revealed, everyone present calls him out.
  • Covering for the Noise: Often when Pooh spoke to a person besides Christopher, Christopher would have to cover it up by speaking quickly over him. However, when his annoying neighbor spotted him carrying Pooh in his coat, he had to pretend Pooh was a sick cat. When Pooh started talking, he insisted it was his own voice, just changed to sound like Pooh's.
  • Dad the Veteran: Christopher is this to Madeline, having served in World War II. Just like the real Christopher Robin Milne, who was a sapper in the British Army for the entire duration of the war. Sadder when you realize that Christopher was aware that he was going to be a father, as Evelyn is visibly pregnant as she sees him off, but he doesn't get to meet his own child until she's already three years old.
  • Demoted to Extra: Rabbit, Kanga, Roo, and Owl suffer this, since they are relegated to only a few scenes and do not join the “expotition” into London. Rabbit and Roo are particularly notable, since the former is usually a part of the main cast of Pooh media (though he has been the most likely of the core five to get shafted or left out), and the latter enjoyed a large amount of spotlight in the 2000’s. Kanga in particular only gets a small handful of lines.
  • Deus ex Machina: It's pure luck that of all the windshields of all the cars on the streets of London the one Tigger, Eeyore and Piglet land on is Christopher Robin's.
  • Disappeared Dad: Christopher Robin's father died when his son was at boarding school, forcing young Christopher to become the man of the house at a very young age. Christopher Robin himself is a downplayed example, he was off at war when his daughter Madeline was born and didn’t meet her until she was three years old. In the present day, due to his busy, hectic schedule, Christopher Robin is largely absent from his daughter's life, which is the main conflict of the movie.
  • Disney Acid Sequence: Christopher Robin suffers one when he falls into the Heffalump trap and is knocked out by a falling rock. He has a nightmare of Heffalumps attacking him, and Pooh begging him to come back to him.
  • Downer Beginning: While the opening has the whimsy and fun wordplay of the classic stories as Pooh and friends throw Christopher Robin a party, it's a goodbye party as he's being shipped off to boarding school. It only goes downhill from there, as we see over the credits how he grows up - the school is pretty much militant, he learns of his father's death while there, and is eventually shipped to the front lines of World War II. The only bright spot is him meeting Evelyn (and even that has a sour point to it, as they conceive Madeline only for Christopher to be presumably drafted).
  • Dumbass Has a Point: Swapping Christopher's paperwork for 100 Acre Wood mementos might have been an impulsive decision on Tigger's part, but he isn't exactly wrong about how Christopher's memory of them has real importance.
  • Earn Your Happy Ending: Thanks to Pooh and friends, Christopher Robin is not only able to reconnect with his wife and daughter, but he's able to find away to keep everyone's jobs and call out his boss for making him work the weekend away without contributing anything.
  • Elephant in the Room: After Christopher Robin tells Giles off, Giles tries to dismiss Christopher's behavior as crazy, prompting the elder Winslow's inquiry:
    Giles: Dear lord, he has lost his marbles.
    Old Man Winslow: Has he? Let's address the Heffalump in the room, shall we? What were you doing this weekend, Giles?
    Giles: What, me? I told you I was working.
    [A golf ball comes out of Giles' pocket]
  • Eureka Moment: When Evelyn tells Eeyore "it's all how you look at it", Christopher looks at the one important paper Madeline saved, turns it upside down and comes up with his improvised idea for the budget meeting.
  • Eyes Never Lie: This was how Pooh was able to recognize Christopher Robin.
  • Fisher King: The weather in the Hundred-Acre Wood seems to adjust to reflect Christopher Robin's moods. When he's a child, it's blissful and idyllic. As he grows up, we see it alter to reflect how he feels about the things happening to him (when he learns his father has died, there's snow; when he meets Evelyn, it's pleasant again, and so on), until when he finally returns as a stressed-out and emotionally-distant adult, it's dark, gloomy, overcast and full of shadows. When he finally starts unwinding and enjoying life again, it's bright and cheerful. When he has to leave again, it's a bit overcast to reflect his regret, but otherwise remains pleasant as he takes his lighter mood with him. Finally, when he and his family visit at the end (with the implication that they'll all be visiting more frequently), it's idyllic once again.
  • The Foreign Subtitle: In Brazil, the movie is known as "Christopher Robin - Um Reencontro Inesquecível". (An Unforgettable Reunion)
  • Generation Xerox: Christopher's daughter Madeline turns out to be just as fun-loving and adventurous as her father was when he was her age. It’s why she strikes up an instant friendship with Pooh and friends.
  • The Ghost: A pretty justified case for the unseen Heffalump.
  • Growing Up Sucks: Christopher Robin has a real bad case of this. He has a wife and daughter whom he loves very much, but his demanding boss forces him to come to the office on a weekend and skip out on a planned family getaway, much to his daughter's disappointment. Then he finds out that his boss wants to cut 20% of the workforce and he's to be the hatchet man. Christopher Robin protests saying he promised his workers good jobs, but his boss won't budge.
  • Hate Sink: Winslow Jr. Being a Winnie the Pooh story, the film has no actual villains. Winslow Jr serves the purpose of being a character the audience can root against.
  • Hell Is That Noise: Once Christopher returns to the Hundred Acre Wood; it's covered in dense fog. All the while, nightmarish elephant sounds seem to be chasing him everywhere, as it seems a Heffalump is stalking its prey. Ultimately, it turns out to be Owl's weather-vane scraping against some metal.
  • Honest Corporate Executive: When his boss Giles Winslow, Jr. tells him their company needs to cut their workforce, Christopher Robin protests, reminding him that he promised the workers good jobs. However, Winslow, Sr. is a straighter example of this, embracing Christopher’s solution to the budget crisis and chastising his son for slacking off and forcing Christopher to do all the work.
  • Hope Spot:
    • For Pooh and friends. When Christopher Robin returns to the Hundred Acre Wood, he reunites his gang of beloved old friends, has some fun, and reconciles with Pooh. Sounds perfect, right? Unfortunately, Christopher still goes to return to his life and his work, leaving his friends once again. Pooh is crushed that his best friend is leaving him once again after a short reunion after so many years.
    • Evelyn and Madeline have one when Christopher turns up at the cottage... only to say he can’t stay. They’re both heartbroken.
  • Human-Focused Adaptation: This film focuses on Christopher and his relationship with his family.
  • Hypocritical Humor: When Christopher Robin finds Pooh in a young boy's stroller at the London train station and takes it back from him:
    Christopher Robin: You can't just take a teddy bear from a grown man!
  • In Which a Trope Is Described: In a clever Mythology Gag to how the chapters of the original book were titled, the sequence of Christopher Robin growing up has odd-numbered significant events titled this way.
  • Ironic Echo Cut: During Christopher's "fight" with the "Heffalump":
    Eeyore: But there's nothing there.
    (Cuts to the log)
    Rabbit: Something is clearly there!
  • Kick the Dog: When Christopher nearly loses his work documents, he goes on a rant at Pooh for reentering his life and messing everything up. Pooh meekly apologizes, but Christopher even calls him a “bear of very little brain” with absolutely none of the trademark warmth the saying is known for.
  • Kid Hero All Grown-Up: Christopher Robin is now over 40 years old (Ewan McGregor is 46) and married.
  • Literal-Minded: None other than the silly ol' bear himself. When Christopher sees Pooh and says he must've cracked (gone crazy):
    Pooh: I don't see any cracks. (feeling Christopher's face) A few wrinkles, maybe.
    • And because Christopher introduced his spouse as "This is Evelyn, my wife.", this results in poor old Eeyore thinking that's her actual name, leading to delightful incidents like:
    Eeyore: (after Evelyn serves him a cup of tea) "Thank you, Evelyn My Wife.
  • Logo Joke: The Disney Castle starts as normal, until the end, when it fades into an E.H. Shepard-type illustration.
  • Mama Bear: When Christopher Robin finds the rest of Pooh's friends hiding. Some are clearly frightened at first, and Kanga (while not showing signs of aggressiveness) is seen protecting Roo in her pouch.
  • Market-Based Title: The French title is Jean-Christophe and Winnie. Christopher has always been named "Jean-Christophe" in Disney's French translations for some reason. Winnie the Pooh is very well known, but Christopher's family name is rarely if ever mentioned in the French dubs of the franchise (though the Milne books call him "Christophe Robin").
    • In Japan, the film's title is "Pooh to otona ni natta boku", which translates into something like "Pooh and I Who Has Become An Adult".
  • Meaningful Name: The name Winslow sounds similar to weasel which in turn sounds like Woozle. Winslow, Jr. is a Corrupt Corporate Executive who puts all the work on Christopher Robin while he goes off golfing. This is how Christopher Robin is able to get the point across to Pooh of why he needs his papers (by saying that Winslow Jr. is a Woozle who would eat him if he doesn't have them) and what sparks Pooh and his friends to travel to London with Madeline when they realize that Tigger didn't put those important papers back in his bag.
  • A Minor Kidroduction: The movie starts with young Christopher Robin attending a farewell party with his friends prior to leaving for boarding school. After that, there is a Time Skip years later to him as an adult.
  • Mythology Gag:
    • The opening is mostly a faithful adaptation of the final chapter of The House at Pooh Corner, which was previously adapted both at the end of Many Adventures as well as the ending of Pooh's Grand Adventure. But this time, they included the party for Christopher and Eeyore's feeble attempt at poetry, which is lifted from the book.
    • The Hundred Acre Wood scenes were filmed at Ashdown Forest, the real-life inspiration for the Hundred Acre Wood setting of A. A. Milne's stories illustrated by E.H. Shepard.
    • The outfit young Christopher Robin wears is based on his outfit from the original Shepard illustrations.
    • Piglet wears a green sweater in this film, as he did in the original books and the opening song of the Many Adventures shorts.
    • Christopher Robin finds Eeyore floating belly-up in a river, in just about the exact same pose he had in the same predicament in A Day for Eeyore.
    • A flashback adapts a moment in the Milne books never covered in any of Disney's prior adaptations: the going away party for Christopher Robin that his friends hold for him. His final goodbye to Pooh, on the other hand, did get adapted for both the epilogue of The Many Adventures as well as Pooh's Grand Adventure; the latter also used the "even when I’m a hundred" line.
    • As noted in Non-Standard Character Design, both Rabbit and Owl are portrayed as actual living animals despite the rest of the cast being stuffed animals, just as they were in the original Milne stories. Unlike the stuffed animals the stories were based on, who are now residing in the New York Public Library, Owl and Rabbit were completely imagined, and presumably, were based on the nearby wildlife.
    • This is not the first time Pooh and friends have entered the “real” world and had misadventures; on several occasions in The New Adventures of Winnie the Pooh, the gang would interact with the real world and people besides Christopher Robin. In “Pooh Day Afternoon”, the characters also found themselves having some vehicular mayhem.
    • Pooh's predicament at the start of the film, that he can't find any of his friends, hearkens back to his storyline in Kingdom Hearts, complete with Christopher Robin fulfilling Sora's role in finding them (ironic, as Sora basically replaced Christopher's role in the story).
  • Nepotism: Giles got his job because it's his father's company and he spends most of his time slacking off. By the end, there's a bit of a subversion at the end when his father finds out he spent the weekend golfing and forced Christopher to do all the work and chastises him.
  • Never Trust a Trailer: One of the promos for the film has Pooh surprising a policeman that he can talk. In the film, he is actually speaking to Madeline.
  • Non-Standard Character Design: Rabbit and Owl are portrayed as a real, living rabbit and owl living amongst the stuffed animals. Similarly, Heffalumps in Christopher Robin’s nightmare are portrayed as very realistic looking elephants with no anthropomorphism.
  • Not Allowed to Grow Up: While Pooh, Tigger and Eeyore appear to have aged a bit since they last saw Christopher Robin as a child, Piglet and Roo appear to be two of the few residents of the Hundred Acre Woods that still show no signs of aging after all these years. Even more evident for Rabbit and Owl, who are in fact real animals instead of stuffed toys like the others yet seem the same as ever.
  • Not Even Bothering with the Accent: Nearly all the Pooh cast are voiced by British actors who use their native accents (only the actors who reprise their roles from previous Disney works use their original American portrayals). This example however is a Mythology Gag due to the franchise's British origin.
  • Oh, Crap!: How else would a grown up Christopher Robin react when finding himself unexpectedly reunited with Winnie the Pooh?
  • Old Friend: Pooh was Christopher's friend during his childhood, and comes back at him in adulthood.
  • Promotion to Parent: When Pooh turns up in London and reunites with Christopher Robin, their dynamic becomes something akin to this. While Pooh has been around since Christopher’s childhood, he’s still very naïve and innocent like a child, whereas Christopher is a mature grown man. Thus, Christopher finds himself exasperatedly trying to hide Pooh’s existence from other people, and even chides Pooh for playing a game on a train while he’s trying to work. Nonetheless, the positive part of this trope is very much in play since Christopher immediately becomes protective of Pooh and clearly cares about him deeply even after all these years.
  • Rapid-Fire "No!": By Christopher when he wakes up the following morning after meeting all his friends and realizes he's late for work.
  • Real After All:
    • In this film's continuity, the Hundred Acre Wood is confirmed to be a real, magical place that Christopher Robin enters through a tree outside his childhood home, Narnia style, and its residents are living sapient beings that can enter the real world and interact with other people. This isn't fully established until the toys meet Madeline and cause unintentional chaos throughout London, as in every scene before, it could be rationalized as Christopher Robin's imagination or something real only he could see.
    • Ultimately Subverted with the Heffalumps and Woozles. When alone in the Wood, Christopher begins hearing hellish elephant-like sounds and begins to fear that this trope is in play after all. He ends up discovering that the Heffalump sounds were actually the distorted wailing of Owl's weather vane.
  • Real Is Brown: Unusual for a Disney and Pooh film, all of the colors are very disaturated to emphasize the depressing reality of what it means to grow up and lose your innocence — even Pooh looks worn and depressed. It's a deliberate example of this trope, as the opening of the film has a brighter, more vibrant color palette, as do the Hundred Acre Wood scenes when Christopher reconciles with his old friends.
    • Piglet wears a dark green sweater as he did in the original stories, as opposed to the vibrant pink he's mostly known for in Disney works, and Rabbit's fur is brown like in the original stories instead of the yellow or green colors he's given in the cartoons.
    • Played With for Eeyore, who is clearly baby blue as opposed to his usual gray. While the character is usually plain blue for merchandising, the real Eeyore is on display in the New York Public Library, and is quite definitely gray.
    • Tigger's stripes have faded to almost be a constant brown. Again, he's faded much more than the real Tigger's has.
  • Reality Ensues:
    • Christopher Robin promises that he will not forget about his childhood toys, but the stress and pressure of adulthood catches up to him and, with other things on mind, he does exactly that.
    • The bear from your childhood appears and starts talking? Christopher Robin assumes he has "cracked" from the stress of his job.
    • Now being a grown man, Christopher Robin can't quite fit through the tree entrance to the Hundred Acre Wood that he used as a child.
    • And in a spiritual sense too, having the blood of countless men forever staining his hands in World War II, Christopher may never truly fit in the joy and innocence of the Hundred Acre Wood again.
    • While Pooh's antics are amusing to his friends and the audience, to an overstressed Christopher Robin they are a major annoyance and frustration. After Pooh nearly causes him to lose important work documents, he finally loses his patience as he recovers them and blows up at Pooh.
    • Stuffed toys on someone's windshield, no matter how adorable, will majorly impair that driver's vision.
    • Not everyone will accept an abnormal event such as animate, talking stuffed animals at first sight. Christopher is forced to keep an oblivious Pooh in "nap time" to avoid being caught, Tigger's hyperactivity freaks out a driver and causes him to crash, and even Christopher's own family is initially skeptical and afraid.
    • In a less serious sense, Christopher is frantic when he sees Eeyore being dragged to the edge of the waterfall, but when he jumps in to perform a rescue he's surprised to discover that the water only comes up to his ankles. Then he remembers that he's grown taller while the Wood has stayed the same, and could have just waded in at any time.
  • Reasonable Authority Figure: Old Man Winslow turns out to be this; he's a bit hard-nosed and curt, and isn't particularly impressed with Christopher's abandoning of the meeting (or the fact that his briefcase is full of acorns and an Eeyore tail). But once things settle down a bit he gives Christopher's ideas respectful consideration, shows appropriate disapproval of his son's feckless laziness, and displays a more good-humoured attitude than he initially seemed to possess.
  • "The Reason You Suck" Speech: When Christopher Robin confronts Giles:
    Giles: What the devil is a "Woozle"?
    Christopher Robin: A "woozle" is a slinking little monster who gets everyone else to do his work for him, and hopes that we forget what's important in our lives: our families, our dear friends, the people who love us, the people whom we love. Well, we're here to tell you, I'm here to tell you that we're not afraid of Heffalumps or Woozles anymore, are we?
  • Redemption in the Rain: Christopher lightens up noticeably after being caught in a rain storm while trapped in the Heffalump and Woozle Trap (although being bonked on the head by a stone while trying to climb out probably also helped). Once he's floated to the top (in a notably Christ-like pose), he starts to engage more with the Hundred-Acre Wood and its inhabitants rather than just curtly brushing them off.
  • Ridiculously Cute Critter: While Pooh, Piglet and Roo's cute appearances has been toned down a bit in this film compared to their animation counterparts, they still maintain their friendly appearance even in live-action form.
  • Role Reprisal:
    • Most of the Winnie-the-Pooh voice actors of previous Disney works have been replaced, though Jim Cummings returns as Pooh himself and Tigger (although it was originally planned that Chris O'Dowd would voice the latter). Brad Garrett also reprises Eeyore, having provided his voice in Disney's Animated Storybook: Winnie the Pooh and the Honey Tree.
    • In the European Spanish dub, all the toys and animals' voice actors (except Roo) reprised their roles. Even Tony Canal, who was semi-retired, returned as Pooh.
    • The same goes in the Latin American Spanish dub, when the voices of all the dolls and animal characters reprise their roles, excluding Eeyore and Roo.
    • In the Japanese dub, all the voice actors from the animal and plush characters reprise their roles, except Pooh.
    • Tigger, Rabbit, Eeyore, Piglet, and Kanga's German voice actors returned.
  • Running Gag: Whenever the human characters are carrying the animal characters through London, they will at some point have to interact with someone else (a train ticket collector, a salesman, a police officer, etc.). When they finish, the animal character will politely repeat the human character's thanks to the person they were interacting with.
    • Cecil asks Christopher Robin if he has time for a game of gin rummy, with Christopher politely declining.
  • Shell-Shocked Veteran: Among the experiences that have sapped away Christopher Robin's childhood innocence are his days as a soldier in World War II.
  • Shout-Out: Rabbit states to his friends that Heffalumps can't see them if they don't move.
  • Shout-Out to Shakespeare: The recurring "Nothing comes from nothing" line is a reference to King Lear, where the titular king asks Cordelia what she can say to surpass her sisters' eloquent speeches, she answers "Nothing", which prompts Lear to respond with "Nothing will come of nothing", which is echoed by Lear's fool a few scenes later:
    Kent: This is nothing, fool.
    Fool: Then 'tis like the breath of an unfeed lawyer: you gave me nothing for it. Can you make no use of nothing, nuncle?
    Lear: Why, no, boy. Nothing can be made out of nothing.
  • Sliding Scale of Idealism vs. Cynicism: The film starts idealistically in Christopher's childhood, before becoming more cynical as Christopher grows up and his life spirals out of control. However, after Christopher rescues his friends, the film slowly climbs back up the scale to land on a very idealistic ending.
  • Something Completely Different: Unlike Disney's previous Pooh movies, this one is live-action, is largely set outside of the Hundred Acre Wood, and features Christopher Robin as a grown adult rather than a child. It's also the first Pooh project to get a PG rating as opposed to the G rating of previous movies, and the TV-Y rating of the cartoons.
  • Something Only They Would Say: Christopher deduces that Madeline is not alone based on the word "expotition" in her note.
  • Something They Would Never Say: The other inhabitants of the Hundred-Acre Wood initially refuse to believe Christopher isn't a Heffalump because he claims that monsters don't exist, which is something the Christopher Robin they remember would never say. Christopher takes this on board and convinces them of who he is by pretending to defeat a Heffalump in combat instead of dismissing its existence.
  • 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.
  • Stealth Pun: When slammed onto the car windshield, Eeyore deadpans, "My bum hurts." Another word for bum is ass, and ass is also an old-fashioned word for donkey. So Eeyore could've also meant, "I hurt all over."
  • Storybook Opening: As a nod to the original featurettes, as well as the books that inspired it, the opening takes place within the pages of the original Milne books, complete with some reproductions of Shepherd's illustrations. Some liberties are taken however. For example, one illustration depicts Christopher and his friends making a "Heffalump and Woozle Trap", but heffalumps and woozles originally appeared in separate stories, never together.
  • The Stinger: During the end credits, an old-fashioned film plays showing the Winslow employees (and Christopher's neighbor) on a beach and singing about doing nothing. The last scene also features Pooh, Piglet, Tigger and Eeyore sitting in beach chairs and wearing sunglasses, and Richard Sherman as a singing piano player.
  • Talking in Your Sleep: Eeyore mutters "saddle's too tight" in his sleep.
  • Tempting Fate: In the prologue depicting Christopher's final afternoon in the Hundred Acre Wood, Pooh asks what he'll do if Christopher forgets him. The boy responds that he'll never forget Pooh, painfully unaware that life and growing up will indeed cause him to forget his childhood friends.
  • Theme Tune Cameo: The iconic song "Winnie the Pooh" is used a few times during the film, the first time being when Pooh wakes up in his home. Pooh also sings "Up, Down, Touch the Ground", and Tigger sings "The Wonderful Thing About Tiggers".
  • These Hands Have Killed: In response to Pooh's warm declaration that "You are Christopher Robin.", our hero sadly chokes out "No, I'm no longer the same person I was, I'm lost." and bitterly weeps like a child as he holds tight onto his old friend, implied to be partially out of having lost another chunk of his innocence in World War II.
  • This Cannot Be!: Christopher Robin's initial reaction to Pooh appearing in his world is "This can't be happening!"
  • Trademark Favorite Food: Pooh's unending quest for honey is actually what drives him to enter the real world in search of Christopher Robin. Piglet's love of haycorns also plays a small role once Christopher Robin returns to the Hundred Acre Woods.
  • Vitriolic Best Buds:
    • The growing difference in maturity and intellect has taken it's toll between Pooh and Christopher Robin, with the latter frequently getting frustrated with the former's childishness. It soon becomes clear he loves his silly old bear as much as before however.
    • Expectedly Rabbit is a bit prickly tempered with the group. Less expectedly, his grievances tend to be less with Pooh or Tigger like usual and more with Owl (who has bickered with Rabbit in earlier works but far less often).
  • Vocal Evolution: Pooh's and Tigger's voices have clearly aged after all these years.
  • War Is Hell: Christopher Robin's time during World War II is an unpleasant experience. Being away from his family (and the birth of his daughter) for three years is bad enough, but Christopher's last remaining innocence is robbed by the constant barrage of gunfire, screams, explosions and dying men in the cold winter.
  • Watching the Sunset: Christopher and Pooh do this three times throughout the film in their usual special spot.
  • When You Coming Home, Dad?: Christopher is called into an emergency weekend meeting and forced to skip an outing with his wife and daughter, much to his daughter's disappointment. When Pooh Bear comes to him for help, Christopher Robin realizes how important his family is to him and decides to go join them at the cottage.
  • You Can Talk?: Madeline Robin's general reaction to Pooh and the others at first. "Y-You're talking!"
  • Your Mind Makes It Real: The Hundred Acre Wood becomes gloomy and morose when Christopher returns to it, and doesn’t brighten up until he begins to have fun and reunite his old friends.

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