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Character page for the 2018 film Christopher Robin.

For character tropes not specific to the film, go to Winnie the Pooh.


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Residents of the Hundred Acre Wood

    Winnie the Pooh 

Winnie the Pooh

https://static.tvtropes.org/pmwiki/pub/images/winnie_3.png

Voiced By: Jim Cummings

"It's always a sunny day when Christopher Robin comes to play."

  • Achievement In Ignorance: Most of Pooh's achievements, by his own admission, are the result of either doing nothing at all or just walking in a random direction.
  • Big Eater: Implicitly. He's not seen eating an enormous amount of honey at any particular time, but he frequently gets hungry and his thoughts tend to stray towards food rather often.
    Pooh: This is all very confusing. It may be the hunger.
    Christopher: You've just eaten!
    Pooh: Oh that's right. Maybe I didn't eat enough.
  • Cloudcuckoolander: His talent for Comically Missing the Point is unrivalled, and his mind works in its own special way that often has very little to do with logic or reality. Though quite often his conclusions turns out to be very sound.
    Pooh: I am a bear of very little brain.
    Christopher Robin: I think you're a bear of very great heart.
  • Friend to All Children: Despite being a stuffed animal and having a childlike demeanor, the fact that Roo exists in the movie, indicates that Pooh is technically an adult, so he fits this trope. He demonstrates this when he excitedly asks Christopher Robin if Madeline can come to play with them after first lays eyes on Madeline when Christopher Robin sneaks past the window of the summer cottage in Sussex to get Pooh back to the Hundred Acre Woods without being seen by her or Evelyn. By the end of the movie, Pooh and Madeline form a strong friendship.
  • Nice Guy: Even when Christopher Robin never comes back to Hundred Acre Woods for nearly thirty years, Pooh never holds a grudge towards him and is overjoyed to finally reunite with him and willing to help his family as well. When he, as per usual, describes himself as a Bear of Very Little Brain, Christopher tells him that he is in fact a Bear with a Very Big Heart.
  • Old Friend: Pooh was Christopher's friend during his childhood, and comes back at him in adulthood.
  • Simple-Minded Wisdom: Despite being a self-proclaimed "Bear of Very Little Brain", he ends up dispensing a fair bit of unconventional wisdom.
    "Sometimes doing nothing leads to the very best something."

    Piglet 

Piglet

https://static.tvtropes.org/pmwiki/pub/images/piglet_2.png

Voiced By: Nick Mohammed

  • Adaptation Dye-Job: Piglet's sweater is green instead of his usual pink, which reflects the original illustrations rather than the Disney animated adaptations.
  • Lovable Coward: He may need a little encouragement, but Piglet does go along with Pooh and the others to help Christopher Robin in London.
  • Nervous Wreck: Piglet tends to be fearful about pretty much everything new or potentially dangerous.
  • Not So Above It All: During the farewell party, Tigger and Roo frantically scarf into Christopher Robin's cake like rabid animals. Piglet politely takes a slice, and proceeds to do the exact same with it.

    Tigger 

Tigger

https://static.tvtropes.org/pmwiki/pub/images/tigger.png

Voiced By: Jim Cummings

  • Dumbass Has a Point: Swapping Christopher's paperwork for Hundred 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.
  • "I Am" Song: The Wonderful Thing About Tiggers which he sings when he, Pooh, Piglet and Eeyore meet Madeline and she asks "What's a Tigger?"
  • Keet: Tigger is the most hyperactive member of the group.
  • The Pollyanna: Though he might lose his nerve if he thinks Heffalumps are lurking, on the whole Tigger is a perpetual optimist who is absolutely certain that everything is going to work out no matter what.
  • Nice Job Breaking It, Hero: He was the one that took out Christopher's important papers, which means he, Pooh, Piglet, and Eeyore have to travel to London to give them back to him.

    Eeyore 

Eeyore

https://static.tvtropes.org/pmwiki/pub/images/eeeyore.png

Voiced By: Brad Garrett

"I don't remember being cheery."

A stuffed donkey who stands out with his rather jaded, gloomy personality, he shares many of the same tropes as his animated self.


  • Ascended Extra: 'Extra' is extreme, but Eeyore's appearances prior to this film were growing more and more sparse, here he's one of the Hundred Acre Wood residents to leave the forest in search of Christopher Robin and as a result he gets a larger share of the spotlight.
  • Beware the Nice Ones: Eeyore wouldn't hurt a fly, so when he gives you the evil glare, you know you've crossed a line.
  • The Cynic: Par for the course with gloomy old Eeyore.
    *playing 'Say What You See'* "Disgrace, shame, humiliation..."
  • Deadpan Snarker: His cynicism also leads to a lot of dry remarks.
    (being held under Christopher's arm) "Thank you for kidnapping me."
  • Death Glare: He shoots Giles Winslow with an unimpressed stare right before Christopher Robin takes them back to the countryside, and it's so emotive that Giles realizes that Eeyore is more than just a stuffed animal. Of course no one believes him when he tries to point it out.
  • The Eeyore: The trope originator himself, perpetually gloomy, deadpan and pessimistic. He's often played up as a contrast to The Pollyanna that is Tigger.
  • "Eureka!" Moment: Has one when he realizes that the "heffalump" who kidnapped him is actually Christopher Robin as an adult, and it's so powerful his normally droopy eyes go wide and he smiles.
  • Not So Stoic: His flat disinterest breaks a handful of times in the film, mostly after he leaves the Wood to find Christopher Robin.
    *in a trunk that's being dragged through the streets by a rope that tethers it to the moving truck*: "I wanna go home!"
    *in the grasp of an adult Christopher Robin, who Eeyore believes is a heffalump as everyone is arguing that matter*: "Help me."
  • Only Sane Man: Quick to point out when his fellows are acting foolish, such as when Christopher sets to fight an imaginary Heffalump and when Tigger admits to switching out Christopher's important papers for mementos from the forest.
    Tigger: "But he forgot his Important Papers... which might have been a smidge my fault."
    Eeyore: "It was your fault!"
  • The Stoic: Like always, he's not one to give in to emotion easily. It's implied that he's like that because he thinks bad things that happen are inevitable and there's no point in panicking.
    *very, very flatly* "Do we [care that Christopher Robin is leaving]? We do."
  • Talking in Your Sleep: Eeyore mutters "saddle's too tight" in his sleep.
  • When He Smiles: He's just as gloomy and sullen as you remember but when he realizes that who he thought was a Heffalump was in fact Christopher Robin and his old friend was playing again, Eeyore's smile lights up his entire face. Then he starts playing along to convince the others too.
    Eeyore: It's Christopher Robin... he's playing again...

    Rabbit 

Rabbit

Voiced By: Peter Capaldi

  • Adaptation Dye-Job: Rabbit's fur is brown instead of yellow as in the animated movies.
  • Adaptational Nice Guy: Rabbit, while a bit insistent on manners and protocol, is far more humble than his original novel counterpart.
  • Demoted to Extra: Rabbit only appears in a few scenes, contrasting with his usual role as part of the core ensemble in earlier films.
  • Trademark Favorite Food: During a party, Rabbit openly hopes the cake Christopher Robin brought along is a carrot cake.
  • Vitriolic Best Buds: Surprisingly there's more emphasis on him bickering with Owl than Tigger in this film.

    Kanga 

Kanga

Voiced By: Sophie Okonedo

  • Demoted to Extra: She only appears briefly during the Heffalump fight and again at the end when Christopher brings his family to the Hundred Acre Woods, and doesn't join the core cast in the expotition to Lon Don.
  • Mama Bear: When the animals are hiding from what they think is a Heffalump, and Kanga (while not showing signs of aggressiveness) is seen protecting Roo in her pouch.
  • Not So Above It All: Much like the novels and 2011 movie, she maintains her dignified motherly personality, but is more susceptible to the gang's usual suspicions than her Disney counterpart is usually known for, hiding from Christopher Robin with everyone else after they mistake him for a Heffalump.
    Kanga: He's hideous!
    Christopher Robin: Well that's a bit harsh.
  • The Smurfette Principle: As in other incarnations, she is the only female resident in the Hundred Acre Wood.

    Roo 

Roo

Voiced By: Sara Sheen

  • Armor-Piercing Question: He does it unintentionally, but when he asks "Then, why isn't she with you?" after Christopher Robin says "she means the world to me" (referring to his daughter Madeline), it clearly hits Christopher hard.
  • Big Brother Worship: It's not in limelight as much, but Roo's fondness for Tigger and his bouncing is definitely visible.
  • Demoted to Extra: Roo had been a main character for a long duration in the Disney canon beforehand, while here he is back to a supporting role.
  • Not Allowed to Grow Up: Christopher Robin spent approximately thirty years away from the Wood, but Roo looks and acts exactly the same when he returns as an adult. Apparently justified since he's a stuffed toy.

    Owl 

Owl

Voiced By: Toby Jones

  • Demoted to Extra: He doesn't join the expotition, meaning he doesn't get as much screentime as the core cast.
  • Ditzy Genius: While Owl tries to come across as wise, he's often a bit ditzy.

    Heffalumps and Woozels 

  • Adaptational Badass: While they still don't actually exist, the Heffalumps and Woozles are given joy-eating, dream-stealing properties. In the books and cartoons, they just stole honey.
  • Emotion Eater: They feed on grief and sadness.
  • Real After All: Played with. They do appear in Christopher's nightmares and scare his friends, but don't really exist. However, Winslow serves as a counterpart to them in the real world.

Humans

    Christopher Robin 

Christopher Robin

Portrayed By: Ewan McGregor, Orton O'Brien (young) Other Languages

"Sometimes doing nothing leads to the very best something."

Our very own Kid Hero All Grown-Up, Christopher Robin began the film as a young boy saying goodbye to his friends and the Hundred Acre Wood. In the present day, he works as an efficiency manager for Winslow Luggage under a demanding, sleazy boss.


  • Adaptational Angst Upgrade: To the world at large, Christopher Robin is the happy, innocent child who spent his days in the Hundred Acre Wood playing with Pooh and his friends. The film puts him through the wringer by having him shipped off to boarding school, losing his father in World War I, then having him fight in World War II, then being forced to work under a Jerkass of a boss who wants all the staff fired for cost-cutting measures, forcing him to miss out on his planned vacation with his family. It takes Pooh showing up in his life to help him become his old self.
  • Adaptation Name Change: Unlike the real Christopher Robin Milne and his counterpart in the original Pooh stories, "Robin" is Christopher's actual last name here.
  • Audience Surrogate: As an adult, Christopher can reflect on everyone who grew up with Winnie the Pooh.
  • Clothing Reflects Personality: When we first meet Christopher as a child, he is wearing light-colored clothes. The change begins with his trip to boarding school, with a dark uniform, and 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.
  • 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. He was aware that he was going to be a father, as Evelyn is visibly pregnant as she sees him off, but he didn't get to meet his own child until she's already three years old.
  • Dark and Troubled Past: He was sent to an abusive boarding school, then broken by World War II.
  • Defrosting Ice Queen: Gender Flipped. Over the course of the movie, Christopher breaks out of the cold, distant shell he's encased himself in over the years and brings the cheer and imagination of his childhood self back out, with the help of his friends in the Hundred Acre Wood.
  • "Eureka!" Moment: Has a big one when he realizes the best way to save Winslow Luggages is to do nothing after Evelyn comments that "good or bad" all depends on how you look at it, and he turns his graph upside down to look at it a different way. To clarify, he realizes that the key to saving the company isn't drastically reducing its manufacturing costs or laying off workers (which he'd been ordered to do), but increasing its revenue by drastically increasing its target consumers from 'the elite rich' to 'everyone who might want to take a vacation'.
  • Family Man: Subverted, the film has him learning how to be one. He always loved his wife and daughter, but his loveless childhood, and career-driven upbringing make it difficult for him to encourage Madeline's creative side and it's implied his time in war has left him emotionally closed off.
    Evelyn: That's the thing, I haven't seen you smile or laugh in ages.
  • 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, depressed 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.
  • Foil: A clear-cut one to Giles Winslow. While Christopher looks out for his fellow employees and works perhaps a bit too hard, Winslow doesn't care about his subordinates' well-being at all and is content to overwork them while doing nothing of value himself.
  • 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.
  • Jade-Colored Glasses: Growing up did not treat Christopher Robin kindly, nor did service in World War II, nor working under Giles Winslow. He's eventually reduced to a stoic shell of his former self.
  • Jerkass Ball: He's mostly a decent man who came back from the horrific war, compassionate towards his fellow workers at Winslow Luggages and family, but when Pooh reappears in his life once again, the latter's persistent to go back to the Hundred Acre Wood together to help find their friends, mutters about Heffalumps and Woozles which Christopher dismisses it as pure imagination, and worse of all he nearly make Christopher's work papers blow up in the wind after they reach their cherished place, which then his exasperation towards Pooh reaches past his limit causing him to angrily tell him off resulting in Pooh leaving him and Christopher guilty for upsetting him. It takes him falling into a Heffalump trap, passing out from the slight trauma of falling, experiencing a nightmare of Pooh leaving him, reuniting with Eeyore and Piglet, then pretending to defeat a Heffalump to reunite with Tigger, Rabbit, Owl, Kanga, and Roo again to restore not only his smile, but his imagination and his relationship with Pooh.
  • Kid Hero All Grown-Up: Christopher Robin is now over 40 years old (Ewan McGregor is 46) and married.
  • O.O.C. Is Serious Business: A major point of his character is how not himself he is. In comparison to the rest of the Disney canon, Christopher Robin is a brash, overworked, unapologetic workaholic. He has lost his sense of childhood innocence and consistently fails to make time for his family. When he first sees Pooh, he's more shocked and annoyed than anything, and eventually even yells at Pooh in a bout of frustration the franchise has never seen. This juxtaposition wouldn't make sense to a new viewer, but anyone who grew up watching the Disney adaptations (or reading the books) would see just how drastically his personality has shifted. Of course, this isn't a mistake or an accident. Christopher Robin regaining his childhood wonder and sense of family is the focal point of the entire film.
  • Poor Communication Kills: Christopher's main problem may not actually be that he works too hard or grew up too fast, but rather that he's forgotten how to properly talk to people. As a child, he was the one who explained things to Pooh and helped make sense of confusing subjects; as an adult he only ever gives half-explanations and gets exasperated when others don't immediately get what he means. While this is occasionally played for laughs with Pooh and friends Comically Missing the Point, it also causes a lot of trouble and unnecessary heartache in his life. He could have told Evelyn and Madeline that people's jobs were on the line and that was why he had to spend the weekend working; instead he just half-heartedly repeats Mr Winslow's words about dreams not being free and nothing coming from nothing. The result is that he accidentally makes himself feel colder and more work-obsessed than he really is and causes tensions and hurt feelings that could have been avoided if he'd just explained his situation properly.
  • 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. He does another earlier when reuniting with Pooh and thinks he's hallucinating.
  • Shell-Shocked Veteran: He was completely emotionally destroyed by his service in World War II.
  • These Hands Have Killed: In response to Pooh's warm declaration that "You are Christopher Robin", the latter sadly chokes out "I'm not a hero, Pooh, 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!"
  • Took a Level in Idealism: He may have to live with traumatic memories of World War II but Christopher finally becomes more optimistic, a bit childish, happy and imaginative thanks to his reunion with Pooh and everyone followed by him helping his fellow employees at Winslow Luggages with Pooh and his friend's help, amending his distant relationship with his family and introducing them to his Hundred Acre Wood friends at the end.
  • Took a Level in Kindness: Christopher is still a good man, just broken by abuse and war, driven to cynicism and overwork. Pooh and the others from Hundred Acre Woods have to remind him what happiness is, making him a kinder man.
  • Trauma Conga Line: Christopher Robin gets sent to a Boarding School of Horrors where his imagination is beaten out of him, his father dies while he's away from home, he meets his wife, and then gets sent away to fight in WWII and misses the first three years of his daughter's life, only to return to a job where he has to cut corners on behalf of a Jerkass woozle of a boss. By the time we properly meet him, Christopher is a walking wound.
  • Used to Be a Sweet Kid: Our Christopher used to be an imaginative, cheerful and innocent kid. But after he left the Hundred Acre Wood for boarding school, life was really harsh on him as he slowly forgot Pooh and his friends, his father died during World War I, when he reaches adulthood and had a family with a wife and daughter, he had to enlist in the British Army during World War II which traumatized him and slightly distanced from his family due to work. After Pooh and his friends arrive to help him, he gets better.
  • 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.

    Evelyn Robin 

Evelyn Robin

Portrayed By: Hayley Atwell

  • Brainy Brunette: She has both brains and dark colored hair.
  • No Historical Figures Were Harmed: She's based on Christopher Robin's real life wife, Lesley.
  • Only Sane Woman: Knows from the get-go that Christopher focusing only on work is not healthy and he needs to spend more time with her and their daughter. Subverted later on, when it seems that her husband has cracked under the stress of work when he's trying to tell her about Pooh and the others, but it turns out he's telling the truth.

    Madeline Robin 

Madeline Robin

Portrayed By: Bronte Carmichael

  • Book Worm: Even though it could trace back to Madeline wanting to please Christopher the fact that she was able to breeze through all her summer reading so easily as backed up by both Madeline and her mom indicate that Madeline likes reading enough to be so good at it. One of her favorites is Treasure Island.
  • Child Prodigy: While the movie doesn't advertise it as much as say Matilda, Madeline has shown to be remarkably intelligent, quick-thinking and attentive for a girl her age. As stated above she read through all her reading assignments with seemingly no difficulty, she could quickly figure out that a "woozle" was actually just Pooh Bear mispronouncing the name of Christopher Robin's boss "Winslow", she could find her way to the train station from the cottage all by herself, she was responsible enough to leave her mom a note before leaving, she knew which train to get on in a crowded station, and finally Madeline knew the address of her father's workplace well enough to tell a cab driver despite being in a bit of a frenzy. Smart cookie, indeed.
  • Generation Xerox: In many ways, she's quite like Christopher's childhood self. Naturally, she gets along with the Hundred Acre Wood residents very quickly. She also has long hair like her mother, and it's partway between Evelyn's brunette and Christopher's redhead.
  • Nice Girl: A defining trait of hers. She goes out of her way to return her father's paperwork to him. Also, she is kind to Pooh and his friends.
  • No Historical Figures Were Harmed: She's based on Christopher Robin's real life daughter, Clare.
  • "Well Done, Daughter!" Girl: As Evelyn says, Madeline would do anything to please her father. It's Deconstructed though, since Christopher starts out as so career-oriented he's apparently pushed his daughter into focusing on work so much that she doesn't really know how to just go outside and play.
  • You Can Talk?: Madeline Robin's general reaction to Pooh and the others at first. "Y-You're talking!"

    Giles Winslow Jr. 

Giles Winslow Jr.

Portrayed By: Mark Gatiss

"Dreams don't come for free. Nothing comes from nothing."

  • Animal Motifs: Woozles. His actions and attitude suck the sweetness out of his workers' lives for his own benefit, just as a woozle steals honey for himself.
  • Bad Boss: He's more of a slave driver than a boss, given the way he overworks his employees to the point of not even giving them vacation time, and is determined to fire a significant fraction of the staff. How significant? Robin and his staff have been struggling mightily to pinch pennies and have managed to cut costs by 3%. Woozle demands twenty.
  • Big Bad: The closest thing to an antagonist in the film.
  • Corrupt Corporate Executive: Downplayed. The extent of his corruption seems to be in finding ways to do as little work as possible so he can goof off on company time while still looking good for the CEO (his father). These include: Foisting his tasks off on underlings even when it interferes with their personal lives, never examining a problem after he's considered the quickest most short-term solution, golfing on company time while his underlings work their butts off, and attempting to take half-credit for his underlings' work. At no point is he shown doing anything outright illegal. In short, while he's not someone you'd want as your boss, he's also well towards the shallow end of corruption.
  • Evil Counterpart: "Evil" is probably a bit strong, but he's definitely Christopher Robin's darker foil, being rather lazy, dismissive and flippant towards the prospect of the luggage division being shut down and all the employees losing their jobs. This contrasts with Christopher himself who, even at his less sympathetic overall, still genuinely cares about his fellow employees keeping their jobs and making his family happy (even if he's going about it wrong).
  • Hate Sink: He's smug, demanding, and lazy, making him easy to root against. Cementing his status as one is the nit is revealed 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.
  • Hypocrite: Makes Christopher Robin cancel a weekend vacation with his family to work tirelessly on a way to increase profit, all while he himself goes golfing on a weekend vacation and takes credit for his overworked employee's hard work.
  • Jerkass: He's definitely a lazy sleaze of a person.
  • Jerkass Has a Point: Subverted. He seems to make a good point with his "sink or swim" speech to Christopher Robin, pointing out how important hard work is. However, we later see that he doesn't believe a word of it and spent his time golfing instead of doing his part to help.
  • Laser-Guided Karma: After Christopher Robin suggests they cut prices and sell to more than just the rich and let their employees go on vacation, Winslow Jr. dismisses the idea. His father, on the other hand, commends the idea and goes through with it. Not to mention, it gets quickly revealed that he didn't contribute to the plan at all, instead spent the entire weekend golfing, getting humiliated by the same father he thought he'd be able to impress easily.
  • 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.
  • Rich Bitch: Implied, given the way he dismisses Christopher Robin's idea of making their luggage more affordable to the public, listing off things that the common folk like as if they were subhuman, even calling them the very insulting term of "hoi polloi". It's so disgusting that even before his father calls him out, there's quick cut to an elderly board member who shoots an insulted look at him. Of course, it fits with the fact that he doesn't seem to give a damn about, and even looks down on, Christopher and the workers having lives they need to prioritize over work.
    Giles: (with a very snobbish expression and tone) Oh great! Our lovely beaches rammed with hoi polloi, with their gramophones and bottles of cider.
  • Seven Deadly Sins: He embodies the sin of sloth in most aspects of his lazy nature, but also has pride when it comes to his ego of being the CEO's son.

    Winslow Sr. 

Winslow Sr.

Portrayed By: Oliver Ford Davies

  • Benevolent Boss: He comes across as rather stuffy and intimidating, but when given a good idea to raise profits rather than cutting costs and being convinced of its merits, he's willing to go along with it.
  • The Dreaded: His appearance at the board meeting is what prompts a lot of the stress and drama of the film, as he holds the company in his power and is capable of closing Christopher's department and firing all the staff who work there. Subverted however, since when he shows up he's revealed to be a quite reasonable and fair-minded man, if a bit stuffy and pompous and rather withering to his son (not without reason, mind you).
  • Reasonable Authority Figure: 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). However, 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.
  • Small Role, Big Impact: He only appears in the ending scene, but the meeting with him drives the plot of the film, with Christopher Robin struggling to come up with a solution to satisfy him without neglecting his family in the process.

    Cecil Hungerford 

Cecil Hungerford

Portrayed By: Paul Chahidi

  • Cranky Neighbor: Inverted. He's a nice guy who just wants to be Christopher's friend, and enjoy a good game of gin rummy. He's only an irritant because Christopher is all work and no play, and he's only a problem to the plot because Christopher doesn't dare let him see Pooh.
  • Kindhearted Cat Lover: Appears to be quite friendly and openly admits to loving cats.
  • Nice Guy: He's friendly and tries to get Christopher Robin to play gin rummy with him.
  • Nosy Neighbor: Unfortunately, some of his attempts to get Christopher Robin to play gin rummy appear to annoy him.

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