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  • Many skeptics found themselves won over upon this simple line of dialogue appearing in the trailer, which perfectly encapsulates the interesting relationship with logic that Pooh has:
    Pooh: People say that nothing is impossible. But I do nothing every day.
  • "It's not stress. It's Pooh." Guess who? The first two do not count.
  • Tigger thinks his reflection in a car window is a "preposterous impostor", with Jim Cummings having a ball with his lisp on those two words.
  • Christopher gets stuck in the entrance to the Wood, to which Pooh naturally figures he's had too much honey.
  • Christopher trying to hide Pooh from his neighbor by claiming that he's hiding a cat under his jacket. When that proves to not be enough, he claims that it's a diseased cat. That bites. And needs rehabilitation. Said neighbor buys his god-awful lying.
  • Pooh gets covered in honey and then touches Christopher Robin's face (which covers Christopher in said honey) and then goes wandering about Christopher Robin's house, his feet leaving a trail of honey on the floor as Christopher frantically tries to wash them off. Eventually, Pooh steps on a carpet, getting his feet stuck to it. Talk about a sticky situation.
  • Pooh mistakes a shelf for a ladder and tries to climb it, breaking it out of the wall and spilling the contents.
    Pooh: Your ladder is broken.
    Christopher: That's not a ladder! That was a shelf!
    Pooh: Well, that explains why it was no good for climbing.
    • Even funnier, this has a Disaster Dominoes effect when a coffee can on the shelf rolls across to the other shelf and causes it to collapse as well.
  • Pooh greets a man walking next to Christopher. The man is understandably stunned and ends up walking right into the lamppost in front of him. Both Christopher Robin and Pooh have an "Oh, Crap!" look on their faces.
    • Shortly thereafter, a woman catches Christopher Robin talking to Pooh inside a phone booth and gives a look of absolute confusion. This later becomes a Brick Joke when Christopher and Pooh are on the train, the very same woman attempts to enter their compartment and just backs away slowly.
  • Christopher loses Pooh at the train station and finds him taken by a small child in a stroller. Christopher soon pulls Pooh away from the boy in front of his mother, looking like a crazy person.
    Christopher: You don't just take a teddy bear from a grown man!
  • Pooh playing "Say What You See" on the train while Christopher's trying to work, which naturally starts getting on his nerves. Christopher asks Pooh to play a little quieter, and Pooh obliges by switching to "Stage-Whisper What You See." In response, Christopher gets the expression of a man who's just thoroughly done.
  • A woman walks opens the door to the compartment Christopher and Pooh are sharing and Christopher, desperate, asks for some space because "It's [Beat] his naptime." The woman looks at Pooh, playing naptime, and the grown man alone in a compartment with a teddy bear playing naptime understandably fucks the fuck out of there.
  • Christopher rescuing Eeyore from the waterfall. He takes off his jacket, holds his breath, and prepares to swim for it... and promptly discovers that the water only goes up to his ankles.
    Christopher: Oh yes, of course. I've grown up, haven't I?
    • Just before that, watching Christopher Robin hurriedly gesturing for Eeyore to try and swim.
    Christopher: Swim, swim, swim!
    • To top it off, the big, scary waterfall Eeyore was drifting toward? Its the size of a step on a staircase.
    • Eeyore first seeing Christopher Robin and mistaking him for a Heffalump.
    Eeyore: (as Christopher smiles at him) Just my luck. A Heffalump, leering at his lunch.
  • Eeyore gets his head stuck in a bucket, saying it's "Just an average Windsday morning."
  • Christopher's sheer casualness when remarking on Owl's house blown down again.
  • When Christopher Robin shows that the screeching sound is just Owl's weather vane, Eeyore grumbles "Oh, great. It has a weapon."
  • When Madeline first meets Pooh and his friends:
    Madeline: You're talking!
    Pooh: No, I'm not talking... Well, I am now, I suppose.
    • After encountering Pooh, Eeyore and Piglet, Madeline is then introduced to Tigger. She asks him "What's a Tigger?".
    • Tigger then proceeds to burst into his famous song much to Madeline's absolute bewilderment (the novel instead has her happily clapping and laughing). Apparently, it's a normal (and frequent) thing he does.
    • The same scene also has this, as they're explaining to Madeline what's going on...
    Tigger: But he forgot his important papers! Which might've been a smidge my fault...
    Eeyore: (dryly) It was your fault.
  • Christopher Robin explaining to his wife Evelyn about his stuffed animal friends and Heffalumps. She thinks he has gone absolutely bonkers... until Tigger and Eeyore splat against the window of the car. Seconds later, so does Piglet. Eeyore's complaint after everyone has finished talking? "My bum hurts." Well, you have just been smooshed against a car window - can't say we blame you!
    Christopher: Tigger! Eeyore! (Cue Piglet, who has been flying through the air and screaming the entire way, smacking into the window himself) Piglet!
    Tigger: That worked! I don't know how I do it!
    Piglet: (cheerfully greets Evelyn) You must be Christopher Robin's wife! How do you do?
    • Even funnier? Shortly before this, they were riding in a suitcase like a carriage and thrown so hard through the air that there's an audible "thwack" as they hit the windscreen of the car.
    • Just the way this conversation is framed. Evelyn finally demands to know exactly what's going on with Christopher, and he pauses, clearly realising how crazy it all will sound. We briefly cut away to Madeline and the gang on their adventures, and when we cut back, Christopher — having clearly decided that if he's in for the penny he might as well go for the whole pound — is casually rambling on about Tiggers and Heffalumps while his wife has a look on her face like he's grown some extra heads.
  • "Let's address the Heffalump in the room, shall we...?"
  • Pretty much anytime Eeyore opens his mouth. He's just so over-the-top morose and glum you can't help but smile.
    Eeyore: (thinking the older Christopher Robin is a Heffalump) It was nice of you to kidnap me.
  • When the stuffies first meet Madeline, she's pretending to be a tennis player at Wimbledon. And from that point onward, they refer to her as a Wimbledon champion.
  • Christopher telling Evelyn about his friends from the Hundred Acre Wood and Evelyn telling him that he "needs to quit".
    • Just the entirely casual way Christopher says things like "Of course, the good thing about a Tigger is that they're rubber at the top and bouncy at the bottom..." while his wife is looking like he's having a nervous breakdown.
  • Eeyore's introduction with Evelyn.
    Evelyn: Is that donkey talking?
    Christopher: That's Eeyore. Eeyore, this is Evelyn, my wife.
    Eeyore: Hello, Evelynmywife.
    Evelyn: (incredulous) Hello, talking donkey, how are you today?
    Eeyore: Don't get me started...
    • Piglet tells Christopher and Evelyn that Madeline is heading "Woozlewards". Before Christopher figures out that he means "Winslow", Evelyn — who, let's not forget, has only just been introduced to the world of eccentric talking stuffed animals — has a hilariously horrified look on her face that simply screams an inner monologue of "Oh God, are Woozles real as well?! What's a Woozle?! Is a Woozle about to eat my daughter?!"
      Christopher: Winslow!
      Evelyn: [Sudden realisation and relief] WiIIIIIINNNNSssslow! Winslow, yes, Winslow!
  • Madeline and her new friends have a tea party on the train when the refreshments trolley comes around:
    Serving Lady: Hello, miss. Can I get you anything?
    Madeline: Yes, I'd like... [Looks around at the animals, who are all "playing Naptime"] five cups of tea, please.
    Serving Lady: [A little taken aback, but playing along] ... Of course.
    Madeline: And some milk, and sugar, and...
    Pooh: [Sotto voce] And honey...
    Madeline: And honey, please. Lots of honey.
  • When the animals fail spectacularly at "playing Naptime" in the taxi, the driver is so startled that he ends up driving into a news stall, prompting a three-way argument between the cabbie, the newspaper seller, and a policeman who comes up to investigate, the latter two being understandably skeptical about the cabbie's demand to arrest the sweet-faced little girl with an armful of stuffed animals on the charge of "something spooky". Until this happens:
    Madeline: Excuse me, officer?
    Policeman: Yes, my darling?
    Madeline: [Pointing at a man crossing the street] That's my father there.
    Policeman: Okay, well off you pop. And be careful.
    Madeline: I will. Thank you, officer.
    Policeman: Thank you.
    Pooh: [Pleasantly] Thank you, orifice. What a nice man.
    [The policeman and the newspaper seller freeze in shock as Madeline quickly disappears; the cabbie, meanwhile has been distracted getting his license out]
    Cabbie: Right, here's me cabbie's license. If you don't believe me, that is a certificate of excellent — [Looks up, sees the stunned expressions on the other two men's faces] There's that face. I did that face! You seen him! You saw, didn't you, you saw! You have witnessed the peculiarity, haven't ya!
    Newspaper seller: [Almost frightened] What did we see?
    Cabbie: [Triumphant] The bear. Talking.
    Newspaper seller: Little teddy bear?
    Policeman: No, you didn't. You saw no such thing.
    Cabbie: I'm not making this up in my imagination!
    Newspaper seller: Talking!
    Policeman: No, it was not.
    Newspaper seller: It was!
    Cabbie: That's right! [To the policeman] Write it down!
    Policeman: It wasn't. We misheard.
    Cabbie: There was a pig as well!
    Newspaper seller: There was a pig...
    Cabbie: A talking pig.
  • There's something very funny about a frightened Piglet, arms full of haycorns that he refuses to drop despite them "weighing me down", running as fast as his little legs can carry him across the fields... while Christopher Robin follows him at a casual stroll, his long legs allowing him to match Piglet's pace without him even breaking a sweat.
  • Christopher Robin's fake fight with a Heffalump, in an attempt to prove the others he's really him.
  • Just watching Evelyn carrying Tigger, Piglet, and Eeyore around London in her arms.

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