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  • When Christopher Robin tries telling everyone about Eeyore's missing tail:
    Christopher Robin: Something tragic has befallen a member of our community! I present to you, Exhibit A! [camera pans to Eeyore]
    Kanga: Oh! That is tragic.
  • Eeyore's various replacement tails, which include a weathervane, a chalkboard (with "TAEL" written on it, no less), an anchor, and a paragraph.
  • When all the group but Piglet gets trapped in a hole, Rabbit asks him if he could knot the ropes together.
    Piglet: I cannot.
    Rabbit: Ah, so you can knot?
    Piglet: No, I cannot knot.
    Rabbit: Not knot?
    Pooh: Who’s there?
    Rabbit: Pooh!
    Pooh: Pooh who?
  • B'loon's appearances just keep getting funnier and funnier because everyone's treating it like an actual character when all it does is float around.
    • Rabbit and Piglet's panicked "Wait! B'loon! Don't leave!" and "You're the only one who can get us out of here!" is particularly funny — they honestly sound on the verge of despair because they think the balloon is deserting them in their time of need.
    • Right after the balloon "deserts" them, Eeyore just says in the most depressed, drawn out and monotone way he can muster, "We're all gonna die", while everyone else just goes silent and looks at him in horror. Rabbit especially is visibly frozen for a few seconds. It becomes even funnier when you realize he just said this in front of a small child (Roo) and when you consider that this is Winnie the Pooh.
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    • And then B'loon, despite being a normal, non-sentient balloon, manages to end up taking all the credit for finding Christopher Robin and getting the animals out of the pit, and then floats away with the prize honey.
      • Icing on the cake: As B'loon floats away with the honeypot tied to its string, Pooh just stares at the scene with a look of total dumbstruck defeat. Then when Eeyore walks up to him, Pooh makes this comment:
        Pooh: Ever have one of those days where you just can't win, Eeyore?
  • When the entire gang (save for Piglet) falls into the Backson pit and Piglet is scared to go into the woods and search for help, Owl flies out of the Backson pit, gives Piglet a speech to send him on his way, and then flies back into the pit. The first thing the gang mentions to him afterwards is how good his speech was.
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  • Rabbit's horrified expression when Piglet off-handedly produces a rope to rescue the six of them from the pit... and then cuts it into six pieces, one for each of them.
    Rabbit: Why didn't we think to bring a rope?
    Piglet: Well, there is this rope!
    [cue an Epic Face from Rabbit]
  • Eeyore got a lot of funny moments in the movie, but many of them were simply giving flat or wide-eyed looks to the audience.
    Eeyore: Something tells me I was better off with Tigger. *The others throw his anchor "tail" into the pit* Yep.
    • Let's not forget this:
      Eeyore: [singing] Found this anchor over there, now it's on my derriere. Not that anybody'd care.
  • The Stinger. All of it. The Backson was real all along, looks exactly as described... and is picking up the objects left in the forest to return them to their rightful owner before falling into the pit.
    • Not to mention his voice, which is that of gentle and enthusiastic Huell Howser.
    The Backson: Oh my gosh! Is this a pit? I think I'm in a pit!
  • Tigger bouncing B'loon because B'loon was "sneaking up on" Pooh. And the tide turns soon afterward when B'loon "sneaks up" behind Tigger, attaches to him with static electricity, and so on. When Pooh suggests that it seems B'loon wants to stick with Tigger, suddenly Tigger gets excited about the idea of having a sidekick! "But no— what if something happened to the poor guy?"
  • Tigger dragging Eeyore along as his "Tigger 2". The entire sequence. And Eeyore cleverly escapes it by diving underwater and breathing through a reed. Later, while they're in the pit together, Eeyore makes a comment that emphasizes how much he didn't enjoy it (and could even double as an insult, but he didn't really say it in a mean-spirited way):
    Eeyore: The most wonderful thing about Tiggers is... you're the only one.
  • Pooh's hunger-induced auditory, and then visual, hallucinations (possibly just imaginings). What a heck of a Disney Acid Sequence.
    • It starts with him imagining his friends with a Verbal Tic around the word "honey".
      Rabbit: "I can't wait to see the honey on that Backson's honey when he falls into our honey!"
      Owl: "That cheeky honey will honey twice before honeying our honey again."
      Roo: "After we honey the honey, can I honey a honey?"
      Kanga: "Uh-uh-uh. No honey before honey, honey."
      Piglet: "Honey up, Pooh, we have to honey."
      (they all say stuff about honey at once)
      Narrator: "As Pooh watched the honey honey away, his...(then every word turns into "honey")"
    • When Pooh sees himself made of honey, he eats the head off, rationalizing that "he's just made of honey, so I guess I'll eat him too." The headless honey-Pooh then shrugs.
    • "If everything is honey and I am what I eat, I must be made of honey and life is very sweet."
  • Owl, Rabbit, Kanga, and Piglet trying to corner what they believe to be the Backson:
    Kanga: Ohh, no, no, nonononoo... [lifts up Roo, grinning ear to ear] I'm with child!
    Roo: [completely deadpan, glaring down at Piglet] Send the pig!
    • And after Piglet faints, Rabbit suggests they all go, but when they hear Pooh, the scared face Rabbit makes is so priceless.
  • During the Backson song, one of Kanga's ideas for a horrible thing the monster does is stealing a person's youth, including an Imagine Spot of the Backson holding a mirror up to her face, where her reflection becomes old and wrinkly. Her resulting scream, and the idea that Kanga may be terrified of old age, is hilarious.
    • Owl's thoughts about what Backsons do include scribbling in books and messing up your Christmas decorations and Tigger's is making you sleep too late. They also seem to have a problem with the Backson being busy, even though Rabbit and Owl like to be busy.
    • One lyric is "Its nose is black, its fur is blue, I swear that everything I tell you is not made up!"
    • One lyric is "they spill your tea!" complete with an imaginary Rabbit getting tea spilled in his lap.
  • The whole "issue" gag between Pooh, Eeyore, and Owl.
    Owl: Yes, well, the thing to do is as follows: First, issue a reward—
    Pooh: Gesundheit.
    Owl: I beg your pardon?
    Pooh: Well, you sneezed just as you were going to tell me what the first thing to do was.
    Owl: I didn't sneeze.
    (Pooh and Eeyore look at each other)
    Eeyore: Oh, you did, Owl.
    Owl: No, I didn't! You can't sneeze without knowing it!
    Owl: As I was saying, first: issue a reward—
    Pooh: [whispering to Eeyore] He's doing it again. [to Owl] You must be catching a cold.
    Owl: No, no, no! I'm not catching a cold! The word is ISSUE, not AH-CHOO! And 'ah-choo' isn't even a word! It's just some sort of sneezy sound, like 'Ah-choo!'
    Pooh: Perhaps you should lie down, Owl.
    Owl: Oh! (facepalms and falls over backwards)
  • During the "setting-the-trap" montage, Rabbit surfaces from the water and makes a variety of odd gestures to communicate a plan to Pooh and Piglet. The gestures are funny enough. What really nails it, though, is when Pooh and Piglet (possibly like the audience) don't understand one bit of what Rabbit is trying to tell them. So they just look confusedly at each other and then wave at Rabbit cheerfully. Cue an epic Face Palm from Rabbit.
  • When Christopher Robin returns and reveals that Owl was wrong about the Backson, the others all slowly look at Owl and glare at him. Owl laughs nervously as he realizes his mistake... and runs like hell.

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