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The original novels

  • In The House at Pooh Corner Piglet and Pooh fall into a deep hole which they eventually decide must be a trap dug by a Heffalump. Pooh suggests that when the Heffalump comes along, they should try to confuse it by claiming that they dug the trap for him. Piglet lapses into a dream sequence about all the brave and witty things he's going to say to the Heffalump... and then when Christopher Robin finds the hole, a panicking Piglet mistakes him for the Heffalump, and all the brave, witty things he was planning on saying end up in a confused muddle:
    "This is a trap for Poohs, and I'm waiting to fall into it, ho-ho, what's all this, and then I say ho-ho again."
    "What?" said Christopher Robin.
    "A trap for ho-ho's," said Piglet huskily. "I've just made it, and I'm waiting for the ho-ho to come-come."
    • The original "heffalump trap" chapter from the first book is no less funny, with Piglet seeing Pooh in the trap with his head in a honey-pot, mistaking him for a heffalump, and sounding the alarm:
  • Just about all of Tigger's antics in the second chapter of The House At Pooh Corner ("In Which Tigger Comes To The Forest And Has Breakfast").
    • He thinks the tablecloth tried to bite him, and when Pooh says that it didn't, Tigger says, "It tried."
    • When he eats a thistle, he thinks that it's painful because it's too hot. Later, he says, "What were those hot things called?"
  • Eeyore's sole attempt at writing a poem in the last chapter of The House At Pooh Corner. He's genuinely trying to write a "goodbye" poem to Christopher Robin, but the poem ends up being mostly about Eeyore not being able to find any good rhymes:
    Christopher Robin is going.
    At least I think he is.
    Where?
    Nobody knows.
    But he is going-
    I mean he goes
    (To rhyme with "knows")
    Do we care?
    ( To rhyme with "where")
    We do
    very much.
    (I haven't got a rhyme for that "is" in the second line yet. Bother.)
    (Now I haven't got a rhyme for bother. Bother.)
    Those two bothers will have
    to rhyme with each other
    Buther.
    The fact is this is more difficult than I thought
    I ought-
    (Very good indeed)
    I ought
    To begin again,
    But it is easier
    To stop.
    Christopher Robin, good-bye
    I
    (Good)
    I
    And all your friends
    Sends-
    I mean all your friend
    Send-
    (Very awkward this, it keeps going wrong)
    Well, anyhow, we send
    Our love.
    END.
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    • They all sign it, and their signatures are shown in picture, to be PooH, PIGLET, WoL, RABBIT, KANGA, EOR, BLOT (Tigger, who just hits the page with an ink-covered paw) and SMUDGE (Roo, who appears to have put his feet into the ink and walked on the page).
  • The chapter where Kanga and Roo come in, initiating a Zany Scheme by Rabbit to get rid of them, involving Rabbit kidnapping Roo while Piglet takes his place inside her pouch. When Kanga discovers Piglet, she decides to just go with it and pretends to think that he's Roo, so that he grows increasingly frustrated as she gives him Roo's medicine and bathes him, all while insulting him:
    ...you know what I told you yesterday about making faces. If you keep making faces like Piglet, you will grow up to look like Piglet—and then think how sorry you will be.
  • When Eeyore accuses Tigger of bouncing him into the river.
    "It's like this, Christopher Robin," said Rabbit. "Tigger — "
    "No, I didn't!"
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    • And further on:
    "All I did was I coughed," said Tigger.
    "He bounced," said Eeyore.
    "Well, I sort of boffed," said Tigger.
  • Owl's house is originally called "THE WOLERY", but then Eeyore sits on the sign and it becomes "THE SMUDGE". Owl coughs at Eeyore in irritation when he sees this. Then Eeyore marches off to show the other animals the new house he found for Owl, with the greater part of "THE WOLERY" on his behind.
  • Eeyore's hilarious comments about pretty much everything.
    • "Gaiety, song and dance, here we are and there we are."
    • "We can play here-we-go-gathering-nuts-in-May with the end part of an ant's nest."
    • "I don't want to complain, but I just do complain."
  • Pooh tries to put himself to sleep by counting Heffalumps instead of sheep but every Heffalump takes a pot of his honey, and when "the five hundred and eighty-seventh Heffalumps were licking their jaws, and saying to themselves, 'Very good honey this, I don't know when I've tasted better', Pooh could bear it no longer".
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Return To The Hundred Acre Wood

  • David Benedictus's Return To The Hundred Acre Woods is a bit uneven as a whole, but has some really hilarious parts, one standout being when Owl tries to solve a crossword puzzle and gets stumped by "Big bird (3 letters)." He ends up writing "EGL," which he suspects is wrong — but try as he might, he can't squeeze "OSTRIDGE" or even "HORK" into three letters.
  • Rabbit trying to run a Census for the animals of the forest, with predictably disastrous results. Even the animals who are willing or even eager to go along with it, like Tigger, don't really seem to grasp the spirit of the thing:
    "Tigger," said Rabbit, "let’s begin with you."
    "Yes, let’s," said Tigger, bouncing a little, even though he had no idea what was to be begun. He liked to be asked to do things, and he liked to be asked to do them first, and he always said 'yes' because it is much more interesting when you do.
    "Name?"
    "Tigger."
    "Spell it."
    "T-I-GRRRRRRRRR..." And Tigger emitted a ferocious growl.
    "Put your handkerchief in front of your mouth when you do that, dear," said Kanga.
    "Age?"
    Tigger counted his paws, and then his whiskers, and then Roo’s paws and whiskers, and then Kanga’s paws and whiskers.
    "Don’t know," he said at last.
    "I’ll put down twelve," said Rabbit.
    "Hooray!" cried Tigger. "Then I can have a birthday!"
    • Christopher Robin, of all characters, unleashes his inner Deadpan Snarker when Rabbit tries to get him to take part in the census.
    Christopher Robin: You already know my name.
    Rabbit: Spell it.
    Christopher Robin: I-T.
    • It gets worse when he tries to include all his Friends-and-Relations in the Census, because he can't keep track of which ones are Relations and which ones are Friends. In the end he tries solving it by inviting them all to his house and offering carrots to Relations and shortbread to Friends — only to discover that nobody wants carrots, so they all say they're Friends in order to get shortbread instead.

Disney features

  • In Piglet's Big Movie, Pooh is distracting Kanga with small talk about whether the animal sitting in a nearby tree is a bird or a fish. The situation is taken from the original novel, but in the movie, Tigger (who was not present for the scene in the book) intervenes with "It looks kinda wiggly! It could be a jellyfish! ...I think it's more of a peanut-butter-and-jellyfish, isn't it?" All of which is amusing, but the real Funny Moment comes in the next scene, where the camera zooms in on Kanga's house... right past a tree where a really happy-looking fish is sitting on a branch.
  • When Pooh and the gang found Piglet's diary within Piglet's Big Movie, they come across a drawing of Rabbit, who then promptly becomes annoyed and says "That doesn't even look like me!" Said drawing depicts Rabbit pulling that exact same facial expression.
  • Springtime For Roo has Pooh and the others spring cleaning for Rabbit, after coming in contact with too much dust, Pooh begins the most dramatic, overblown sneeze "that has ever been sneezed in the Hundred Acre Wood", even adding a whimsical little musical number inbetween it all.
    Pooh: Sniffity sniff, whistley wheeze,
    Here it comes, a great big sneeze...
  • In Pooh's Heffalump Movie, Lumpy tells Roo that his name is "Heffridge Trumpeter Bumpet Heffalump the Fourth". Roo asks him how he remembers all that, and Lumpy replies "I can't!"
    • A lot of Lumpy's earliest scenes qualify, since he's so much of an off-the-wall Cloudcuckoolander Keet that even Roo has difficulty keeping up with him.
    • During the rest of the gang's attempts to pursue a heffalump, Rabbit tries to drive one out with his "heffalump call", leading Pooh and Piglet to mistake him for one and capture him in a net:
    Piglet: Have you noticed that heffalumps look a lot like rabbits?
    Rabbit: *folding his arms inside net* And why do you think that is, Piglet?
    Piglet: Oh d-d-d-d-dear! The heffalump knows my name!

Comics

  • For some odd reason, Pooh is characterized as being an absolute jerk in the newspaper comic, saying really mean things to his "friends," and generally acting in a very self-centered manner, and sometimes it's not really clear if it's out of naivete or genuine malice. This leads to a lot of out-of-character moments, and they're pretty funny.
    • August 27th
    Pooh: You take yourself too seriously, Eeyore.
    Eeyore: You mean I should learn to laugh at myself?
    Pooh: Why not? Everyone else does.
    • March 28th
    Pooh: Excuse me, but...you're sitting in my spot.
    (Panel shows that Pooh and Piglet are in a very, VERY wide open space with plenty of space for Pooh to sit)
    • June 11th
    Pooh: Happy Birthday, Eeyore! We're having a birthday party for you this afternoon!
    Eeyore: Oh no! Why do you do this to me, Pooh? You know how parties depress me. All that jollity and merriment.
    Pooh: We know how you feel about birthday parties, Eeyore! That's why we didn't invite you!
    • June 12th
    Eeyore: How was my birthday party I wasn't invited to yesterday?
    Pooh: We had a lovely time, Eeyore!
    Eeyore: I really don't understand how a sensitive person like you can have a good time at a party. I've never gone to a party in my life that didn't turn out to be boring and depressing.
    Pooh: That's funny, Eeyore, the parties you don't go to are a lot of fun.
    • August 8th
    Piglet: I think brains are more important than beauty.
    • September 29th
    Pooh: You're looking very well today, Tigger! And I'll say the same thing to you, Eeyore. Tigger's looking very well today!
    • September 2nd
    (Piglet stands at Echo Point)
    Echo: Hello!
    Piglet: Hello!
    Pooh: Can't you do anything right?
    • June 7th shows that Piglet can be a jerk back.
    (Pooh finishes some exercises)
    Pooh: Whew! Self-improvement is sure hard work, Piglet.
    Piglet: You should have picked somebody who doesn't need so much improvement.
    • January 26th
    Owl: Pooh, I'm giving a speech at the Owl's Club tonight, and I need to keep track of how long I talk.
    Pooh: I've got just the thing for you, Owl.
    (Pooh hands him a calendar)
    • January 11th
    Pooh: (With his arm in a sling) Piglet, would you mind holding this nail straight for me?
    Piglet: Sure, Pooh.
    Pooh: It's hard to fix things with one hand in a sling.
    Piglet: What happened to your hand?
    Pooh: I hit it with the hammer.
    (Pooh is winding up the hammer, and Piglet has an Oh, Crap! expression)
    • March 5th
    Pooh: Hello, Piglet! I was just about to have my lunch! Come on in! You can watch me eat!
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