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:
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.
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.
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!"
"All I did was I coughed," said Tigger. "He bounced," said Eeyore. "Well, I sort of boffed," said Tigger.
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.
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!"
"Three Little Piglets" is simply the funniest episode of the series, or any Winnie the Pooh series, for that matter. Pooh tries to read the story of the Three Little Pigs, but he and Tigger goof around with it in every way imaginable: Pooh continually attempts to insert honey into the story, the wolf becomes an annoyed Rabbit wearing a Big Bad Wolf costume, he mistakenly mixes in elements from other fairy tales ("the Big Bad Bunny was going to see his grandmother..."), the house of sticks becomes a house of cards, Tigger tries to save the pigs as the Masked Offender, and finally, Rabbit ends up getting drenched by a honey eruption.
Tigger's failed attempt to protect Rabbit from broken-mirror caused seven years of bad luck in "Luck Amuck" results in Rabbit getting buried under a mountain of watermelons (long story) - leaving Tigger to dig him out. Pooh comes across this crazy scene with his usual oblivious friendliness - which makes the following sequence ludicrously funny due to how totally unfazed and immediately accepting he is of the absurdity even while Rabbit is freaking out in front of him.
Pooh: "Tigger what are you doing?"
Tigger: "I'm digging for rabbit, Pooh-boy." <Tigger unearths Rabbit's head>
Pooh: "Well, you're in luck!" (cheerful chuckle) "There's one now!"
Rabbit (in the middle of an epic Freak Out): <insane sobbing/laughter> S-seven more years! <insane sobbing/laughter>
In scene where Tigger decides to run away so he wouldn't harm anyone with his bad luck, he puts ludicrous items in a trunk to move away with, including a sewing machine, Rabbits's bed and the kitchen sink. The funny part was that Tigger was packing RABBIT'S stuff.
The whole show had a good number of crowning moments of funny really; one that stands out is when Christopher Robin sees a "slusher movie" and Tigger reads the title, which is basically a summary of every slasher film/series plot...
Tigger: "The Slusher Who Slushed Everyone - And Then Came Back To Slush 'Em Again!"
Heck, the entirety of the Slusher episode was a huge Funny Moment. Especially when Tigger gets on Christopher Robin's nerves.
"Un-Valentine's Day" needs mentioning here, if not the entire episode then at least...
Piglet: I AM CUUUUUUUUUPPIIIIIIIDDDDDDD!!!
The western episodes. For example, this exchange from The Good, The Bad and the Tigger:
Tigger: I am the Tigger with no name.
Pooh: I am the Pooh with a name! If only I could remember it. Oh bother.
A reminder to those who don't get it: Pooh's name is Edward Bear, except odds are almost no one who watched this knew that...
The scene in the Christmas Special when Pooh, dressed up as Santa Claus, is stuck in Tigger's chimney. Tigger thinks it's really Santa and starts bouncing gleefully around: "SANTY'S COMIN' DOWN THE CHIM-EN-Y!" It really has to be seen to be appreciated.
Not to mention Tigger "helping" Santa-Pooh get back up the chimney.
Tigger (getting a broom and fulcrum): "Hey, anything for ol'-Saint Nick! A one... a two... A FIRE!"
Catapults Pooh back up the chimney and flying far, far away.
The gang's feeble efforts to hide the fact they deflated the balloon Christopher Robin lent Pooh include Rabbit painting a boulder red (which evidently feels much heavier than the average balloon), Piglet dressing as a balloon (with his head and limbs still visible), and Tigger making a bubble gum bubble (which doesn't last very long).
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 for goodness sakes!
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. What a JerkassCompanion Cube!
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: "Eeyore, do you ever have one of those days where you just can't win?"
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. Guess what the gang first mentions to Owl? How good his speech was.
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 sounds almost akin to Dom De Luise.
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. What a heck of a Disney Acid Sequence.
The "issue/achoo" sequence with Owl, Pooh and Eeyore.
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.