Winnie the Pooh / Tear Jerker

The books

The ending of The House at Pooh Corner: Christopher Robin is leaving the Hundred-Acre Wood to go to boarding school—and it’s implied he knows he’ll have to grow up and leave his childhood friends behind. The characters don't know the specifics of why he’s leaving, but they band together and write a goodbye note. As they host a farewell party, Eeyore realizes that the boy wants to be alone with Pooh, and tells the others to leave. Christopher Robin then takes Pooh to 'An Enchanted Place at the Top of the Forest'. They talk together about doing nothing. Christoper Robin mentions that 'They don't let you do nothing. Not for long, anyway.' He tells Pooh of things he'll learn at school—about countries, Kings and Factors, eventually making him his best, most faithful Knight. Then the ending.
"Pooh, promise you won't forget about me, ever. Not even when I'm a hundred." Pooh thought for a little. "How old shall I be then?" "Ninety-nine." Pooh nodded. "I promise," he said.

Still with his eyes on the world, Christopher Robin put out a hand and felt for Pooh's Paw. "Pooh," said Christopher Robin earnestly, "if I — if I'm not quite —" he stopped and tried again — "Pooh, whatever happens, you will understand, won't you?"

"Understand what?" "Oh, nothing." He laughed and jumped to his feet. "Come on!" "Where?" said Pooh. "Anywhere," said Christopher Robin.

So they went off together. But wherever they go, and whatever happens to them on the way, in that enchanted place on the top of the Forest a little boy and his Bear will always be playing.
- Surprisingly, the ending was copied almost word for word in the ends of both The Many Adventures of Winnie The Pooh and Pooh's Grand Adventure. Slightly toned down yes, but the implications are still the same-and it's just as sad.

Disney's films

The Many Adventures of Winnie the Pooh

Has its own page.

Boo to You Too! Winnie the Pooh

Piglet sings a heartbreaking little ditty about how he feels isolated from his friends because of his fearfulness. Later when Pooh empathetically suggests they skip Halloween this year for Piglet, he only feels worse, thinking he's ruined everyone's fun.

Pooh's Grand Adventure

Has its own page.

The Tigger Movie

Has its own page.

Piglet's Big Movie

Has its own page.

Winnie the Pooh: Springtime with Roo

Rabbit's Bad Future if he succeeds in making the first day of Spring officially "Spring Cleaning Day". His friends will find him so overbearing and controlling that they’ll simply move away, leaving him completely alone.
- The scene is made even more painful to watch when at first he thought everyone leaving due to being an overbearing authoritarian was some kind of sick joke, only to be proven otherwise and become more desperate as the scene goes on. We even notice that the Hundred Acre Wood is becoming more barren as the scene moves on. What drives it home harder is that when he gets to Roo's and Kanga's place, he finds absolutely no one there... and in that moment of pure regret, he utters "What have I done? Where are all of my friends?" in this sad voice.
- Christopher Robin, Owl and Gopher aren’t seen or mentioned at all in this film, implying they left the Hundred Acre Wood as well, making Rabbit even more alone.
  - And just when he thinks he has a chance to redeem himself and give back the Spring holiday they enjoy... there's no such hope in Rabbit's Bad Future; when the gang left the Hundred Acre Wood, they somehow had taken ALL of their special Easter things from Rabbit, proving that they were serious about leaving him for good. However, it turns out to be All Just a Dream as Rabbit wakes up the morning and works to give back Easter to the denizens of the Hundred Acre Wood in order to prevent the future that would come.
The backstory explaining why he's come to hate Easter. After one especially overbearing year as the Easter Bunny, Tigger snuck off with the eggs and the gang went to do hunt them without him. This wasn't what broke Rabbit however. It was how much Roo loved Tigger playing Easter Bunny. He felt rejected since he wanted to make something nice for Roo, but couldn't compete with his Big Brother Worship of Tigger. Also, you can hear the sheer heartbreak coming from Rabbit when he asks how they could celebrate Easter without him, not to mention the sting he felt as a result being left out of the Easter Egg Hunt.
Rabbit: *solemn* Every Spring...I look forward to one thing most of all; being the Easter Bunny. You took that away from me.
- The look on Tigger's face upon hearing that sentence. When he heard that, Tigger knew all hope was lost, but he did try to apologize for making Rabbit feel like this anyway. Rabbit, however, wouldn't hear of it and so, Tigger went away dejectedly to tell Roo he wouldn't be getting his Easter Egg Hunt again.
Sometime after Tigger's failure to persuade Rabbit to give back Easter to the Hundred Acre Wood, we learn that while Roo was indeed sad over the loss of not getting to enjoy an Easter egg hunt, that was not what bothered him the most. The fact that Roo and the others had unknowingly broken Rabbit's heart since Tigger had outshone Rabbit as the Easter Bunny upset Roo the most. Despite the fact that Rabbit denied the Easter egg hunt, Roo doesn't have the heart to begrudge him for it.
- When Roo talks to Kanga about how Rabbit felt like he wasn't good enough to be Easter Bunny, you can see it on Rabbit's face that he feels terrible about his actions.

Pooh's Heffalump Movie

Lumpy is lost in the forest and trying to get back to his "mummy," but ends up caught in the heffalump trap set by Pooh and the others.
Lumpy: (to Roo, sobbing) You said they wouldn't be scary.
Roo: Oh, Lumpy. I'm so sorry. This is all my fault.
Lumpy: I want my mummy.
Poor Eeyore being Demoted to Extra and being forgotten about by the others until the end of the film.
Rabbit and the others tell Roo that he can't go on the heffalump "expotition," (because it's "fraught with danger" and you can't argue with a big word like fraught) which was his idea until Rabbit's Glad I Thought of It and then Kanga starts calling him.
Kanga: Roo!
Roo: You mean... I can't go? (ears droop, big frown)
Rabbit: I'm sorry, Roo.
Roo: Coming, Mom.

Winnie the Pooh (2011)

The trailers, with "Somewhere Only We Know" playing over them. Really hits home for people who have grown up with these stories and are adults now.
- the lines you can hear most clearly are:
...I knew the pathway like the back of my hand...
...Is this the place we used to love...?
and
...Oh simple thing, where have you gone...?
- This is the trailer.
- One TV spot flat out said: "They’re almost here. Admit it: You miss them".
The look on Pooh's face when his friends gave the jar of honey to the red balloon.
- And the resulting conversation with Eeyore.
Pooh: Ever have one of those days where you just can't win?
Eeyore: I know exactly how you feel.
Seeing that almost half the voice actors who worked on previous Pooh productions wouldn't return for this film, including Peter Cullen (Eeyore), Ken Sansom (Rabbit), and Andre Stojka (Owl), the former two in fact were reportedly disappointed they weren't called in for their roles. Especially since Sansom died the following year. Cullen however, was brought back for the Doc McStuffins crossover.