History TearJerker / WinnieThePooh

** The scene is made even more painful to watch when at first he thought everyone leaving due to being an [[JerkAss 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 [[MyGodWhatHaveIDone "What have I done? Where are all of my friends?"]] in this sad voice.

* [[Tearjerker/TheManyAdventuresOfWinnieThePooh Has its own page]].

* [[TearJerker/TheTiggerMovie Has its own page.]]

* [[Tearjerker/TheNewAdventuresOfWinnieThePooh Has its own page.]]

[[AC:Springtime with Roo]]

[[AC:Pooh's Heffalump Movie]]

* 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.

[[AC:Pooh's Heffalump Halloween Movie]]
* Meta example: this film marked the last time John Fiedler voiced Piglet. Fiedler died of cancer three months before the film was released (and only a day after Paul Winchell, Tigger's original actor, also passed away). His death also marked the EndOfAnEra, as Fiedler was the last original member of the voice cast still active in the series.

** One can give respects to Bud Luckey as Eeyore however, who passed away in 2018.
* A second meta example: [[EndOfAnEra this would be the last traditionally animated film in the]] Franchise/DisneyAnimatedCanon, and while CGI animation is alright, those who are fond of traditional animation would get a bit emotional.

[[AC:WesternAnimation/WinnieThePooh (2011)]]

* The ending of ''The House at Pooh Corner'': Christopher Robin is going away. It's implied he's going to boarding school, which means he won't see his friends again until he's an adult. The characters don't know the specifics, but they band together and write him 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.

* Rabbit's BadFuture 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 will all move away and leave him alone.

** One TV spot flat out said: "Admit it: You miss them".

** One TV spot flat out said: "Admit it: You missed them".

** Tigger did try to apologize for making Rabbit feel like this, but Rabbit wouldn't hear of it and so, Tigger went away dejectedly to tell Roo he wouldn't be getting his Easter Egg Hunt again.

[[AC:Disney/TheManyAdventuresOfWinnieThePooh]]

[[AC:Disney/TheTiggerMovie]]

[[AC:Disney/WinnieThePooh (2011)]]

* The ending of ''The House at Pooh Corner'': Christopher Robin is going away. It's implied he's going to boarding school, which means he won't see his friends again. The characters don't know the specifics, but they band together and write him 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.

!!Meta
* The ending of ''The Many Adventures of Winnie the Pooh'' is this mixed with a ''heavy'' dose of FridgeHorror if one considers the Christopher Robin in the stories to be ''the'' Christopher Robin (the son of Creator/AAMilne who inspired the original books). At the end of the film, Christopher Robin has to tell Pooh that he is about to start school and won't be able to play with him as often anymore. In real life, Christopher was [[ChildrenAreCruel bullied at school for inspiring the stories]], leading to some level of resentment of his father for (in his eyes) exploiting his playtime adventures and the public attention it netted him for life, until finally donating the stuffed toys he played with as a child to the editor of his first autobiography (though now they are at the New York Public Library). For all the fun he had with Pooh and pals, and the joy his father's stories have brought to children around the world, the suffering he was put through later in life is made all the more tragic by just how unnecessary it was.
* While the original stuffed toys have been repaired and preserved, Christopher's Roo was lost long ago.[[note]]Milne noted the toy was lost in Sussex after an incident with a dog.[[/note]] The original Kanga sits on display without her child.

* Rabbit's BadFuture if he succeeds in making the first day of Spring officially "Spring Cleaning Day". [[spoiler:His friends will find him so overbearing and controlling, that they will all move away and leave him alone.]]

*** And just when he thinks he has a chance to redeem himself and give back the Spring holiday they enjoy... [[DespairEventHorizon 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.]] [[spoiler: However, it turns out to be AllJustADream 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 look on Pooh's face when his friends gave the jar of honey [[spoiler: to the red balloon]].

* 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 BigBrotherWorship of Tigger.

* Meta example: this film marked the last time John Fiedler voiced Piglet. His death also marked the EndOfAnEra, as Fiedler was the last original member of the voice cast still active in the series. To add to the heartbreaking undertone, Fiedler died of cancer three months before the film was released (and only a day after Paul Winchell, Tigger's original actor, also passed away).

* Meta example: this film marked the last time John Fiedler voiced Piglet. He died of cancer four months after the film was released. His death also marked the EndOfAnEra, as Fiedler was the last original member of the voice cast still active in the series.

[[AC:Winnie the Pooh (2011)]]

** Tigger did try to apologize for making Rabbit feel like this, but Rabbit wouldn't hear of it and so, Tigger went away dejectedly saying that they'd never celebrate Easter in the Hundred Acre Wood again.

* A second meta example: [[EndOfAnEra this would be the last traditionally animated film in the]] WesternAnimation/DisneyAnimatedCanon, and while CGI animation is alright, those who are fond of traditional animation would get a bit emotional.

* Seeing that almost half the voice actors who worked on previous Pooh productions wouldn't return for this film, including Creator/PeterCullen (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 ''WesternAnimation/DocMcStuffins'' crossover and ''Disney/RalphBreaksTheInternetWreckItRalph2''.