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Tear Jerker / The New Adventures of Winnie the Pooh

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  • The episode "Find Her, Keep Her". In it, Rabbit cares for Kessie, a baby bluebird that grows up to be a surrogate daughter. Sooner or later, Kessie has to fly south for the winter, much to Rabbit's dismay.
    • What hits hardest is just the sheer amount of Does This Remind You of Anything? in this episode when it comes to parent-child relationships. Winnie The Pooh actually told a story of someone becoming a parent, raising a child, and then having to let that child go with a great deal of emotion and maturity.
      • When Kessie falls to an apparent Disney Death, Rabbit is clearly within an inch of the Despair Event Horizon as he cries, "Oh, Tigger... I never even told her I loved her!" Granted, she gets rescued by Owl and doesn't die, but still, that is some intense Adult Fear.
      • Kessie's last night with Rabbit. She asks him for a final bedtime story, which he quietly refuses on the grounds that she doesn't need him to read her a story — she doesn't need him for anything. Then he takes her stuffed rabbit into the other room and hugs it while Kessie sits by the fire and just sobs.
      • What leads into that scene is the Mood Whiplash inducing line of "Don't you think I know?", said by Rabbit in response to Tigger happily telling Kessie, who just learned to fly, that "there's nothing holding you back now!" Ken Sansom just hit it out of the park with the delivery of that line and the lines in the scene that followed.
        Rabbit: I changed my mind! You can fly! Just...don't go away, Kessie.
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    • The next episode to feature Kessie, "A Bird in the Hand", is depressing in its own right. Now a full-grown bluebird, she returns to the Hundred Acre Wood and Rabbit is under the delusion that it will be forever. He coddles her and treats her exactly the way he did when she was a baby, much to her displeasure. It's more painful than funny, and it's compounded by the fact that Rabbit really does appear to miss her more than she misses him — even after they reconcile at the end of the episode, she no longer calls him "Rabby."
  • "Stripes", in the New Adventures Of Winnie the Pooh. In a nutshell, Tigger loses his stripes after everyone forces him to have a bath...they then insist that he can't be a tigger, since tiggers have stripes. He sings a song toward the end of the episode, tearfully, about being "nothin' but stuffin'" and not having a name.
    What is a guy, when he's a nothin'
    Nothin' but stuffin', ain't even got a name
    I know I've changed, on the outside
    But on the inside, I feel the same
    Maybe someday, I'll know who I am
    But for right now... somehow
    I don't have a name
    • Tigger's line before that underscores what it's like to have an identity crisis, especially when you've lost something that was integral to who you are as a person.
      I'm not a tigger! I'm not a rabbit. I'm not a bear. And I'm sure not a piglet. I-I'm not an anything.
  • In "The New Eeyore," Eeyore decides to act more like Tigger in an attempt to be popular. However, his antics just end up annoying everyone else to the point where nobody wants to be around him. When Eeyore goes up to Tigger (who's upset that now he's the one getting bounced) and asks to play with him, Tigger angrily declares that he never wants to play with Eeyore again and walks off, leaving poor Eeyore alone on a hill.
    Eeyore: Tigger? (Sadly) Hoo hoo hoo hoo...
    • At the beginning of the episode, Eeyore sadly looks into the party at Pooh's house, feeling left out.
  • Eeyore's apparent depression in the beginning of "Donkey for a Day" and Piglet's increasing desperation and self-loathing for not being able to find a way to cheer him up.
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    • The fact that Eeyore's (seeming) glum attitude has reached such a level that the others actually call an intervention, worried what he's thinking. Piglet's very heartfelt lament on the situation to the others along with the dramatic music sells it. Of course for once Eeyore wasn't actually depressed, but still.
  • In "Winnie the Pooh and Christmas Too" when Pooh has lost the letter to Santa in a gust of wind. His cries of "Please come back! I'm supposed to take you to Santa!" are for naught. His face falls into an expression of pure despair. He's failed in his mission; and now has to trudge back home and tell everyone that they're not getting anything for Christmas. It all works out in the end, but you can't help but feel his pain.
    • Then we cut back to his friends, who are all anticipating their gifts from Santa, except Piglet, who acknowledges that Pooh won't make it back home in time for Christmas due to sending their letter. He spent the whole episode confused as to what he actually wanted for Christmas, now he knows, he wants Pooh.
  • In "Balloonatics", Christopher Robin lends Pooh a balloon and asks him to take care of it. It ends up in the hands of Rabbit, and he and Tigger and Piglet end up causing the balloon to deflate. Pooh finds out and the four decide to not tell Christopher Robin what happened. That night, Pooh has a nightmare that he's on trial and Christopher Robin is devastated that Pooh "broke" his balloon. Pooh is then thrown in a cage with the knowledge that Christopher will never speak to him again. This all comes after Pooh sang the sweetest, happiest song at the beginning of the episode about how he'll take care of the balloon.
  • Piglet's nightmare in "There's No Camp Like Home" proves just how badly his fears can get to him, as he dreams of Heffalumps and Woozles chasing him down and dogpiling him in a hellish environment and more or less eating him.
  • Pooh's pure innocence in this series (such as in the song in "Balloonatics") is bittersweet to watch after going through Break the Cutie big time in Pooh's Grand Adventure.
  • Kanga's Adult Fear in "Babysitter Blues" over Roo having gone missing. The situation degenerates to her sobbing and wailing over his absence.
  • In "Rabbit Marks The Spot", Rabbit plays a somewhat vindictive prank on the others leaving a fake treasure chest for them to find that he filled with rocks. After a creepy nightmare however, Rabbit convinces himself that everyone will hate his guts over the prank and decides to move away dejected. When the others drag him back to reveal the contents, he breaks down and begs for their forgiveness not realizing they failed to notice the prank and think the treasure inside is amazing.
    • It's actually better than that - the stunned silence of Rabbit's friends and the looks they exchange as Rabbit is breaking down suggest that they do indeed realize the prank but also realize that Rabbit is terribly sorry and wishes he could give them a true treasure. So to raise his spirits and show him that there are no hard feelings between them, they declare the rocks to be a true treasure because they could have a multitude of uses, making them as valuable a treasure as they could ever want, which they all thank Rabbit for and even give him his share of the treasure in the form of a rock they deem a "rare and valuable doorstop."
  • In "The Masked Offender", Tigger takes up a hero alter ego, and predictably causes more problems than he solves. The others, not recognising him, decide to pull a prank on the Masked Offender to take revenge, though after Tigger humiliates himself and the others laugh at him, until he takes his disguise off and walks off dejected.
    Rabbit: Tigger?! You're the Masked Offender?
    Tigger: Not anymore. I guess you were right, Piglet. No one wants a Masked Offender.
  • "Owl In The Family" starts with Owl becoming despondent, realising he has become estranged from his family despite spawning so many fond (and lengthy) anecdotes about them. Pooh and Piglet immediately try to soothe Owl's loneliness by sending letters to his family in their expected aimless way. Rather unexpectedly, they reach them and a proper family reunion occurs.
  • A meta-example, this was Hal Smith's final role as Owl, passing away shortly after the series ended. Rather fittingly and sweetly, Owl got the show's final episode "Owl's Well That Ends Well" devoted to him.
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