Tear Jerker / The New Adventures of Winnie the Pooh

• In "Pooh Oughta Be in Pictures", after Piglet sees that the carrot monster was just a costume and feels like a coward for being afraid of it and failing to rescue Pooh from it, he's scared by Pooh entering his home with a flash of Dramatic Thunder behind him. Despite Pooh's attempts to convince Piglet that he's a hero, he refuses his compliment and vows to stay under his couch for being a "worthless, no-good, can't-even-save-my-best-friend type of animal", tearfully saying "Goodbye... Pooh Bear...". The fact that Pooh leaves to the sound of Piglet sobbing makes it even more depressing, even when everything works out.
• 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" (quotes because Rabbit refused to be called daddy), 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.
    • 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 down 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's heartbroken response when Kessie finally flies away:
      Rabbit: I changed my mind! You can fly! Just...don't go away, Kessie.
  • 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 a nutshell, Tigger loses his stripes after Rabbit, Pooh and Piglet force him to have a bath...they then fail to recognize him as a tigger, since tiggers have stripes. He tearfully sings a song about being "nothin' but stuffin'" and not having a name toward the end of the episode.
  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.
  • 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.
  • Also from that episode is the scene where the Heffalump family discover that their house is missing, unaware that Tigger mistook it for a pile of firewood. Papa and Mama Heffalump’s reactions are humourous, with Papa doing a theatrical Gasp!, but then we cut to baby Junior’s reaction and it is anything but. The poor little guy sounds like he is literally on the verge of tears as he mourns the loss of what is more than likely the only home he’s ever known.
    Junior: Our home. Someone has stolen our home.
• 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 increasing fear in "Babysitter Blues" over Roo having gone missing. She returns home to find everyone searching for him and it slowly and painfully dawns to her that no one knows where he is.^note In reality he's just playing Hide and Seek under the bed After spending the whole day trying to find him, she begins bawling over his absence. (As an extra touch, an instrumental of Tigger's sad song from "Stripes" plays in the background.)
  Kanga: *sobbing* I just wish I knew where Roo was.
• 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^note except for Piglet, whom Tigger roped into being his sidekick, not recognising him, decide to pull a prank on the Masked Offender to take revenge, creating a fake monster out of sticky substances. Inevitably, the Masked offender humiliates himself when he gets stuck in it, and the other animals all laugh at his expense... which ends when Tigger 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.
  • Even worse, Piglet is the only one who doesn't take part in the scheme, and tries to stop Tigger from embarrassing himself. But he's too late and can only watch as the above happens.
  • Pooh immediately feels guilty for hurting Tigger's feelings with the prank, exclaiming "Poor Tigger!" as he watches his friend walk away.
• "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.
• The ending of "The Monster Frankenpooh", where Piglet curls up on the mantle of the fireplace and begs for forgiveness, thinking that everyone is really out to get him for creating the monster Frankenpooh, like in the story Tigger was telling about the Mad Scientist Dr Von Piglet. Tigger, Rabbit and Gopher all have to comfort him, reassuring him that the whole thing was just make-believe, no one is mad at him for real, and there is no monster.
• From "Tigger Is The Mother Of Invention," the destruction of Tigger's enormous implied-to-be-sentient wooden contraption. After it damages itself beyond repair to dig Piglet out of his snow-buried house, it expands and contracts violently with increasingly high-pitched and pained wheezing noises, before completely falling apart at the seams. This isn't helped by Tigger's heartbroken reaction afterward; staring at the remains in horror as if he's just watched someone close to him die.
  Tigger: M-my invention is... (chokes up) g-gone.
  Rabbit: (puts his arm around Tigger) There, there, Tigger. It gave its all to save Piglet.

---