Who's behind that mask you're wearing?
We can boo a spooky greeting,
Then we'll share the sweets we're eating,
When we're home from trick r' treating...
With our friends!
Pooh and his friends are getting ready for Halloween, and their new heffalump friend Lumpy is also there to celebrate it for the first time, though he's nervous. When Tigger spots a mysterious figure in the woods, he believes it's a legendary creature called "The Gobloon", which roams the woods on Halloween nights, turning every victim into "jaggedy lanterns" if he catches them. But if someone manages to catch him, they get to make a wish.
When Pooh inadvertantly eats all the candy, Roo and Lumpy decide to test their braveness and catch the Gobloon to make a wish for more. But when the two get lost and eventually separated, a case of misleadings lead Roo to rally the others to rescue his friend.
This movie features the entirety of Boo to You Too! Winnie the Pooh, this time told in flashback by Roo. This film is also the very last time John Fiedler voices Piglet before he passed away three months after the film was released. Fiedler died before his work was finished, so Piglet's new voice actor, Travis Oates, was brought in to finish the recording. This is also the final Pooh movie to feature David Ogden Stiers as the narrator before he passed on in March 2018.
Pooh's Heffalump Halloween Movie contains examples of:
- Arc Words: "Brave".
- Big Eater: Pooh suffers this in the beginning, and in turn causes him to eat all the gang's candy.
- Disney Death: Crossed with Dramatic Irony. The audience knows Lumpy is alive, but Roo and the others don't.
- Friendship Song: "Brave Together" by Lumpy and Roo.
- Halloween Episode: The movie is set on Halloween.
- Halloween Songs: "Trick R' Treating With Our Friends".
- Jump Scare: Pooh, Tigger and Piglet try this on Roo and Lumpy at the beginning. It doesn't work.
- Make a Wish: Those who manage to catch the Gobloon will get to make a wish.
- Rule of Three: The Gobloon's lair lies beyond the Creepy Cave, down the Slimy Slide, and in the Tree of Terror.
- Scary Flashlight Face: Tigger does this as he tells the story of the Gobloon.
- Transflormation: Anyone who is caught by the Gobloon will be turned into "jaggedy lanterns".
- Triumphant Reprise:
- "Trick R' Treating With Our Friends" returns in the end, as the animals celebrate Halloween at Kanga's house.
- A reprise of "Brave Together" is also sung during the end credits.
- Wham Line: Roo and Lumpy discover the misunderstanding that sparked the whole adventure:Roo: But where's your [jack o' lantern]?
Kanga: I'm so sorry, Lumpy. I did make one for you, but it must have fallen off my wheelbarrow.