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We are daring to be scaring!
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's Heffalump Halloween Movie is a 2005 direct-to-video Halloween movie in the Winnie the Pooh franchise, and the sequel to Pooh's Heffalump Movie.

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 before 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 away in March 2018.

This is also the final film in the franchise to be produced by Disneytoon Studios, with the next film being a Soft Reboot helmed by Walt Disney Animation Studios.

Pooh's Heffalump Halloween Movie contains examples of:

  • Actually Pretty Funny: Even when everyone is horrified that Pooh ate all the candy, Tigger makes an aside note about how he’s pretty impressed that Pooh was able to eat enough candy meant for the whole group on his own in such a short time.
  • Added Alliterative Appeal: The Gobloon's lair lies beyond the Creepy Cave, down the Slimy Slide, and in the Tree of Terror.
  • Arc Words: "Brave".
  • Big Damn Reunion: Lumpy bursting out of the Tree of Terror, which in turn leads to Roo's wish coming true and the two friends are happily reunited.
  • Big Eater: Pooh suffers this in the beginning, and in turn causes him to eat all the gang's candy.
  • Call a Smeerp a "Rabbit": Ghosts are referred to as "spookables".
  • Darker and Edgier: Very mildly so compared to the previous film, since the Halloween theme gives a slightly more ominous atmosphere especially since there seems to be a malicious threat to the heroes, whereas the previous film’s threat was always made plain to just be the characters’ fears.
  • Disney Death: Crossed with Dramatic Irony. When Roo and his friends think the Gobloon turned Lumpy into a "Jaggedy-Lantern", the audience knows this isn't the case and Lumpy is really alive, but Roo and the others don't.
  • Face Your Fears: Roo had to do this in the final act to track down the Gobloon and save Lumpy.
  • Failed Attempt at Scaring: Played for Laughs. At the beginning of the movie when Roo and Lumpy practice trick-or-treating at Rabbit's, the door flings open to reveal Pooh, Piglet, and Tigger wearing masks and shouting "BOO!"; instead of being spooked, Roo and Lumpy burst out laughing.
    Tigger: Oh, woulja look at that? We frightened 'em so much, they forgot to scream.
  • Fictional Holiday: Lumpy brings up various fictional Heffalump-themed holidays he celebrates, such as "Trumplet-Trumpet Day" and "Flapadoodle Eve".
  • Freak Out: When Roo shows the others what he believes to be Lumpy transformed into a jack o' lantern by the Gobloon, they promptly panic.
  • Friendship Song: "Brave Together" by Lumpy and Roo.
  • Ghost Story: Tigger's story about the Gobloon, as he shares about his sneakiness, turning whoever he catches into "Jaggedy-Lanterns" and how he grants one wish to whoever catches him.
  • Halloween Episode: The movie is set on Halloween.
  • Halloween Songs: "Trick R' Treating With Our Friends", as Tigger and the others teach Lumpy about Halloween.
  • History Repeats: As Roo notes in his retelling of Boo to You Too! Winnie the Pooh, Lumpy is going through the same arc Piglet did of facing his fears on his first Halloween spent with the others.
  • 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. When Roo believes to have caught the Gobloon in the Tree of Terror in the climax, he wishes for Lumpy to return.
  • Mistaken for Transformed: When Roo loses Lumpy and finds a jack o' lantern in Lumpy's likeness, this leads him to believing Lumpy was turned into one by the Gobloon.
  • Motor Mouth: Roo when he explains what he believes happened to Lumpy:
    Roo: We tried to catch the Gobloom 'cause we're gonna be brave together, and we found his tree, but I got scared and ran away, then the Gobloon got him and turned him into a jaggety lantern!
    (Beat)
    Tigger: Couldja start again from that first "gobloon"?
  • Nice Job Breaking It, Hero: Pooh’s gluttony causes him to eat all the candy Rabbit set aside for the group, setting the plot into motion.
  • No Antagonist: There is no major villain in the movie, instead relying on the gang facing their fears, especially Roo. The Gobloon seemed to be this, but he turns out to not exist; the mysterious figure Tigger saw in the beginning turned out to be Kanga.
  • Pass the Popcorn: Pooh eating all the candy, while Roo and his friends try to pull out a scared Lumpy from under the bed. This trope actually causes the whole adventure.
  • 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.
    • "Brave Together" is also replayed during the end credits.
  • Wham Line: Roo and Lumpy discover the misunderstanding that sparked the last act of the film:
    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.

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