Ash and His Friends go to Halloween Town a dream world filled with dark creatures such as deformed monsters, ghosts, ghouls, goblins, vampires, werewolves and witches. Their old ally, The Pumpkin King, Jack Skellington, leads them in a frightful celebration every Halloween, but he has grown tired of the same routine year after year. Wandering in the forest outside the town center with his ghost dog, Zero, he finds a cluster of trees each with a door which represents a certain annual holiday. Jack is drawn to the tree with the Christmas tree-shaped door and opens it which leads to a portal to "Christmas Town". Impressed by the feeling and style of Christmas, Jack presents his findings of the holiday to the Halloween Town residents. They fail to grasp his meaning and compare everything he says to their idea of Halloween. Jack undertakes several experiments to try to understand Christmas logically, but he becomes frustrated when he fails to understand. However, he realizes that just because he can't understand Christmas does not mean he still can't enjoy it; so he announces to Halloween Town that this year they will take over Christmas.
Jack's obsession with Christmas leads him to usurp the role of Santa Claus, known to him as "Sandy Claws". Every resident is assigned a task, while Sally, a rag doll woman who was created by the town's mad scientist, has romantic feelings towards Jack. However, when she is alone, she has a premonition of Jack's Christmas ending badly. When she tries to warn Jack of the imminent disaster, he misinterprets her anxiety to mean that she is worried when given the responsibility to make Jack's Santa costume. Meanwhile, Jack assigns Lock, Shock and Barrel, a trio of mischievous children, to bring Santa to Halloween Town. When he arrives, Jack tells him of his plan that he will take over Christmas this year, much to Santa's protests. After this and against Jack's instructions, and largely for their amusement, the trio deliver Santa to Oogie Boogie, a gambling-addict bogeyman who plots to play a game with Santa's life at stake.
Christmas Eve arrives and Jack prepares to embark into the sky on a coffin-like sleigh pulled by skeletal reindeer. Sally tries to stop him by releasing fog juice, but Jack is inspired by Zero's glowing nose and orders the ghost dog to lead the team. He begins to deliver presents to children around the world, but the gifts (shrunken heads, Christmas tree-eating snakes, etc.) only terrify the recipients. Jack is believed to be an impostor attempting to impersonate Santa. The army is alerted, and, using searchlights to spot him, they open fire on him with artillery. Jack believes at first that the shells are merely fireworks, set off to thank him; by the time he realizes the truth, it is too late. The sleigh is shot down and Jack is presumed dead by Halloween Town's citizens, but in fact he has survived the crash, landing in a cemetery. Although he is depressed by the failure of his plan and the damage it caused, he realizes that his Christmas adventure has helped him to rediscover his love for scaring people. Having come up with new ideas for next Halloween and wanting to "set things right", he rushes back to Halloween Town.
Meanwhile, Sally attempts to free Santa, but fails and is also captured by Oogie. Jack slips into the Oogie's lair and frees both Santa and Sally just before Oogie can drop them into a fire pit. Jack then confronts Oogie, who sets off several lethal traps, which Jack nimbly avoids. Oogie tries to escape, but Jack uses a single loose thread hanging from the bogeyman's sewn rag structure to rip him open, exposing the bugs that he is made of. He falls apart, and most of his bugs fall into the fire pit. The last one is squashed by Santa, who then reprimands Jack before setting off to deliver his presents to the children of the world. Jack asks Sally how she got into Oogie's lair in the first place and he realises that she was trying to help Jack because she has feelings for him. When Jack and Sally return to Halloween Town, the citizens rejoice that Jack is alive. Moments later, Santa is seen in the sky, making snow fall over Halloween Town to show that there are no hard feelings between himself and Jack. The townspeople are confused by the snow at first, but soon begin to play happily in it. Jack follows Sally out into the graveyard after seeing the Doctor with his new creation. Jack and Sally sing a romantic song together and then share a passionate kiss on top of the spiral hill in the graveyard. Zero watches them from afar before flying into the night sky forming a bright star shape and ending the film.
- Jessie, James, and Meowth of Team Rocket are working for Oogie Boogie in this film.
- Ash and his friends have met Jack Skellington and faced Oogie Boogie before in Pooh's Adventures of Happily Ever After and then again with Team Rocket teaming up with Oogie Boogie in Littlefoot's Adventures of Beetlejuice, Littlefoot's Adventures of Free Willy 2: The Adventure Home, Littlefoot's Adventures of All Dogs Go to Heaven 2, Littlefoot's Adventures of Who Framed Roger Rabbit, and Littlefoot and The Adventures of the Great Mouse Detective. Jack Skellington has also faced Team Rocket again with Oogie Boogie before in Littlefoot's Adventures of Mighty Morphin Power Rangers: The Movie, Littlefoot's Adventures of Space Jam, Littlefoot's Adventures of Mulan, and Littlefoot's Adventures of 101 Dalmatians.
- This film was a request from BowserMovies1989.
- Unlike BowserMovies1989 and DisneyAnimeManiac's versions of Pooh's Adventures of The Nightmare Before Christmas, this is a PAL film with PAL bits from Pokémon 4Ever and NTSC bits from the Pokémon films 1, 2, 3, and 5.
- Also unlike in BowserMovies1989 and DisneyAnimeManiac's versions of Pooh's Adventures of The Nightmare Before Christmas (in which Pooh and his friends stayed in Halloween Town at the beginning), Ash and Pikachu follow Jack into the woods while Misty, Togepi, and Brock stay in Halloween Town at the beginning of this film.
- This is the second Pokémon crossover film in which Winnie the Pooh is briefly mentioned. He was mentioned alongside Littlefoot by Brock while Ash and the gang reunited with Jack at the beginning of this film. The first Pokémon crossover film Pooh was briefly mentioned in was Ash's Adventures of Aladdin, where Ash and the gang first visited Agrabah at the beginning.
- Part 1: https://docs.google.com/file/d/0B7mSo0UN1fEOeURJVGdsakVTSk0/edit?pli=1
- Part 2: https://docs.google.com/file/d/0B7mSo0UN1fEONkloNGZPeFJHWW8/edit?pli=1
- Part 3: https://docs.google.com/file/d/0B7mSo0UN1fEOSHR6N2xycHgzOGs/edit?pli=1
- Part 4: https://docs.google.com/file/d/0B7mSo0UN1fEORUUwV2lIS3R0Mlk/edit?pli=1
- Part 5: https://docs.google.com/file/d/0B7mSo0UN1fEOcFkxTmxHaW9iYTA/edit?pli=1
- Credits: https://docs.google.com/file/d/0B7mSo0UN1fEOdDZtc2YtdkQyaWs/edit?pli=1