SPOILERS: Classic Disney magic, now over 25 years old.
We see Halloween Town as a fantasy world filled with monsters and supernatural beings associated with the time of year.
Jack Skellington, the "Pumpkin King” and prime minister of the town, leads the town in organizing the annual Halloween celebrations. However, privately Jack has grown weary of the same routine year after year and wants something new and diverting.
Wandering in the woods he stumbles across seven trees containing doors leading to towns representing various celebratory holidays, and opens the portal to Christmas Town.
Awed by the unfamiliar holiday, Jack returns to Halloween Town to show the residents his findings, but they fail to grasp the idea of Christmas and compare everything to their ideas of Halloween
They do relate to one Christmas Town character; a red lobster-like king who flies at night named "Sandy Claws".
Jack goes to his tower to study Christmas in order to find a way to rationally explain it, but cannot. He decides that it's unfair for Christmas Town alone to enjoy the holiday and announces that he and the citizens of Halloween Town will independently take over Christmas this year.
Jack assigns the citizens of Halloween Town Christmas-themed jobs, based upon the ones in the real Christmas, including singing carols, making presents, and building a sleigh to be pulled by skeletal reindeer. The tasks and outcomes may look similar, but they are not.
Sally, a beautiful rag doll that is secretly in love with Jack, experiences a vision that their efforts will end in disaster, but Jack dismisses this and assigns her the task of sewing him a red coat to wear.
He also tasks Lock, Shock and Barrel, a trio of mischievous trick-or-treating children, to abduct Santa Claus and bring him back to Halloween Town.
Jack tells Santa he will be bringing Christmas to the world in his place this year. Jack orders the naughty trio to keep Santa safe, but the children instead deliver Santa to Oogie Boogie, a gambling-addicted bogeyman, who plots to play a game with Santa's life at stake. Sally attempts to rescue Santa so he can stop Jack, but Oogie captures her as well.
Jack departs to deliver presents to the world, but the Halloween-styled gifts terrify and attack the populace. As concerns over "Santa's" behavior grows, the military takes action and shoots down Jack, causing him to crash in a cemetery.
While the residents of Halloween Town think he's been blown up, Jack has survived, and he bemoans the disaster he has made of Christmas, he finds he enjoyed the experience nonetheless, reigniting his love of Halloween.
Jack returns to Halloween Town and finds Oogie's lair. Oogie tries to kill Jack, but Jack pulls apart the thread holding his cloth form together, revealing a massive pile of bugs that fall into Oogie's cauldron and are killed. Jack apologizes to Santa for his actions, and Santa assures Jack that he can fix things and returns to Christmas Town.
As Santa replaces the Halloween-style presents with genuine ones, the townspeople of Halloween Town celebrate Jack's survival and return.
Santa then visits Halloween Town and brings them a Scissorhandian snowfall for the residents to play with, which in a way, fulfills Jack's original dream. In the graveyard, Jack and Sally declare their love for each other.
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