Catherine O'Hara

It's summer vacation, but two high schoolers have been instructed to clean the (empty) swimming pool. As they sweep the pool, they initially discuss school life, love and makeup. But it isn't long before their worries begin to overflow and their thoughts intersect. —jakkepoes

Halloween Town is a dream world filled with dark creatures such as deformed monsters, ghosts, ghouls, goblins, vampires, werewolves and witches. A skeleton known as The Pumpkin King, named Jack Skellington (Chris Sarandon), leads them in a frightful celebration every Halloween, but he has grown tired of the same routine year after year. Jack laments that he has grown weary of the sounds of screams and does not covet the crown of Halloween Town anymore. The town prides itself on its ability to scare people and consider it to be their proud tradition. 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. The holidays include Valentine's Day, St Patrick's Day, Thanksgiving, Easter and Christmas. Jack is drawn to the tree with the Christmas tree-shaped door and opens it which leads to a portal to "Christmas Town". Jack finds that the town is covered in snow and yet everything is colorful unlike the morose Halloween Town. Nobody is dead, children are throwing snowballs at each other, and people are busy building toys. Jack feels the warmth of Christmas, of family gathering together to celebrate the festival. Everyone is smiling and they are having fun. The monsters are missing, and the nightmares cannot be found, and as such there are good feelings all around. Meanwhile, back in Halloween town, Jack's absence is discovered and the Mayor panics as it is only 364 days till next Halloween and only Jack makes all the decisions. An alarm is sounded. 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. The residents cannot understand the concept of a present, or candy inside a hanging sock, or a Christmas tree decorated with baubles and lights. Although there is one character in Christmas Town they can relate to, a mighty lobster-like king, who is known as "Sandy Claws". Jack undertakes several experiments to try to understand Christmas logically, but he becomes frustrated when he fails to understand. He dissects and analyzes each and every aspect of Christmas in a lab but still cannot make any sense of it. He reads all books on the subject of Christmas and memorizes all the Christmas Carols, and yet the meaning of it eludes him. 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, and that he will usurp the role of Santa Claus, known to him as "Sandy Claws". He announces that Halloween Town will take over Christmas this year and assigns Christmas-themed jobs, such as singing carols, making presents and building a sleigh pulled by skeletal reindeer, to various residents. Sally (Catherine O'Hara), a rag doll woman who was created by the town's mad scientist Doctor Finkelstein (William Hickey) and has romantic feelings for Jack. Finkelstein keeps Sally locked up except when she knocks him out by slipping deadly nightshade in his soup. Finkelstein knows that Sally is using Nightshade to put him to sleep and escape outside. He believes that Sally is too impatient and that this phase will also pass. Sally has a premonition of Jack's Christmas ending badly. Jack also assigns special tasks to specialized town-folks, which only they can perform. The evil scientist must whip up some reindeer, Halloweentown's top trick-or-treat miscreants are to kidnap Sandy Claws, and Sally's task is to make Jack a red Santa suit. She tries to tell him that co-opting Christmas is a terrible idea, but he's too wrapped up in his enthusiasm to listen. When Sally 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 (Paul Reubens), Shock and Barrel, a trio of mischievous children, to bring Santa (Ed Ivory) to Halloween Town. However, he orders them not to involve their superior Oogie Boogie, a bogeyman with a passion for gambling, in their plot. When he arrives after being kidnapped, Jack tells him of his plan that he will take over Christmas this year, much to Santa's protests. Jack is surprised that he is not the clawed man he expected and orders the trio to keep Santa safe. After this and against Jack's instructions, and largely for their amusement, the trio deliver Santa to Oogie Boogie (Ken Page), 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 and 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, where Zero is seen finishing up reassembling Jack. 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 by going through a tomb. Meanwhile, Sally attempts to free Santa by distracting Oogie, but fails and is also captured by Oogie. Sally claims Jack will free them, but they hear the Mayor (Glenn Shadix) saying Jack is dead. 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 realizes that she was trying to help him because she has very strong 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 where Jack unmasks his deep love for Sally and she returns these feelings for him. They then embrace their new future together and share a very 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.

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