The film follows the misadventures of Jack Skellington, Halloweentown’s beloved pumpkin king, who has become bored with the same annual routine of frightening people in the “real world.” When Jack accidentally stumbles on Christmastown, all bright colors and warm spirits, he gets a new lease on life. He plots to bring Christmas under his control by kidnapping Santa Claus and taking over the role. But Jack soon discovers even the best-laid plans of mice and skeleton men can go seriously awry.
Teen misfits Gary (Anthony Michael Hall) and Wyatt (Ilan Mitchell-Smith) design their ideal woman on a computer, and a freak electrical accident brings her to life in the form of the lovely, superhuman Lisa (Kelly LeBrock). She outfits Gary and Wyatt in cool clothes, surprises them with a Porsche and helps them stand up to jerks Ian (Robert Downey Jr.) and Max (Robert Rusler). But, all the while, the boys must hide Lisa’s existence from Chet (Bill Paxton), Wyatt’s nightmare of a big brother.