9. Halloweentown (October 17, 1998)
Director: Duwayne Dunham
Stars: Kimberly J. Brown, Phillip Van Dyke, Debbie Reynolds, Judith Hoag
Lesson Learned: Generational divides can only be overcome through the supernatural.
If you want to prove to a 20-something the ineptitude of Wikipedia, send them to the page for Halloweentown. Here goes: "Halloweentown is a 1998 Disney Channel Original Movie released in October 1998 to acknowledge the holiday of Halloween." Wikipedia, are you kidding? It was released to acknowledge the holiday of Halloween? It wasn't released to acknowledge the crazy pressure parents put on their children? Or to acknowledge the power of family? Wikipedia, FOH.
Halloweentown spawned three sequels—the money is the motive—but the original stands out as the towering achievement, a film that made the tensions between generations (three of 'em, to be specific) vividly real against the backdrop of a magic land that mostly isn't ripped off from Tim Burton's The Nightmare Before Christmas. Although Debbie Reynolds (who plays the eldest member of the Cromwell clan) has a face that's basically a claymation short. —RS