Corrected entry: David and Jennifer transfer themselves to Pleasantville without any belongings apart from the remote control. Since there has never been rain in Pleasantville, the umbrella the "Bud" gave his girlfriend when standing outside could only be David's school prop, from "outside" Pleasantville.
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Correction: They never had a fire, but they had a fire department and a truck with hoses, and hydrants, and protective gear. They even called it the Fire Department, not the Cat Rescue Department. They have books with nothing written in them. There's no reason umbrellas can't exist in Pleasantville.
K.C. Sierra