David (Tobey Maguire) is the classic high-school nobody, with divorced parents, both self-involved, and a twin sister, Jennifer (Reese Witherspoon), on the road to slutsville. Faced with all of today's social ills, he focuses is attention on reruns of a 1950's sitcom, all but memorizing each episode. He compares the pain and loneliness of his own life with the perfect existence of the Parker family, and yearns for a time where everyone had a place and everything went according to the rules.
Enter a rather peculiar fairy godfather (Don Knotts), who gives David a strange, clunky TV remote that suddenly transports brother and sister into the monochrome world of "Pleasantville," where they take the place of Bud and Mary Sue Parker.
It turns out to be not-so-Pleasantville. Books are as blank as the minds that "read" them, and the town's main street goes nowhere but back to its own beginning. The fire department does nothing except rescue cats from trees, and basketball shots never miss the rim. Restroom stalls are empty and everybody smiles enough to make the viewer's face hurt.
David, an expert on what-comes-next, is inclined to keep to the script. Still, it is he who introduces the first discordance into the boilerplate world of Pleasantville when, fearful of the results, he tries to dissuade the school basketball star, Skip (Paul Walker) from dating "Mary Sue." For the first time in history, Skip tosses the ball and it spins around the rim - and bounces out.
True to "Bud's" fears, "Mary Sue" quickly teaches Skip the joys of a new sport - submarine racing. On the way home afterwards, he glances at a rose bush and sees a single red rose.
That first crack in the black and white simplicity of Pleasantville increases geometrically as Skip passes along his new knowledge to his friends and David's "boss," Bill Johnson (Jeff Daniels) gives up the rigid routine of the script and discovers art. Bit by bit, color spreads throughout the town, to the delight of the caged who hadn't been aware of the bars and the dismay of those who found those bars comforting. These video Babbitts draw up a Code of Conduct forbidding the use of color, which leads to a clash between those willing to explore their inner landscapes and those afraid of what they might find there.
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