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1
How are David and Jennifer transported into Pleasantville?
At the beginning of the film, David and Jennifer are fighting over control of the remote for the television. David wants to watch reruns of Pleasantville, a sitcom from the 1950s which he loves, while Jennifer only wants to watch MTV with a hot date. When the remote control breaks, a mysterious repairman shows up at the door with a fancy new remote. When David and Jennifer fight over this remote, they get transported into the television show, Pleasantville, taking the places of the two Parker children, Mary Sue and Bud.
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2
What begins the transformation of Pleasantville from black-and-white into color?
When Jennifer begins introducing a more relaxed attitude towards sex to the teenagers in Pleasantville, everything in the town begins to change. As the teenagers begin to pursue their own desires, sexual and otherwise, people and objects begin to become colorful. As the film progresses, we see that it is not simply sexual awakenings that colorize life, but any genuine expression of desire. As the characters begin to accept the uncertainties of life and pursue their curiosities rather than just "sticking to the script," their world becomes more and more colorful.
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3
What does David learn from Pleasantville?
In his real life, David is meek and retiring, and has trouble speaking up for what he wants. He can barely ask a girl out, and so recedes into the idyllic fictions of 1950s sitcoms. When he actually inhabits one of those sitcoms, however, he finds that there are much greater benefits to taking risks than to blending in. After he puts out the fire that starts outside the Parker residence, he becomes something of a town celebrity, and this teaches him that following one's heart and being bold is important. In teaching the citizens of Pleasantville to be more open to spontaneity and uncertainty, David learns these virtues for himself.
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4
Why does Jennifer stay in Pleasantville?
Just as David learns a lesson from Pleasantville, so does his sister, Jennifer. In the 1990s, Jennifer is the quintessential California popular girl, living life in the fast lane and only pursuing superficial markers of status. In Pleasantville, she begins to become more intellectually curious, and opts to pursue her education, eschewing boys and fashion for books. At the end of the film, she chooses to stay in Pleasantville and go to college, as she thinks she has a better chance of the life she wants in the fictional town than in her previous life.
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5
What purpose does art serve in the film, other than as a vehicle for self-expression?
Bill is drawn to art as a mode of expression in the film. After Big Bob and the chamber of commerce introduce a number of oppressive rules, David encourages Bill to use his art for a more politically radical project. He urges Bill to paint a colorful mural (even though those are banned) on the side of a building, depicting the ways that the town's government is tamping down on human rights. His mural shows lovers kissing, and burned works of literature flying up to the heavens with angel wings. By harnessing his artistic powers, Bill creates a monument of resistance, a powerful symbol of the endurance of the human spirit, even under oppressive circumstances.