Dweeby David is eager to stay up and watch the marathon of his favourite golden oldie, Pleasantville. Unfortunately, socially-active twin sister Jennifer also plans to use the television. They fight over the remote and it breaks, summoning a mysterious little fellow (Don Knotts) to their door in a TV repair van. He quizzes David on Pleasantville, and is impressed by his knowledge. He gives him a special remote, and when David and Jennifer fight over it, they are sucked into Pleasantville, where they become Bud and Mary Sue, two black and white teens with a Ward and June Cleaver-esque pair of parents. Bud tries to fit in but Jennifer, confident that "nobody is happy in a poodle skirt" slowly draws the reality of change and desire out of the people of Pleasantville, who slowly begin to turn colour. As Jennifer discovers that she has a serious side as well and David learns he's able to speak out when he has to, leading their "parents" to discover their own inner desires, the conservative mayor tries to fight the changes that he sees happening in his little town, leading to a showdown in the town hall with Bud and the town behind him.

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Jennifer: Hey, can I ask you a question?
David: Sure.
Jennifer: How come I'm still in black and white?
David: What?
Jennifer: I've had, like, ten times as much sex as the rest of these girls, and I still look like this. I mean, they spend, like, an hour in the back seat of some car and all of a sudden they're in Technicolor?
David: I don't know. Maybe it's not just the sex.



When Reese Witherspoon's character is sitting at the desk reading, there is a cheerleading trophy and the cheerleader on it is wearing a mini skirt, - they didn't have mini skirts on the cheerleading outfits then.



In the courtroom scene, all the people that have turned to color have to sit on the upper level. This is reminiscent of "To Kill a Mockingbird" (1963) where, in a similarly-built southern courthouse in the 1930's, all the "colored people" (African Americans) were relegated to the upper level.