David and Jennifer are twins, but couldn't be more different. While Jennifer is popular and extroverted, David likes to be by himself and fades into the woodwork. One night when they are home alone, they fight over access to the remote control. Jennifer wants to watch MTV with a hot date that's coming over, but David wants to watch his favorite show, a black-and-white show from the 1950s called Pleasantville. In their struggle for the remote, they manage to accidentally destroy it.
Strangely enough, no sooner has the remote control broken than a television repairman is standing on their doorstep offering them a new remote. The teens are confused about how the repairman knew they needed help, but take the remote nonetheless. While once again struggling for control of this new remote, Jennifer and David are transported into the television, suddenly dressed as the young children on Pleasantville. They are even black-and-white.
Jennifer and David do their best to fit in in Pleasantville, with their new television parents, Betty and George, and their various wholesome classmates. While getting to know the world of Pleasantville, they find some peculiarities; people do not have sex, there are only two streets, no one wonders about what's outside Pleasantville, there are no toilets in the bathrooms, and the books have no words.
The changes begin when Jennifer has sex with her boyfriend, Skip. Slowly, the other teenagers in the town begin having sex. From there, people become more and more curious about what is outside Pleasantville. The books fill with words, people learn about art and music, and various objects in the town go from black-and-white to color.
As the changes begin to magnify, David and Jennifer's Pleasantville mother, Betty, begins to stray from her wifely duties. She stops making George his dinner and elects to spend more time with the owner of the local soda shop, Bill, who is an aspiring painter and paints Betty nude.
George and the other black-and-white members of the community are not pleased with these changes and bring their qualms to the mayor, Big Bob. Bob introduces some restrictions in the town that prohibits certain behavior and limits access for people who have become colorful. After Bill and David paint a mural on a wall to resist, they are brought into court. There, David ignites a passion in the mayor so strong that he himself becomes colorful. As a result, the whole town becomes colorful.
Having changed the town for good, David elects to go back to the real world, but Jennifer decides to stay. Back in modern times, David finds his real mother crying in the kitchen about how her life hasn't turned out how she wanted. He assures that there is no one way that life should go, and she feels comforted.
