David
David is an introverted teen from the 1990s who escapes from the social alienation of high school by watching old television shows. He has an encyclopedic knowledge of the plots of the classic show Pleasantville, so when he and Jennifer are transported into the show, he knows everything that is supposed to happen. As life begins to change in the town, David encourages the changes and teaches the curious members of the community how to learn more about art and literature and how to listen to their innermost desires, rather than simply conforming to the status quo. He becomes a hero in Pleasantville, finally recognized in a way that he never was in his real modern life.
Jennifer
Jennifer is David's twin sister, and is far more popular than David in their high school. She is promiscuous, shallow, and concerned with status and appearance more than anything. When they are transported into Pleasantville, she is the one who initiates the shift in the environment when she sleeps with her boyfriend, Skip, and it causes color to begin to appear in the town. After a while, she becomes more interested in books and studying than sex, and discovers her intellectual side in Pleasantville in a way that she was never able to in the modern world.
Betty Parker
Betty is married to George in the sitcom world of Pleasantville, mother to Bud and Mary Sue, the characters that David and Jennifer inhabit. As things begin to change in the town, she is drawn towards Bill Johnson, an artistic man in the town. She is one of the only adults in Pleasantville to become colorful, after Jennifer tells her about masturbation and she begins an affair with Bill. Inspired by her children, she wants to break out of her conformist and subservient position in her own house.
Bill Johnson
Bill is the owner of a local soda shop in Pleasantville, and David's boss. He's a by-the-book kind of guy who works hard, but he begins to take an interest in painting when David shows him a book from the library on art. This opens him up to the power of self expression and he begins painting a great deal, eventually painting a nude of Betty Parker onto the window of the soda shop that causes a huge controversy in the town.
Big Bob
Big Bob is the mayor of Pleasantville. He is a conservative man who just wants everything to stay the same, hoping that everyone will stay black-and-white and that he can maintain the status quo for as long as possible.
George Parker
George is David and Jennifer's father in Pleasantville. He is an affable and good-natured man, but he becomes upset when Betty starts going after her own desires. He is frustrated not to have a doting wife at home, and longs to be taken care of by the woman he loves.
Margaret
Margaret is David's girlfriend in Pleasantville. While the script of the sitcom dictates that she is supposed to go steady with Whitey, she chooses David instead after he expertly teaches the local firefighters how to put out a fire.
