Repression
While Pleasantville is an idyllic town in many ways, a place where everything is pleasant and no one is ever dissatisfied, its "pleasantness" is held together by repression. The citizens of the town are satisfied precisely because they repress any desire. No one in the town has sex, no one wonders about what is beyond the limits of Pleasantville, and the books are completely without words. As David and Jennifer integrate more into the Pleasantville community, they teach the citizens to let go of their repressive impulses and to access their true desires.
Nostalgia
At the beginning of the film, David is overwhelmed by the modern world, and escapes into the sitcom Pleasantville with a nostalgic sense that things were easier in the past. When he is transported into the show, however, he soon learns that the structures upholding the idyllic life in the town are not actually positive. He learns the difficult lesson that nostalgia isn't necessarily a good thing, and can obscure the more difficult elements of "the way things used to be." Pleasantville may seem perfect, but it is actually a place that suppresses independent thought and artistic expression and subordinates women.
Loneliness & Anxiety
In his real life, David is a rather lonely high schooler. He has one friend, and his only solace is watching reruns of Pleasantville. Early on, we see a montage of David at various classes at school; in each, a teacher talks about the adversity and dangers of the modern world, from global warming to disease. The 1990s are presented as alienating, a time when mounting anxiety only isolates the more sensitive members of society. This anxiety and isolation is what leads David to be so enamored of the world of Pleasantville in the first place.
Listening to your heart
The force that liberates the citizens of Pleasantville from repression and conformity is their ability to listen to their true desires and trust themselves. The characters that turn to color first are those that become sexually active and start to form romantic relationships with one another, but it is not simply sex that ignites people's abilities to listen to themselves. When David encourages George to speak about his feelings for Betty in the courtroom, George turns colorful. Then, when he provokes Big Bob into getting angry, the mayor also turns colorful. All manner of genuine feeling has the power to make the citizens of Pleasantville become colorful. Thus we see that when the characters listen to their true desires, they are delivered from their shallow states of repression and conformity.
Sticking to the script
The citizens of Pleasantville have to stick to a very specific script, as they are not real at all, but characters in a sitcom. The "script" refers both to the synopsis of Pleasantville the show, as well as the social scripts that people subscribe to in a small, conservative society. For instance, Bill does not know how to do his job at the soda shop without David because he has no access to his own independent thoughts, and George nearly short circuits when Betty does not have dinner ready for him on the table after he gets home from work. These scripts seem to make everything in Pleasantville pleasant, but they are also oppressive and limiting, and do not allow for individuals to make their own decisions about their destinies.
Artistic Expression & Culture
Besides sexuality and romance, a major liberating force for the citizens of Pleasantville is an investment in culture and artistic expression. As they begin to turn colorful and follow their own desires, the teenagers of the town get into rock and roll and want to read books from the library that were previously empty. Bill, the owner of the soda shop, is inspired when David gives him a book about art history, and he begins his own painting practice. It is these artistic and cultural endeavors that become most threatening to the community; a mural depicting Betty nude painted onto the side of the soda shop inspires ire among the more conservative members of the community. Art is also the means by which the "colored" members of the community are able to resist most effectively. Even after the code of conduct is introduced to the town, David encourages Bill to paint a colorful mural as an act of rebellion. In Pleasantville, art is a liberating force, something that allows otherwise disempowered people the opportunity to advocate for themselves and resist oppressive restrictions.
Fascism
The Pleasantville government's backlash against the liberation of its citizens is a fascistic one. Mayor Big Bob introduces a list of rules that places huge restrictions on the citizens of the town, forbidding them from having sex, from using the library, and turning "colored" members of the community into second class citizens. The film seeks to expose the ways that conservative "family" values can be hiding a secretly oppressive ideology, one which limits the rights of citizens and places restrictions on human rights.
