Director Gary Ross's 1998 film Pleasantville tells the story of two teenagers transported back in time to the 1950s, when television comedies portrayed the average American family in an almost surrealistically idealistic light. Anybody familiar with such programs as The Adventures of Ozzie and Harriet, Father Knows Best, and Leave It to Beaver has viewed these depictions of American middle-class existence through a particular prism in which fathers are all-knowing, mothers dutifully perform housework while adorned in their finery, and the social problems afflicting many real-life families are nonexistent. Pleasantville, then, subverts these conventions through the sudden introduction into that era of two modern (circa the late 1990s) teenagers. While one of the teenagers, Jennifer, can be considered the quintessential modern teen, her brother, David, is actually a little more unconventional, obsessed as he is with the world depicted in the 1950s television program with which he has become obsessed, Pleasantville. This program is intended as representative of the actual programs broadcast in television's earliest days, including those listed above.

Pleasantville (the film, not the fictional sitcom that is integral to the film) does contain an existentialist theme. By injecting modernity and realism into the archaic and quaint world of 1950s-era television programming, Ross has forced two different worlds—the one represented by David and Jennifer and the one these two interlopers come to inhabit—to question their underlying assumptions regarding their existence. Note, in the following exchange between the town's mayor, Big Bob, and David, the threat perceived by the former to the entreaties of the latter:

Big Bob: [bangs the gavel] You're out of order!

David: Why am I out of order?

[approaches Big Bob]

Big Bob: Because I'm not gonna let you turn this courtroom into a circus!

David: Well, I don't think it's a circus, and I don't think they do, either.

[David turns to look at the crowd, where many of the black-and-white people are changing into color. There are gasps and murmurs. Jennifer grins]

Big Bob: [bangs the gavel] This behavior must stop at once.

David: But see? That's just the point! It can't stop at once, because it's in you, and you can't stop something that's inside you.

Big Bob: It is not inside me!

David: [amused] Oh, sure it is.

Big Bob: No, it is not!

David has challenged the conventional wisdom and traditions of this idealistic fantasy world, Pleasantville, by pointing out the absurdities inherent in a society in which the problems of the world do not exist or, if they do exist, do not penetrate the invisible borders of this black-and-white world. It is the use of black-and-white photography that illustrates the simplicity of this fictional milieu. The sitcoms of the 1950s predated the introduction of color photography in television. In fact, the television sets of the day were all black-and-white; color programming had to await the development of television sets capable of displaying color images. The phrase "black-and-white," however, is also—and not coincidentally—used to suggest very clear distinctions between right and wrong. There was little room for moral ambiguity and little need of color to illustrate the clear social boundaries in which television depicted American society. The use of color characters intruding on this black-and-white society, then, was intended to inject into the simplicity and idealism of the black-and-white world the realities experienced by viewers in their actual lives.

Pleasantville is an existential experience. The characters' notions of right and wrong are challenged by the vagaries of real life, and they are forced to contemplate their very existence.

One of the most existential elements that come out of the film is the struggle to define reality in complex terms. Life in Pleasantville is a black and white existence.  This is both literal and figurative.  The simplicity that is presented in Pleasantville is challenged with the presence of colors, and divergent ways of thought.  This causes an existential crisis in the citizens of the town as it impacts their state of being in the world and how they interact with this world.  It is also existential because there is little in way of answer.  The ending of the film reflects this, where the husband, wife, and her lover are sitting on the bench and wondering what will happen to them next.  This is highly existential.  No character has "the answer."  No character has a transcendental figure to which they can turn for guidance.  Each character is left to "choose" what is to happen to them, as there is no script, no director, and with the presence of color, only freedom and choice as their companions.  This is highly existential in nature as it allows individuals to get away from "bad faith" and force the issue of choice upon their own in determining their destiny and their identities in the modern setting.