How others will see it. A lot of people will watch this film, and halfway through "realize" they are watching something important, or at least meaningful. They won't be able to cogently express what the meaning is, however.
Trying to figure out the message of the movie constitutes its primary entertainment value. More about this later. Young cute guy Tobey Maguire gets most of the screen time, so there's eye candy, at least for the women. Reese Witherspoon has a decent-sized supporting role, but she's not onscreen enough to encourage corresponding male interest.
How I felt about it. Clearly, Pleasantville is trying to say something. There is, in fact, a jumble of character and culture transformations. What are they, what do they mean, are they significant, are they effective? Since the editing is superlative and the Hollywood sheen is fully present, the quality of the film rests on the success of its message. Whatever that is.
Let's start with what can be understood easily, then move on the more complex questions. There are five major character transformations: three belong to Maguire, Witherspoon, and their television mom, Joan Allen. The town has two transformations, into polarized enlightened and conservative factions.
Allen changes from a Stepford wife into a woman liberated from the restraints of monogamy and conformity (Yawn). A similar enlightenment, of a sexual and artistic nature, affects a portion of the town. The rest of the town is afraid to adapt, and reacts by suppressing the rebellion. This cultural rivalry vaguely resembles Nazi Germany, with its prejudice, book-burning, vandalism, etc.
These factions seem irreconciliable, but they're not. How does this happen? As I understand it, the mayor gets mad, and Joan Allen's husband admits she's pretty in color. Nothing here is at all extraordinary. Your character and abilities, and not your emotions, make you a better person.
Witherspoon changes from a deeply cynical and sexually active snob sister into a bookworm who eschews boys altogether. Huh?
Maguire changes from a clever but minor nerd into the leader of the town's ever-growing enlightened faction. He also gets a perfect 10 girlfriend who worships him. Yet he wants to leave this environment to return to a world where he's nothing, while Witherspoon wants to stay behind. Earth to Witherspoon: D.H. Lawrence books exist in the present, too. And no, Maguire's character is unlikely to have read them during commercial breaks for "Pleasantville" reruns.