Every single thing that starts to happen in Pleasantville was actually happening in the 50s. Pre-marital sex. Brubeck. The Civil Rights movement. The visual art. Proto-feminism. All of it.
The real message of this movie is that the TV show version of the 50s was the fake. "Leave it to Beaver" and "Ozzie and Harriet" were not "historical documents." They were themselves conservative reactions against the underlying currents of change.
The women who played the stay at home moms in those shows (e.g. Barbara Billingsley) were THEMSELVES WORKING MOMS! While they were making us think that the stay at home mom was both descriptively accurate and the proper aspiration, they had to figure out who was going to take care of their kids.
The actual 50s were not the fictional 50s of the TV shows of the time. It's the anti-nostalgia of "Pleasantville" that makes it brilliant. The real 50s was much more like the all-color version of Pleasantville, not the imagined perfection of TV shows or of David's fandom.
And there are so many beautiful scenes in this movie as the Pleasantville characters discover that they are just as human as we've always been, and still are. But Tobey McGuire doing Joan Allen's make-up to get her back to black-and-white is perhaps the most powerful. As a metaphor for the ways in which perceptions and portrayals of what womanhood should be clashed with the reality of life in the 50s, it just doesn't get better than that.
We have very much painted over the much more interesting and beautiful and complex world of the 50s thanks to our TV-driven nostalgia.