In the hands of another writer, this movie could have been made as just a parody of 1950's sitcoms like "Leave It To Beaver" or "Ozzie and Harriet." But this film isn't about how clichéd those series look decades later. It's about the false nostalgia for a past that never existed. We survived the past and we know that everything turned out all right. Because of this, we selectively choose our memories and weed out the unpleasant ones. That's why the past is sometimes seen as "the good ol' days." Pleasantville does not represent how the 50's actually were but rather an idealization of what people THINK the 50's were---no one had sex, everyone got along swell, and life was fairly easy. Nothing could be further from the truth, and there are many film from that era which show how real people (even in suburbia) actually lived. This film argues that free will and choice is ESSENTIAL to life and that we should embrace freedom instead of fearing it. It isn't just about making out, but having the OPTION to make out.
Another reviewer claimed that this film was an attack on the 50's, but David and Jennifer could very easily have been dumped in the world of "The Brady Bunch", "Gilligan's Island" , or "Batman." But setting "Pleasantville" in a 1950's sitcom allows for the brilliant metaphor of black and white versus color. Black and white photography is a stylized depiction of the universe, but unless you're color blind it's not the way you actually see the universe. When we first see Pleasantville's citizens, all of them are cardboard cut-outs of stereotypes. As they begin to open up and become real people, color seeps into their world. The catalyst seems to be the willingness to experience new sensations and become vulnerable. Jennifer has slept with lot of guys when she was in the normal world, so sex does not change HER into a color character. On the other hand, when she actually finishes a book (without pictures) for the first time in her life, THEN she becomes colorized. Similarly, David does not bloom into color until he breaks out of his aloofness and defends his "mother." Compare the way he ignores his real mother at the beginning of the film to how he consoles and comforts her at the end to see how much David has changed.
I could go on and on, but I think you get the idea. There are a lot of films out there that are very entertaining and/or very moving--like "Raiders of the Lost Ark" or "Titanic." Movies like "Pleasantville" which challenge the audience and force them to think are very rare, and should be treasured by the discerning filmgoer.