David Wagner (Tobey Maguire) is a Nineties kid with a Fifties addiction. He's hooked on reruns of a classic television show called "Pleasantville," set in a simple place where everyone is swell and perky. David immerses himself in "Pleasantville" as an innocent escape from the trouble-plagued real world that he must share with his ultra-hip, totally popular twin sister, Jennifer (Reese Witherspoon). But one evening, life takes a bizarre twist when a peculiar repairman (Don Knotts) gives him a strange remote control, which zaps David and his sister straight into Pleasantville.
Trapped in a radically different dimension, David and Jennifer find themselves cast as members of the TV family, the Parkers. David has become "Bud" and Jennifer has been transformed into "Mary Sue," and they are surrounded by the black and white suburbia that once kept David glued to the tube for hours. Books have no words, the high school basketball team always wins, and nobody ever questions why things are always so perfect. Initially, David revels in the prozac-like haze that has gripped Pleasantville. But when Jennifer brings her Nineties-like attitude into this unsuspecting era of blandness, things start to happen in living color. All the repressed desires of life in the Fifties begin to boil up through the people of Pleasantville, changing their lives in strange and wonderful ways that none of them had even dared to dream of, until they were visited by two kids from the real world.