Tobey Maguire plays David, a nerdy high school student who becomes a main character in the Pleasantville television show.
Reese Witherspoon portrays Jennifer, David's popular and rebellious sister, who finds herself in the Pleasantville world with her brother.
As George Parker, William H. Macy plays the father in the Pleasantville TV family, who undergoes a transformation due to the changes in their world.
Joan Allen portrays Betty Parker, the mother in the Pleasantville TV family who also experiences personal growth as the world around her shifts.
Jeff Daniels plays Mr. Johnson, the soda shop owner in Pleasantville who begins to question the rigid structure of his familiar world.
J.T. Walsh portrays Big Bob, the mayor of Pleasantville who initially opposes the changes happening in the town.
Paul Walker plays Skip, a high school jock in Pleasantville who eventually embraces the newfound colors and changes in their world.
Don Knotts appears as the quirky TV Repairman in Pleasantville who introduces David and Jennifer to the concept of change within their universe.
Marley Shelton plays Margaret Henderson, a character in the Pleasantville TV show who undergoes a significant personal transformation.
Jane Kaczmarek portrays David's Mom, representing the idealized 1950s mother archetype in the Pleasantville TV world.
Giuseppe Andrews plays Howard, a high school student in Pleasantville who grapples with the changes brought by David and Jennifer.
Jenny Lewis portrays Christin, a character in the Pleasantville TV show who experiences newfound emotions and desires in the changing world.
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