- Tobey Maguire as David / Bud Parker
- Kevin Connors as the real Bud Parker
- Reese Witherspoon as Jennifer / Mary Sue Parker
- Natalie Ramsey as the real Mary Sue Parker
- Jeff Daniels as Bill Johnson, owner of the malt shop, David/Bud's boss.
- Joan Allen as Betty Parker, Bud and Mary Sue's mother.
- William H. Macy as George Parker, Bud and Mary Sue's father.
- J. T. Walsh as Bob "Big Bob", mayor of Pleasantville.
- Paul Walker as Skip Martin, captain of Pleasantville High's basketball team, Jennifer/Mary Sue's boyfriend.
- Marley Shelton as Margaret Henderson, a pretty and popular Pleasantville High cheerleader, David/Bud's girlfriend.
- Giuseppe Andrews as Howard, David's best friend in the real world.
- Jenny Lewis as Christin, one of Jennifer's friends in the real world.
- Marissa Ribisi as Kimmy, one of Jennifer's friends in the real world.
- Jane Kaczmarek as David and Jennifer's mother
- Don Knotts as TV Repairman
- Denise Dowse as Health Teacher
- David Tom as "Whitey"
- Maggie Lawson as Lisa Anne, one of Mary Sue's best friends.
- Andrea Taylor as Peggy Jane, one of Mary Sue's best friends.
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