The apotheosis of this scenario was his feature directorial debut "Pleasantville" (1998), a Capraesque fable in which two 90s teens find themselves transported into the homogenized, black-and-white world of 50s television. Like the main characters in his previous efforts, the pair both upset and embellish the society in which they find themselves, bringing much-needed change that comes at a price. When Ross naively hit upon the concept of making a movie that began in black-and-white and gradually turned to color (a metaphor for coming alive), he had no idea of the technical expertise required to make it work. 1,700 special effects and $40 million later and after a post-production period spanning more than a year, the finished film opened to generally praiseworthy reviews. For his part, though, the director said, "I'm dying to do a movie that doesn't have any special effects in it. That would be a walk in the park."

It would be five years before Ross would step behind the camera again--although he kept busy with uncredited rewriting chores on films such as "Inspector Gadget" (1999), "Kangaroo Jack" (2003) and "Just Married" (2003)--this time in an attempt to film writer Laura Hillenbrand's bestselling nonfiction book "Seabiscuit" (2003), about the real-life 1920s-era racehorse who became an unlikely champion and an American folk hero of his day. Reteaming with past collaborators Tobey Maguire and William H. Macy as well as top-line performers Jeff Bridges and Chris Cooper, Ross assembled an inspirational, often moving and beautifully photographed version of the historical events, although his desire to capture as much of the book's historical information led to intentionally shorthanded and brisk scenes that often avoided plumbing the characters' genuine emotional depths. The film, however, was rewarded with an Academy Awards nomination as Best Picture as well as a nomination as best Adapted Screenplay for Ross.