2. Pleasantville - David
It might not be a substantial role particularly, in terms of the challenges presented by the character, but Maguire is as natural a fit as you're likely to see in Pleasantville. The film is a wonderful charmer, written by the mind behind Big and the under-loved Dave, and based on an irresistible high concept that sees two modern teenagers unwittingly transported into the prim, desexualised world of a black and white sitcom. The culture shock works well, but it's the integration of Maguire's character that really sells it, as he finds himself oddly at home with the stricter rules of his new residence. That of course leads to conflict with his on-screen sister Reese Witherspoon, who is also excellent, and in truth, though the character creations within Pleasantville are engaging, the film's success rides entirely on the performances of the central sibling pair.