Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.

An adaptation of the classic, "The Prince and the Pauper" is the retelling of Edward Tudor and young Thomas Canty, two amazing look-alikes caught up in imperial intrigue and scandal. In fleeing from his violent father, Tom stumbles into the palace courtyard, and is seen by young Prince Edward, who takes him in. Each desiring to see what the other's life is like, the boys impulsively switch identities... little knowing what disaster lies ahead at this fault of thought. And soon Thomas becomes a pawn in the hands of Edward's malicious and greedy uncle, who would have the kingdom for himself.

In 1939, boy-wonder Orson Welles leaves New York, where he has succeeded in radio and theater, and, hired by RKO Pictures, moves to Hollywood with the purpose of making his first film.