This film was designed as a vehicle for Lenny Henry as part of a 3-picture deal the actor signed with the Walt Disney Company, which thought that he had the potential to be a big star in the United States. When this film flopped at the box office, Henry's deal with Disney was canceled, and the other films were never made.
Director Charles Lane cast himself as Duane to ensure that Disney would not fire him during filming.
Screenwriter Andy Breckman got the idea from a popular sketch he wrote for "Saturday Night Live" starring Eddie Murphy. In the sketch, Murphy puts on whiteface and goes out in public to experience what it is like to be a white man.
Director Charles Lane wanted Darnell Williams, who appeared in Lane's previous film, Sidewalk Stories,to play Miles. Disney insisted on Lenny Henry who had signed a contract with them. They set up screen tests for Williams but had no intention of considering him.
Charles Lane made major revisions to Andy Breckman's script. Lane added the ideas of Miles wearing whiteface only to save his own life and being interested in Shakespeare's "Othello". Lane also added the idea of the racist acting teacher which he admitted he borrowed from Robert Townsend's Hollywood Shuffle. Lane got permission from Townsend.