Near the beginning of the film, Jonathan Brandis' character Matthew calls Rodney Dangerfield's character Chester, "Chesterfield." Brandis had a habit in real-life of referring to certain friends in jest by adding "field" to the end of their names. It is rumored by some who knew him that he carried this over into the film and ad-libbed "Chesterfield" as an inside joke.
The movie was originally going to film in Dallas, Texas but the location was changed to Denver, Colorado because of concerns about the effects of heat stress on child actors in Texas.
Whoopi Goldberg was given the option to either portray Julie in this movie or to take the lead role in Sister Act - Eine himmlische Karriere (1992). Although Goldberg loved Rodney Dangerfield and considered him a comedy icon, she chose the latter film because she felt it would be more successful. She proved right as Sister Act - Eine himmlische Karriere (1992) turned out to be one of the top 10 grossing films of 1992, while Monty - Immer hart am Ball (1992) flopped at the box office.
Originally, the production wanted Matthew, when he was in disguise as Martha, in heels. For practice, Jonathan Brandis had to walk in them for some time, later commenting "high heels are horrendous." For filming, however, it was decided to go with flats because they wanted Martha to "be as awkward as a girl."