Rysher Entertainment had tried selling the film to various studios including Paramount Pictures, New Line Cinema, MGM and TriStar Pictures. But all three studios turned it down. Warner Bros picked up the theatrical and home video rights to the movie as they had a deal with the Olsen Twins' production company Dualstar Productions.
The first draft of the script by Deborah Dean Davis was never read by Director Andy Tennant. Jeff Schechter's draft made this a "go" picture with Rysher Entertainment. Tennant was hired, and offered help for the movie's problems. He and his writing partner Rick Parks re-wrote Schecter's draft. Tennant and Parks were re-written by Producer Jim Cruickshank. The studio preferred Tennant and Parks' draft with notes, so Tennant and Parks took another pass. The WGA ruled against any other writer's credits due to biased bylaws, which disallowed writers or directors with partners from receiving credit on features unless in extreme circumstances. None of Davis' dialogue was used.
Steve Martin, Kurt Russell, Tim Matheson, Rick Moranis, Pierce Brosnan, Dan Aykroyd, Robin Williams, Tom Selleck, Mel Gibson, Jeff Goldblum, Tom Hanks, Dennis Quaid, Martin Short, John Travolta, Dylan McDermott, Griffin Dunne, Hugh Grant, Chevy Chase, Sam Neill, Michael Keaton, Richard Dreyfuss and Bill Murray were all considered for the role of Roger Callaway.
Winona Ryder was director Andy Tennant's first choice for the role of Diane Burrows. Rysher Entertainment rejected Ryder because they thought she was too young for the role. Geena Davis, Sandra Bullock, Laura Dern, Joan Cusack, Sigourney Weaver, Elizabeth Perkins, Goldie Hawn, Nicole Kidman, Linda Hamilton, Julia Roberts, Catherine O'Hara and Julianne Moore were also considered for the role.
When Amanda is first mistaken for her twin sister at the Callaway house, she refers to Vincenzo as "Lurch". This is a reference to The Addams Family (1964) with Lurch being the name of the tall, scary butler.