Terry Gilliam tested more than half a dozen actresses to play the part of Jill Layton, interviewing or testing Rosanna Arquette, Ellen Barkin, Jamie Lee Curtis, Rebecca De Mornay, Rae Dawn Chong, Kelly McGillis, Joanna Pacula, Michelle Pfeiffer, Kathleen Turner, and he even considered Madonna. Gilliam's personal favorite was Barkin because he thought she had a great combination of sex appeal and toughness that would work for the character. He stated later that while Kim Greist gave an excellent audition and his close circle of friends and family advisors liked her, he mainly picked her for the role because she had only one movie credit to that date (C.H.U.D. (1984)), and this would enable her to create a truly original character for audiences without any prior expectations. He also said that working with Greist, who was difficult on set, and whose material had to be severely reduced to help the movie, drove home that "experience really does count for something."

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