Robert Altman felt that Liv Tyler had been too glamorous in previous films, so he asked her to cut her hair short for for this movie.
Anne Rapp's association with Robert Altman began when she met him through her ex-husband who was one of Altman's racetrack buddies. The two clicked and started writing scripts together. Their first collaboration was one of the segments for the "Gun" (1997) mini-series. This was their second and they both enjoyed the experience so much that they reunited the following year for "Dr T and the Women".
Frances McDormand and Anjelica Huston were both originally cast in the film, but they eventually dropped out.