Pretty Woman uncomfortable playing a sex worker. Winona Ryder auditioned, but was turned down because Marshall felt she was "too young". Jennifer Connelly was also dismissed for the same reason. Emily Lloyd turned it down as it conflicted with her shooting for the film "Mermaids". Meg Ryan, who was a top choice of Marshall's, turned it down as well. According to a note written by Marshall, Mary Steenburgen was also among the first choices. Diane Lane came very close to being cast (the script was much darker at the time); they had gone as far as costume fittings, but due to scheduling
Winona Ryder (see below). The book "Conversations with Woody Allen" reports that in 2003, film director Woody Allen wanted to cast Robert Downey Jr. and Ryder in his film "Melinda and Melinda", but was unable to do so because "I couldn't get insurance on them ... We couldn't get bonded. The completion bonding companies would not bond the picture unless we could insure them. [...] We were heartbroken because I had worked with Winona before [on "Celebrity"] and thought she was perfect for this and wanted to work with her again." In 2002, Ryder appeared in two movies, filmed before her arrest.