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 was in the family comedy-drama "Mermaids" (1990), which co-starred Cher, Bob Hoskins and Christina Ricci. "Mermaids" was a moderate box office success and was embraced critically. Ryder's performance was acclaimed; critic Roger Ebert of the "Chicago Sun-Times" wrote: "Winona Ryder, in another of her alienated outsider roles, generates real charisma." For her performance, Ryder received a Golden Globe Award nomination for Best Actress in a Supporting Role. Ryder then performed alongside Cher and Christina Ricci in the video for "The Shoop Shoop Song", the theme from "Mermaids". Following "Mermaids", she had the lead role in "Welcome Home, Roxy Carmichael", a