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 comeback playing leading roles. The film instead became the "welcome-to-Hollywood coronation" for Jolie, who won the Academy Award for Best Supporting Actress for her performance. Jolie thanked Ryder in her acceptance speech. The same year, Ryder was parodied in "". The following year, she starred in the melodrama "Autumn in New York", alongside Richard Gere. The film revolves around a relationship between an older man (Gere) and a younger woman (Ryder). "Autumn in New York" received mixed reviews, but was a commercial success, grossing $90 million at the worldwide box office. Ryder then played a nun of a secret society