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 flop, yet achieved status as a predominant cult film. Later that year, she starred in "Great Balls of Fire!", playing the 13-year-old bride (and cousin) of Jerry Lee Lewis. The film was a box office failure and received divided reviews from critics. Also in 1988, Ryder played in the film, "1969" where she played the character, Beth, the girlfriend of Kiefer Sutherland and sister of Robert Downey, Jr.—protagonists, protesters and flower children against the Vietnam War. In April 1989, she played the title role in the music video for Mojo Nixon's "Debbie Gibson Is Pregnant with My Two-Headed Love Child."