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 loosely connected to the Roman Catholic Church and determined to prevent Armageddon in "Lost Souls" (2000), which was a commercial failure. Ryder refused to do commercial promotion for the film. Later in 2000, she was one of several celebrities who made small cameo appearances in "Zoolander" (released in 2001). On October 6, 2000, Ryder received her own star on the Hollywood Walk of Fame, located directly in front of the Johnny Grant building next to the Hollywood Roosevelt Hotel on Hollywood Boulevard. She was the 2,165th recipient of this honor. Ryder had a hiatus after her shoplifting incident in 2001