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 "Sex and Death 101" (2007). The story follows the sexual odysseys of successful businessman Roderick Blank, played by Simon Baker, who receives a mysterious e-mail on the eve of his wedding, listing all of his past and future sex partners. "We will be doing a sequel to "Heathers" next", Ryder stated. "There's "Heathers" in the real world! We have to keep going!" In a more recent interview Ryder was quoted as saying on the speculation of a "Heathers" sequel: "I don't know how much of the movie is official; it's a ways away. But it takes place in Washington and