Molly Ringwald as Vivian Ward
Movie: Pretty Woman (1990)
Played by: Julia Roberts
When Ringwald was hot stuff, she had her pick of films. Sadly, that time passed with the end of the 80s, but she once had an early copy of “Pretty Woman.” The role, of course, went to Roberts, but Ringwald could’ve pulled it off. It might have saved her career. On Reddit, she recently said of the choice, “Julia Roberts is what makes that movie. It was her part. Every actor hopes for a part that lets them shine like that.” Somewhere out there, Roberts kissed Judd Nelson in The Breakfast Club and Ringwald played opposite Gere in Pretty Woman.