One of John Hughes' most popular and well-known coming-of-age films, Pretty in Pink remains a fan favorite to this day. Unpopular, working class teenager Andie (played by Molly Ringwald) finds herself having to choose between her longtime awkward friend Duckie and the rich, preppy Blane (played by Jon Cryer and Andrew McCarthy, respectively).
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The role of Andie was written for Molly Ringwald but she didn't accept it at first. Other actresses that were considered were Lori Loughlin, Sarah Jesica Parker, and Brooke Shields before Ringwald chose to be onboard.