Everyone thinks of Pretty in Pink as John Hughes' second film with Molly Ringwald, but most people forget that Hughes only wrote and co-produced the script. It was Howard Deutch that directed the complicated love triangle between poor kid Andie (Ringwald), rich kid Blane (Andrew McCarthy), and Andie’s devoted lifelong friend, Duckie (Jon Cryer). Whether you were Team Blane or Team Duckie, Andie became the avatar for every underappreciated kid who felt the societal pressures of high school life. – Richard Whittaker