Life is hard and, for a decade, nobody did angst like John Hughes. In the mid-'80s, the writer-director began his career tackling the tough issues of the teen years: Dateless geeks, star athletes with daddy issues, all-day detention. But like most people, as he got older, Hughes put all that adolescent angst behind him and while the consequences for his characters got more dire, they also stopped taking themselves so seriously.

Pretty in Pink, Andrew McCarthy, Molly Ringwald, Jon Cryer, 1986. © Paramount. Photo courtesy of the Everett Collection.