Cast and Crew: Gedde Wantanabe, Anthony Michael Hall, Paul Dooley, John Cusack, Joan Cusack, Brian Doyle-Murray, Jami Gertz, Zelda Rubenstein
What It’s About: Samantha Baker (Molly Ringwald) attempts to navigate her sixteenth birthday’s many challenges, including her family forgetting all about it in the wake of her sister’s (Blanche Baker) wedding.
Why Watch it Today?: Illinois Territory was created on this date in 1809. John Hughes made a cottage industry out of youth oriented films set in Chicago and its suburbs in the 1980s, finding many a star (today’s film plays like a game of “spot the soon to be famous actor”) in the process.