Released in 1986, this John Hughes comedy follows a quick-witted teen who engineers an audacious break from routine, pulling his best friend and girlfriend into a whirlwind urban adventure that nudges a reluctant soul toward self-belief.

Alan Ruck plays the tightly wound friend whose quiet crisis becomes the film’s emotional core. He later earned acclaim in Spin City and Succession, and was 29 while portraying a high school senior.