Movie: Lean on Me
Sneaker: Nike Air Max 87

Honestly, you could single out any high school drama from 1984 to 1994 and yield screencap gold, but there's an unnatural amount of excellent sneaker sightings on the supposedly impoverished Eastside High School students. Morgan Freeman wandering corridors flanked by Tony 'Candyman' Todd, disarming thugs with a Tannoy and trying to talk Kid Ray out of that bad suit are classic moments, but the jump rope scene, where Joe Clark lightens up, features an Air Max 87 (back when it was an aspirational shoe) in the shot.