I saw Free Willy 2 in 6th grade at least 7 times...and enver saw the end. Everytime the teacher would put it on, she'd start it over.
Pay it Forward makes the list, Stand and Deliver as Well. Romeo and Juliet from the '60s as well as the Dicaprio version a few years later. The Scarlet Letter, a version that was like a play or soemthing, was really terrible as well.
On the plus side, we did watch Spider-man, the first two Jurassic Park films, and when the football team went to state, those of us who didn't give a **** about the team went to school like any normal day. But since most teachers were gone, we split into groups and went to different class rooms with the few teachers we had. I brought movies with me and a portable DVD player. We hooked it up to the Tv and ended up watching Night of the Living Dead, followed by the parody Night of the Living Bread. Ah, good times.