Reach the Rock (1998)

Two school kids who are best friends are drinking on the side of a river. One friend bets the other that he can't swim across the river and "Reach The Rock". The friend takes the bet and drowns halfway towards the rock. The entire town blames the the kid for his friends death, he runs away never to be seen again. He eventually comes back to his home town of Shermerville and goes crazy, and starts to trash the town (i.e. breaking store-front windows, stealing a police car). He also meets up with his old high school girlfriend. The majority of the movie takes place in one night.