Watch Movies2Watch. My Old School centered on the Stephen Mailer character as he began his first year of college in the early 1970's. Mailer played a young man who is trying to deal with the transition into college, the complications of co-ed dorm life (Carla Gugino played a possible love interest), getting to know his dorm-mates (Fraser, Saxton, and others), and the fine line of being (mis)lead by faculty who seduced and (de)graded him. It was essentially "The Wonder Years" grows up and goes to college.