Billy Madison is a nonworking, noneducated slacker who lives entirely off his dad. He spends his day drinking beer, reading girly magazines, and hanging out by the pool. When his father realizes that Billy is unfit to run the family business, Billy decides that he must go back to school and earn a real education. He figures it will be no problem going back to high school and learning over again, until he learns that his father bought Billys passing grades all the way back in elementary school. Thus, Billy must return to elementary school and pass each grade one at a time in a short time, or else he loses his place as heir to the company. In addition, Billy tries to win the hand of Veronica, a sexy school teacher who thinks her students are more mature than Billy.

A woman suffering from multiple personality disorder tries to piece back together her life.

Madison (Sarah Roemer), a phone sex operator living in New Orleans, is doing everything she can to lead a normal life. When a series of events leaves Madison suicidal and desperate, she locks herself away in her apartment for 30 days. Using a video camera to document herself like a visual journal, Madison vows that if she does not have the answer to her questions and feel more at peace with her life, she will kill herself on the 30th day. Will she be able to piece her life together? Are the people in her life real at all or are they merely figments of her disordered and fragmented mind?