The plot of Billy Madison revolves around "Billy Madison", a 27-year-old heir to his wealthy father's chain of hotels (Madison Hotels). Billy's father Brian (played by Darren McGavin) is losing confidence in Billy. Billy must prove that he has what it takes to run the Madison Hotels empire and, as part of an agreement with his father, heads back to school to obtain his high school diploma. In order to gain the trust from his father, Billy must pass all grades within 24-weeks (grades 1-12, two grades per week).
While in school, Billy becomes attracted to a teacher, Veronica Vaughn (played by Bridgette Wilson). At first Veronica wants nothing to do with Billy, but over the course of several weeks, she warms up to him. Veronica helps Billy study, but Billy comes to hate school and reverts back to his old ways of being a slacker (skipping school, drinking all day, etc..). Because of this Billy's father Brian decides to give the company to his associate Eric. Not being satisfied with this, Billy declares that an academic decathlon should take place with the winner receiving control of Madison Hotels. Billy and Eric are tied heading into the last event of the decathlon. Can Billy pull it off and take control of his father's company? Or will Eric, the business associate with ulterior motives, gain control?
Other notable cast include appearances by Norm McDonald, and Josh Mostel. Chris Farley also makes an uncredited appearance as the bus driver for a class field trip.
Billy Madison has a run time of 89 minutes and is rated PG-13 (for language and crude humor).
Some people just never grow up. Know the type?
That's exactly what this movie about, a man who refuses to grow up, that is until he is about to lose possession of his father's billion dollar company if he doesn't pass school and get his high school diploma.
So Billy Madison does what he has to and goes back to school starting with kindergarten. He spends 2 weeks in each grade and has to pass to move on to the next grade and so on.