In one of the climactic scenes in Billy Madison, Adam Sandler's titular character is told "What you've just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought. Everyone in this room is now dumber for having listened to it. I award you no points, and may God have mercy on your soul." The entirety of the film in question isn't quite that stupid, but you might be forgiven for thinking that the quote, rather than be directed at Billy, is directed at Billy Madison as a whole.
Directed by Tamra Davis, the film is a vehicle for Sandler to use funny voices, act stupid, and generally play the fool. It is one of those 90 minute films which feels like little more than an extended Saturday Night Live skit, but happily, a relatively funny SNL skit. And in fact, Sandler co-wrote the film with Tim Herlihy with whom Sandler worked at SNL.
The plot has the rich, idle, twentysomething Madison needing to go back to school (starting with first grade) in order to be allowed to take control of his father's hotel empire. We're told that Billy's father, Brian Madison (Darren McGavin), paid off teachers and routinely cheated to get his son through school the first time. Now that the time has come for Brian to retire though, he realizes that Billy is unable to take the company's reins, and instead opts to hand them off to the obviously evil Eric Gordon (Bradley Whitford). In order to get the company, Madison agrees to repeat school, completing a grade every two weeks.
Sandler plays Madison somewhere between a four-year-old and an adolescent, so he fits in perfectly with all the kids around him at school. He even ends up with an inappropriate crush on the "hot teacher," Veronica Vaughn (Bridgette Wilson), who, for perplexing reasons (other than that this is a movie and it therefore has to happen), falls for him too. Apparently all it takes for Vaughn to fall for a student is for him to be the right age and act marginally older than her average student. It doesn't really work as relationship, but the film manages to get away with it because every single scene in the entirety of the movie is absurd, so why not allow an absurd relationship to take place.
Billy Madison is one of those films which has about five or six jokes in it that get repeated over and over again in the film, sometimes hitting better than others. When they do hit, they're strong and will unquestionably cause a chuckle… provided you don't have a strong objection to crude humor. The same sort of formula, but with a (somewhat) better story wrapped around it is used in Happy Gilmore, Herlihy and Sandler's follow-up to Madison.