Billy Madison is the villain
Watching Billy Madison as a kid, of COURSE I thought of him as the hero. He was funny! He had a pool! He hung out with Chris Farley!
But, during a recent rewatch, it’s so clear it’s almost distracting: Billy Madison is the villain. He fails his way through life, slacking off and hanging with his friends. He’s able to be sustained by considerable wealth, because he’s born into it. He contributes nothing to society.
Yet, when time comes for someone to take over the family business, the hard-working employee is passed up for the nepotistic choice of Billy, a man who has no experience, smarts, or etiquette. And the only thing he has to do to secure it is basically get an expedited GED.
Bradley Whitford was absolutely justified to be angry about this decision. A movie from his POV would definitely prove that Billy Madison is, in fact, a villain origin story.