Who was Billy’s Mother?
I have a somewhat dark theory I concocted after a recent viewing of Billy Madison. In the film, I don’t believe his mother is ever referenced or addressed. This led me to believe that it is entirely possible that she had died. Let’s explore what this would mean story-wise and thematic.
The crux of Billy’s journey is the death of his mother at a young age. Obviously, this would have a huge impact on a young child. However, Billy’s father, either intentionally or unintentionally, neglected to address Billy’s grief and possibly his own.
Billy went back to school without any sort of coping or any emotional support from his father. Likely unable to focus on academics and struggling emotionally, Billy develops a learning disability and begins to act out. He is not interested in learning at this point, he wants to feel better. He’s tired of being sad and wants to be a happy, normal kid. His grades suffer and decline, but he is having fun with his classmates and being a class clown. He enjoyed the laughter and the attention. His academic challenges are not due to a lack of effort, but rather an overwhelming struggle to cope with his grief and trauma.

Billy’s Arrested Development
Billy, unfortunately, wasn’t being parented. His father focuses on the business and his work. He doesn’t address his grief with Billy and doesn’t talk about it. When Billy’s dad learns that he is failing in school, instead of intervening or getting him help, he pays off the school to give him passing grades, unbeknownst to Billy.
This action allowed Billy to continue these behaviors without any repercussions for several years of his most formative years. By high school, he is in full party mode and is passing all of his classes without trying. Billy doesn’t have a care in the world and is just enjoying himself. After graduating, Billy stays the same. He’s partying all day everyday while his peers are growing into their adult selves, starting careers and families.
Billy begins to lose more and more friends due to his immaturity and inability to grow up, and eventually is left with only 2. They appear to just be Billy’s groupies who get to hang out in a mansion with a pool all day and getting wasted. This is the first part of the film where we meet adult Billy Madison. Drunk in his father’s pool, driving a golf cart over the gardeners beautiful arrangements they spent time and effort working in a rush to get his nude magazines, and hallucinating a giant penguin.

He is a screw-up and a disappointment. His father, however, still holds out hope that Billy will grow up and take over the family business. But during an embarrassing dinner in front of all his work colleagues, Billy’s father has had enough and nearly gives up on him. He tells Billy he’s going to turn this business over to someone else when he retires.
This is one of the first signs of initiative Billy shows as an adult, because he finally had something to lose. He also had something to prove. To himself, his father, and his peers.
The Plot
We begin the overall plot of the film with Billy doing a school gauntlet challenge from kindergarten all the way to 12th grade. If he passes, he will have proven to his dad he is responsible and can take over the family business.
This plot device sort of serves as therapy for Billy. Going through this process teaches him social skills, life skills, and basic understanding. Each grade teaches him something and gives him the tools he needs to grow up and be his own person.
In Kindergarten, he learns respect and responsibility (you have got to get out there and find that dog, ya know?). In 1st grade, he learns about following through on tasks and that success requires concentration and effort, not just fun and games. By the 2nd grade, Billy learns about cooperation and teamwork. He begins to understand the value of helping others and being part of a community.
Once in 3rd grade, he is grasping the importance of good study habits and how to manage his time better. He sees the value in preparing for tests and assignments. By 4th grade, he is starting to gain a sense of independence, showing signs of maturity. And when he reaches 5th grade, he is getting a better understanding of compassion and empathy, he starts to form real friendships and begins to understand the value of kindness.
Covering 6th-12th grade since a lot of it is glossed over. But this is the era when he starts taking on more complex assignments, learns about long-term consequences, and begins to understand the importance of setting goals and thinking about the future. By this point, Billy is shaping into a mature and responsible adult.

Consequences & Outcomes
The school gauntlet ends up saving Billy’s life in multiple ways. Had he not called an old classmate of his, who he treated very poorly, and apologized, he would have been assassinated at some point in his life. This action also unintentionally saves him from being shot by Eric in the 3rd act of the movie.
If he hadn’t gone through with this gauntlet, he would likely have drank himself to death. If his father hadn’t presented a consequence for Billy for his lack of maturity and direction, he would’ve wasted away in his dads pool, forever floating in mediocrity.
Look, I’m dissecting an Adam Sandler comedy from 1995. I very much doubt this was the intention of the screenwriters. But I feel that it gives added context and a deeper motivation and understanding of the Billy Madison character. Why he was the way that he was, and he grew as a person and character. Not just in academics, but in all aspects of his life.
He transforms from an immature, self-absorbed man into someone capable of taking on real-world challenges. The film also instills the importance of being responsible, respectful, disciplined, empathetic, and mature. It’s refreshing to see a film about someone who wants to be better and puts in the effort to do so.
Chris Farley has a great cameo in it too. You can watch just for that.

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