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Billy Madison deciding which is actually better

Growing up, Billy Madison was one of my favorite movies. Straight up, I’ve seen this movie at least 50 times since I was first introduced to Adam Sandler’s lovable man-child at a friend’s house in the second grade. The movie, while technically a PG-13 comedy that I was probably too young to be watching, resonated with the young 7-year-old version of myself that hadn’t really seen anything like it before. And over the years, I’ve continued to watch it on every format including VHS, on cable (with the extra kickball sequence), on DVD, and streaming (like I did for this piece), and it’s gotten to the point where I can pretty much quote the whole movie.

Over the years, I have graduated from high school and college, started my career, got married, and had a few kids, and during that time, I’ve started to ask myself some pretty big questions regarding a mid-90s comedy about a 27-year-old moron going through the public school system in order to gain control of a Fortune 500 hotel chain. While some people toss and turn at night questioning the choices they’ve made in life, I’m over here wondering how a public school system allowed an adult to register for classes, why isn’t Eric Gordon in jail (or an insane asylum), and why are we rooting for Billy Madison in the first place.

Well, just like how Billy was given the opportunity to go back to the first grade as a fully grown adult, I too have been given the chance to ask the most serious questions we’ve all wanted to ask about a not-so-highly-regarded comedy from 1995.

Veronica Vaughn and Billy Madison in his tent

How Does Anyone At Billy’s School Still Have A Job?

Throughout the film, we spend most of our time at Billy’s various schools, with the majority of classroom scenes taking place in the elementary school where we meet Veronica Vaughn (Bridgette Wilson) and Principal Max Anderson (Josh Mostel). We’ll start with Anderson because his offenses are just so insane that I can’t even wrap my brain around it. For starters, he killed a guy. I know, I know, it was an accident during a wrestling match 10 years before the movie is set to take place, but what is someone who probably has a manslaughter charge doing running a public school. I don’t want to sound like Eric Gordon here, but how did Anderson have time get certified when he was parading around as “The Revolting Blob” in the first place?

The other thing that doesn’t look good for Anderson is the whole valentine to Billy. I get it, they’re two adults and they can do as they wish, but on the other hand, Billy is a student, and that’s a big no-no in the school system. But Anderson isn’t the only school employee who crosses that line with Billy during the movie, as the one and only Veronica Vaughn broke the cardinal rule of teaching - she started a relationship with her student. Yeah, he was no longer a student in her class when they started dating, but he was about to enter the fourth grade when they shared their first moment in Billy’s elaborate tent. It’s one of those things where it’s better to just not think about it.

Billy Madison trying to figure this all out

How Is Any Of This Even Legal?

In all seriousness, how is anything in this movie legal in the first place? I know it’s a movie, and a dumb one at that, but in the first 10 minutes of Billy Madison, Billy’s dad, Brian Madison (Darren McGavin) admits to paying his son’s way through school the first time around just before he agrees to let him go through the public school system again in order to take control of his hotel empire. In the real world, that’s called bribery, which is a crime, but let's look beyond that.

The bribing on Brian Madison’s part is one thing, but a school allowing a 27-year-old man to spend two weeks in each grade over the course of school year is totally different issue. Not only does it set a precedent that anyone can blow through elementary, junior high, and high school with only having to do things like pass a spelling bee or pass an academic decathlon in order to graduate, it also should result in people losing their jobs for allowing this farce to go on in the first place.

Ernie and Billy calling Ms. Vaughn

Wouldn’t Billy’s Friends’ Parents Be Freaked Out About Their Kids Hanging Out With An Adult?

As Billy works his way through the public school system in hopes of taking over his dad’s company, Billy forms friendships with students along the way. Over time, Billy spends less time with Frank (Norm Macdonald) and Jack (Mark Beltzman), and instead starts hanging out with his fellow students, especially Ernie (Jared Cook). It’s understandable, Billy is going to school with these kids all day, so he’s bound to become friends with some of them. That’s all fine and all, but don’t you think Ernie’s parents would be freaked out to find out that their son is hanging out with a 27-year-old drunk idiot who chases around an imaginary penguin around his father’s estate?

Eric Gordon should be in jail for this

How Is Eric Not In Jail After Pulling A Gun On Billy?

Near the end of the movie, Eric (Bradley Whitford) has a chance to beat Billy in the academic decathlon after Billy tires and fails to compare the Industrial Revolution to The Puppy Who Lost His Way, but is given a question on business ethics. He tries to answer, but ends up freaking out and pulling out a revolver that he then points at Billy. Principal Anderson (in his full wrestling attire) runs in and saves the day, but Eric is able to recover and this time points his gun at and tries to shoot Veronica Vaughn before getting shot by Danny McGrath (Steve Buscemi).

You would think that Eric would be carted off to jail after the incident, or at least fired from the company, but nope, he's sitting there at Billy's graduation as if nothing happened. In a movie where the entire O'Doyle family got theirs and died in a horrific car crash (while still yelling "O'Doyle Rules') after they spent the entire movie bullying Billy at every corner, nothing happens to the weaselly, antagonistic Eric Gordon, and that just doesn't sit right with me. How he didn’t get arrested for bringing a loaded weapon into a school is something that I’ll never understand.

Billy Madison performing his redemption song

Is Billy Better Prepared To Run The Business?

I get it, the whole point of the movie was for Billy to go back to school, but how will any of what he learned throughout the movie help him run a Fortune 500 business after his dad hands it over to him upon graduation? The highlights of Billy's educational journey include him drawing a blue duck, spelling the world "couch," writing in cursive (poorly, I might add), and winning the academic decathlon on a technicality. Through all of that, it seems like Billy's "education" would be better used in a trivia match than in a large company that operates hundreds of hotels across the world.

Those are just a few of the things about Billy Madison that don’t make a lot of sense when you think about them, which are all things you really shouldn't think about too much. Now, the only thing that needs to be answered is if the clown who fell at Billy’s birthday party was unconscious in Billy’s yard the whole time or was he up to something else.