Believe it or not, there was once a time when Adam Sandler was considered the creme of the crop when it came to goofy comedies. Nowadays, we've pretty well outgrown him as the goofball, and thanking the Good Lord he's moved onto some serious acting. But at one point in time, he was pretty well neck-and-neck with Jim Carrey for who the better comedian was. 'Ace Ventura' came out in 1994, one year before this one, and each was respectively their big breakout film (at least from my perspective).
Those who know me well know that I have a big soft spot for this movie. I remember seeing it in the theater upon its release when I was 12, and to this day, it may take the cake for the most I've ever laughed during a film. It was here that I found my fondness for what can only be described as completely random comedy. The whole time, I'm laughing my ass off, but at the same time going "this is so stupid!" To this day, it remains one of my favorite comedies, and something I like to throw on for a good laugh, or to cheer me up. This is one of those great Rotten Tomato dividers, where the critics give it a 40% but audiences give it a 79%, and I fully side with the audience.
The film centers on Billy Madison (Adam Sandler); smart aleck son of the wealthy owner of Madison Hotels, Brian Madison (Darren McGavin). One day Brian has a talk with his son about handing the company over to Eric Gordon (Bradley Whitford) who is a BAD, BAD MAN! Billy is about to miss out on inheriting the company due to his slacking, childlike nature, and the fact that he only graduated because his father paid the teachers to give him decent grades. But the idea of Eric getting the company provokes some seriousness within Billy. He agrees with his Dad that if he can do first grade through twelfth grade all over again, do each grade in two weeks, take the tests, re-graduate, and proove to him that he's not an idiot, he gets to take over Madison Hotels.
In truth, it doesn't make much sense that he's able to do what he does in the movie and physically go back to the first grade, and try to see it through to the end. The idea of a grown man in a classroom full of kids who says he's there to be educated can only come across as creepy and weird today, and as something that could probably never happen. The idea here seems to be that his Dad is just that rich - you throw money at anything, and it'll work out in your favor. But for as odd as it all sounds, it really makes for some of the best comedy in the movie. His interactions with these kids are more likened to him being everyone's crazy, fun "Uncle Billy".
Once Billy gets to third grade, he meets his teacher Ms. Veronica Vaughn (Bridgette Wilson), who becomes Billy's love interest through the movie, and she's a pretty good example of a strong female character from the mid-90s. She comes along and helps Billy focus on what's important, and some of this may include a scene where she beats the crap out of him. She was also Sonya Blade in 'Mortal Kombat' later that year, so she definitely had this toughness about her. She was a good character to contrast Billy's personality.
If you feel like turning off your brain completely for about an hour and a half, this is a good go-to for such a thing. You just sit back and laugh with this movie, and you don't for one second take anything seriously. Aspects of it might be a touch dated, but I can't help but have fun with it. Make no mistake, it is Adam Sandler in one of his silliest roles, so first-timers may not get quite as much a kick out of it. But one has to understand that this was when Adam Sandler was just leaving SNL, and he was such a hit with us kids that a whole bunch of us had his material on CD and would gather friends in a room, listen and laugh. A lot of his material is still openly available, and if you've ever been a fan, I recommend checking some of it out. This probably is my favorite Adam Sandler comedy, and has been since day one. It helped me find my random sense of humor, and I'm forever thankful.