25 Years Later: ‘Billy Madison’ is Still Adam Sandler’s Funniest Movie

Billy Madison’s going back to school… Way back.

Few comedians or comedic actors of any stature are able to make such a quick transition from early stand-up to a lucrative TV job to international superstardom as quickly as Adam Sandler. While much of his success has to do with the accessibility of his material, the strength of his headlining role in Billy Madison cannot be overstated.

One of the ultimate screwball comedies, and easily one of the funniest movies of the 90s, Billy Madison is one of the easiest examples of a time capsule for the era, and a very funny one at that. Packed to the brim with wacky co-stars and hilarious cameos, the delightful absurdity of the film, from its premise to its increasingly silly plot evolution, makes it worth rewatching even today, where much of the comedic landscape has changed substantially.

The whole idea of the film oughta give you some idea of what a goofy runtime you’re in for when you sit down with Billy Madison. Ostensibly a perfect — if very dumb — metaphor for the questions of wealthy privilege in more modern times, Madison sees Sandler, as a grown man, allowed to repeat all twelve grades of his schooling in hopes of showing his father that he can take over the wealthy company that the senior Madison is stepping down from.

As the story continues, it becomes even dumber and more outlandish; but really, that’s part of its charm. Imagining the logistical hoops and legal restrictions that the Madison family is seemingly able to overcome with zero effort (and a pile of money) is just the tip of the iceberg for a movie like Billy Madison.

As Madison advances from one grade to another, he goes from making the kinds of crafts most parents throw in the garbage when their kids aren’t looking, to re-learning the basics of things like math, reading, and spelling. Like Homer Simpson and many other lovable dopes, Billy is often rude, almost always the dumbest person in the room, lacks any meaningful life skills, and yet somehow grows and perseveres through increasingly unlikely scenarios.

Along the way, he somehow attracts the romantic attentions of his 3rd-grade teacher (Bridgette Wilson), as well as the ire of his rival, Eric, who will stop at nothing to take over the company in Billy’s stead. Between these three characters, the main conflicts of Billy Madison occur, but the majority of the story is pretty inconsequential to the enjoyment of the movie.

Billy Madison Launched a Comedy Sub-Genre

Really, the central enjoyment viewers will draw from a movie like Billy Madison is found in the ridiculous plans, wacky adventures, and random occurrences that swirl around Billy like some kind of madcap hurricane. Hell, the movie starts with Billy chasing around a penguin only he can see in a golf cart. His next scene sees him battling shampoo and conditioner bottles in the bath, also supplying the dialog for these inanimate objects.

As a character quips later in the film, we, as the audience, may actually be dumber for having sat through this kind of deliberate stupidity of Billy Madison, but the script and Sandler’s man-child performance are so consistently funny that no one watching will care. If Chris Farley doing a striptease or an entire family launching off a cliff after hitting a banana peel doesn’t sound funny to you, then skip Billy Madison…but you’re definitely in the minority.

While Sandler would go on to essentially re-do this movie and role several times over the early years of his career, Billy Madison remains, even 25 years later, his best and most consistent straight comedy. Sure, the likes of Punch-Drunk Love and Uncut Gems make a movie like this look embarrassing by comparison, but as far as laughs-per-minute go, nothing in Sandler’s staggering 75-film career touches the consistency of Billy Madison. 

An absurd look at a time where comedies could be this stupid but still be enjoyable and endlessly rewatchable, Billy Madison didn’t just launch the movie career of its star — it also launched a whole comedy sub-genre, and helped bankroll Adam Sandler’s production company. Without Billy Madison, Adam Sandler wouldn’t be the star he is today, and (maybe despite that) the movie remains completely enjoyable a full 25 years after the fact.