Is Adam Sandler’s Best Movie Still ‘Billy Madison’?

Adam Sandler is now the subject of serious talk for his role in Uncut Gems. He won the Independent Spirit Award for his performance, and it’s not his first dramatic turn. Everyone may have their favorite Sandler movie but his very first cinematic vehicle, Billy Madison, may still be his best.

Adam Sandler | Universal Pictures/Getty Images

Billy Madison may be purest distillation of Sandler. There are other good ones: Happy Gilmore or the sweet Wedding Singer. Sandler is best when he’s playing absurd characters like the Zohan, but Funny People was a good combination of his comedic persona and self-reflective genre. Billy Madison opened February 10, 1995 and it’s really the one that started it all.

‘Billy Madison’: the ultimate Adam Sandler High concept

After his success on Saturday Night Live, Sandler started appearing in movies. His supporting roles didn’t propel Airheads or Mixed Nuts to box office glory, and Shakes the Clown barely even got released. But 1995, the last year Sandler was a cast member, he got his own movie.

Billy Madison (Sandler) is the son of a rich hotel magnate (Darren McGavin). Billy has been so coddled he’s not fit to take over the company. So he convinces his father to let him do first grade through high school over again, two weeks each, to show him he can earn the job. This would never happen in real life or hold up in business, but since they’re doing it the movie commits to the absurd premise.

‘Billy Madison’ is relentlessly stupid

Billy Madison allows Sandler to be unfiltered. There’s a pretty outrageous plot but just as many of the jokes are random. He sings the suntan lotion song and makes a smiley face. He also sings a silly “back to school” song like the kinds of songs he sang on Weekend Update. Later there is a full fledged musical number. He makes shampoo and conditioner fight. He feuds with an imaginary penguin. He dances to “I‘ll Tumble 4 Ya” on the stairs and he speaks gibberish.

Adam Sandler as Billy Madison
Adam Sandler as Billy Madison | Universal Pictures/Getty Images

Billy’s movie is as random as he is. Ms. Lippy (Dina Platias) pastes her eyes. Billy has a heartwarming phone call with Danny McGrath (Steve Buscemi) that ends with him putting on lipstick for no reason, and no judgment either. He returns as a hero. 

‘Billy Madison’ captures Adam Sandler’s Anger

SNL sketches may not have given Sandler much opportunity to get angry but anger would become a trademark of his persona, Especially Happy Gilmore and The Waterboy. Billy Madison may have laid the groundwork.

Happy Gilmore
Bob Barker and Adam Sandler in Happy Gilmore | Universal/Getty Images

Billy gets mad when his maid Juanita (Theresa Merritt) won’t give him a Snack Pack. He does the “Hahahahahahaha shut up.” The best is when he gets another third grader to call Ms. Vaughn (Bridgette Wilson) and when he steps in, he blames the kid and screams “You blew it!” There’s a great gif of “You Blew It” you can still use today.

‘Billy Madison’ lets Adam Sandler be the perennial manchild

Adam Sandler always acts like a stunted kid, but none of his other movies have as direct an excuse. In Billy Madison he’s literally back in school. He makes fart noises to appeal to first graders.

Third grade is where Billy most at home. That seems like the sweet spot where they’re old enough to get naughty jokes but still young enough to be silly. Billy does nice things for the kids too. He makes peeing your pants cool for Ernie (Jared Cook) in a really clever selfless display of “it the cool kid does it everyone follows.” It is also relevant that high school doesn’t think he’s cool. He turns it on them though.

Some of ‘Billy Madison’ is just wrong

Billy Madison may be silly, random and at times endearing but it never forgets that it’s just plain wrong to put a grown man in a class or schoolchildren. The dodgeball scene makes that point. He also makes fun of a stuttering kid reading but Vaughn calls him on it. He gets his comeuppance with cursive handwriting.

Some jokes are just wrong because we know better know. The She-male Fiesta nudie magazine could be just as funny using the appropriate trans terminology now. You wouldn’t use the r word either, even with a kid saying it.

Adam Sandler is a manchild but the kids are real kids

Billy Madison is a complete caricature but what makes him funny is dealing with a world that’s honest about how kids behave. During first grade story time Billy shares his opinion on a story the way kids state their opinions, only with an F-Bomb.

The O’Doyle bullies show how bullying runs in the family. In each grade they act the same but with slightly more force. The video game debate is 100% accurate to how third graders discuss pop culture:

3rd Grader: “Mortal Kombat on Sega Genesis is the best video game ever.”

Billy Madison: “I disagree. It’s a very good game but I think Donkey Kong is the best game ever.”

3rd Grader: “Donkey Kong sucks.”

Billy Madison: “You know something? You suck!”

That’s the extent of grade school conversation and it doesn’t get that much more sophisticated when you grow up and get on Twitter.

Shout out to Bridget Wilson

Bridget Wilson is the perfect foil to Sandler. She’s a good sport about being the “hot for teacher” object but she pushes back when Billy misbehaves. She also uses a teacher’s compassion to get him to see the error in his ways.

Bridgette Wilson-Sampras
Bridgette Wilson-Sampras | Online USA

Wilson was on a good streak of roles with Last Action Hero, this and Mortal Kombat. She kept working but her last role was in 2008. Her last big hit was probably as J-Lo’s nemesis in The Wedding Planner. She married Pete Sampras and has a family so hopefully she retired from acting on her own terms. It does seem like Hollywood neglected her talent. There never was a bona fide Bridget Wilson vehicle.

The ‘Billy Madison’ legacy

Other movies in which Sandler played outrageous characters include Happy Gilmore, The Waterboy, the underrated Little Nicky and You Don’t Mess With the Zohan. His romantic leading man persona worked to varying degrees in The Wedding Singer, Mr. Deeds, 50 First Dates and Bedtime Stories.

The rest have been variations on his everyman persona: Grown Ups, Just Go With It, Bulletproof, I Now Pronounce You Chuck and Larry. Click was sort of his everyman in a high concept fantasy. You can pick your Sandler, with even more options among his Netflix original movies, but he may never top Billy Madison.