Billy Madison (1995)

This week for Disc Dive we’re going back to school. So make sure your lunch is packed up, your boots tied tight, and here’s hoping we don’t get in a fight with Billy Madison.

Title: Billy Madison

Director: Tamra Davis

Released: February 10, 1995 (Theatrical – Canada and the United States)

Runtime: 1 hour 30 minutes

Disc Format: DVD

Billy Madison (Adam Sandler) is the stereotypical spoiled man-child. His father, Brian (Darren McGavin), is the head of Madison Hotels. This provides Billy with the ability to lounge around the pool, go out causing mischief, whatever tickles his fancy on any given day. For Billy Madison, life is good.

Though change is in the air.

When talking about a succession plan, Brian isn’t convinced that Billy would be responsible enough to run Madison Hotels. Because of this, Brian has decided that control of the company will be passed on to current Vice President, Eric Gordon (Bradley Whitford).

Billy tries to plead his case when his father drops another bombshell on him; the only reason Billy made it through the 12th grade is because Brian bribed all of his teachers. Shaken, Billy proposes a plan. He’ll repeat grades 1 through 12, spending 2 weeks in each grade.

If he’s successful, Madison Hotels becomes his. If he fails, his family legacy winds up in Eric’s grimy little hands.

Billy Madison is a film I’ve seen dozens of times. During this viewing I realized that I can still recite around 85-90% of the dialogue word-for-word.

The supporting cast is what makes this film. For starters you have Sandler’s SNL friends Norm Macdonald and Chris Farley, each making their limited screen time count in exactly the way you’d hope. The children in elementary school that Billy interacts with have the simple innocence of being kids that helps elevate the comedy in their scenes. Then you also have Billy’s teacher Miss Lippy (Dina Platias) and Juanita (Theresa Merritt) the maid, who each have their own memorable moments as well. But from the supporting cast, the standout for me is Bradley Whitford as Eric. In fact, this is up there with Cabin in the Woods for my favorite roles of his. His back-and-forth with Sandler holds up as one of the comedic highlights of the film.

Speaking of the Sandman, this is probably one of my favorite comedic roles from Adam Sandler. And that’s saying something, because for every Billy Madison or Happy Gilmore there’s a Jack and Jill or The Do-Over. Like most everyone else, I’ve enjoyed the more serious route his career has taken of late, but this is a reminder of how good he can be when the comedy clicks.

When it comes to pacing and structure, this holds up quite well. The two weeks per grade stipulation makes sure things keep moving and we don’t dwell in one grade for too long. With a runtime of 90-minutes, even when a gag might not stick the landing, we’re already on to the next one.

Whether it’s wondering how a penguin is surviving in a warm climate, demanding a snack pack, telling the kids that they aren’t cool unless they pee their pants, or trying to fit in at high school as an adult, Billy Madison never fails to make me laugh.