Billy Madison & Happy Gilmore – The Enduring Appeal of Adam Sandler’s Initial Masterpieces

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Carl Weathers And Adam Sandler In 'Happy Gilmore'
Carl Weathers talks to Adam Sandler in a scene from the film ‘Happy Gilmore’, 1996. (Photo by Universal/Getty Images)

There’s an inextricable link that makes it virtually impossible to discuss Billy Madison or Happy Gilmore without considering the other. The films began Adam Sandler’s transition from an SNL weirdo “deconstructing sketch comedy” to one of biggest box office draws of all time. Many arguments have been made through the years about when he stopped being funny, or at least stopped trying, but there is NO such debate around Billy Madison or Happy Gilmore. They are indisputable classics among a certain generation, two nonstop laughfests that stretch the definition of a feature film, yet captured the public’s long term collective interest. They are so beloved that Adam Sandler named a charity, which aims to provide work for his less talented friends, after the films (Happy Madison). You simply can’t deny the comedic genius and inspiration on display by a younger, skinnier, shout-ier Sandler when he first made the leap to the silver screen.

Released almost exactly one year apart, Sandler’s first two starring vehicles (you don’t count, Going Overboard) are undeniably similar. Both center on an indignant, fervid man-child played by Sandler, who learns to grow up and gain relative control of his emotions with the illogical love of a good woman (each with the initials, V.V.). The storylines weren’t galvanizing anyone, but they weren’t the draw; this was about pure, unfiltered Sandler, and boy does he deliver. There’s a distinct lack of complacency here, an obvious desire to demonstrate his unrivaled gifts to the world. The knowing distance he specialized in, a smirking awareness that he knew just how ridiculous this all was (as he then does the most inane thing), is on full display. Perhaps it was the lack of his superduperstar safety net and, coming off his firing from SNL, an uncertain future in Hollywood, but Sandler is fully committed to both asinine roles.

Neither film was a massive financial success, and are the only ‘Adam Sandler comedies’ to earn less than $50 million at the box office. Happy Gilmore almost doubled the income of its predecessor, with a slightly more coherent story and less joke-and-bit-delivery structure. Both display some early outlines of the template Sandler would use for his astronomically successful faze: schlubby dude is redeemed by way-too-good-for-him woman and/or family, and ends up happier and wiser in the end. This is more pronounced in Happy Gilmore, which features a schmaltzier ending than Billy Madison, and the comparative plotting of a taut thriller.

Seriously, Billy Madison is a fucking bizarre movie. Norm MacDonald’s character shouting at the end, “Yahoo for Billy! Billy’s number one, yahoo!” is essentially a mission statement. It seems to exist exclusively as an excuse for Adam Sandler to deliver some of the most outrageous, memorable, and, yes, immature gags of his career. There’s an avant-garde quality to the whole thing, an almost ‘punk rock’ aspect to the film (as described by Marshall in Undeclared). The story is sheer lunacy, with Billy’s millionaire father arranging him to retake grades 1-12 (in two weeks each) to “earn” the right to take over the family’s fortune 500 company. It features running subplots about an imaginary penguin; of a clown smacking his head on concrete in seeming death, as kids look on laughing; and Steve Buscemi as a lipstick-wearing former high school classmate of Billy’s who keeps a kill list. This isn’t the place to go if you’re looking for well drawn characters and coherent storytelling. It wraps up with an “academic decathlon” (“what does that mean?…Carl, what does that mean?”) and mock game show at a high school auditorium (“Knibb High football rules!”), because that’s a real thing that happens. Seriously, the movie’s second-to-last image is the aforementioned imaginary penguin jerking off Chris Farley, for God’s sake.

Even with a snivelling, memorably weasley antagonist in Eric (Bradley Whitford at his slimy best), who was set to inherit the company if Billy failed, there’s never a sense Billy won’t succeed. The only thing of importance was, again, laughs, and lots of ‘em. And lordy, are there a ton of quotable lines from the movie: “Old Man Clemens hates shit!” to “maybe if you’d told me there were delicious triscuit crackers in the car,” to “Chlorophyll…more like Borophyll!” and an old lady declaring “if peeing your pants is cool, consider me Miles Davis” (immediately after said old lady blames a lunch theft on “that damn Sasquatch”). l have absolutely no idea how the musical number that beckons the final act came to be or what its purpose was, but I know every word and can sing it to you anytime (if I need a piece of gum). That’s the kind of movie Billy Madison is. It wasn’t dictated by logic; it was dictated by laughter, come hell or high water (speaking of water, “stop looking at me swan!”).

Happy Gilmore is a spiritual successor, and seemed designed to capitalize on everything we loved about Billy Madison while providing a sturdier framework for the story. A heavy-handed opening narration informs us Happy is an orphan raised by his grandmother who’s obsessed with hockey. He has a killer slapshot and a legendary temper (“I hold a record, I’m the only guy to ever take his skate off and try to stab a guy”), but can’t skate. It’s never remotely addressed how he’s supposedly trying out for a professional team when he can’t stay upright on ice, but it’s irrelevant. His grandmother owes over 100K in back taxes, has to vacate her home until she can pay, and through highly convoluted means, he discovers his ability to drive the ball over 400 yards (“you hit that guy!”). He heads to a driving range to demonstrate his skills as the “amazing golf ball whacker guy,” and is recruited by club pro Chubbs Peterson, with his wooden hand from a “damn alligator” biting it off (“oh my God!”). Within seemingly days, he’s winning a qualifying tournament and has made the PGA tour.

While I noted this movie has a more coherent and recognizable plot, I didn’t say it was any less absurd that Billy Madison. The idea that a failed hockey player could drive a golf ball crazy far and become a pro, in spite of a complete lack of experience, accuracy, or short game skills (“just taaaaaap it in”), is preposterous. But that he needs a lot of money fast to save his grandmother’s house, before a tax auction deadline, does drive the plot forward more conceivably than a grown man re-entering grade school (barely). It makes sort of sense that he would pursue this completely random career path, given the financial opportunities available, when he discovers the hidden talent. So Happy joins the tour, flirts with the PR rep (Julie Bowen!) by alerting her that his “girlfriend fell off a cliff and died on impact,” and spars with a sleazy rival, Shooter McGavin. You know where it goes from here: Happy fails, his grandmother is stuck in the nursing home (with sadistic Ben Stiller), Shooter wins and walks away with the girl. Just kidding! Of course it all works out in the end, even for dead Chubbs, who gets his hand back in heaven (and serenades Happy with “We’ve Only Just Begun” in the happy place).

Between Shooter and Eric, the idea of a formidable, concrete opponent for Sandler’s protagonist keeps him immersed. If he had a charismatic foe, he couldn’t phone in his performance and risk losing the audience. Eric is fantastic, but Christopher McDonald is LEGENDARY as Shooter, in what may be the greatest villainous performance of all time (give or take). He’s a condescending, smug douche who feels foisted by Happy’s mere presence on the tour. Whether he’s chastising the press for not talking up his winning performance enough, or dedicating a round to Chubbs’ death because he “called it first” before Happy (“congratulations, murderer”), he’s the perfect thorn in the protagonist’s side.

That presence of a strong heel seemed to bolster Sandler’s performance in both films, keeping him engaged. And when he was engaged, he was turbulent, and a screeching mad Adam Sandler is by far the best kind. Those irrational outbursts of rage, punctuating his goofy voices and dopey antics, were the key to his prowess. There was nothing like it, and as he slowly moved away from these types of roles, focusing on becoming a bajillionaire, those captivating and unpredictable parts faded further into memory.

Adam Sandler never truly stopped trying, as much as deciding to aim beyond a narrow portion of the film watching public. There’s genuine logic to the coldly calculated career choices he made as his star shown bigger and brighter. We wish he stayed true to his art, to what made him such a unique once-in-a-generation talent, yet how many of us can honestly say we’d have taken a different path in his stead? So we can’t really blame him as we shake our collective fists and decry his decision to stop taking chances. We’ll tear him apart for the cynical resolve to seek broadly low brow comedies and lazily pandering family features. And we’ll claim ownership of these films, like so many fanboys out there, trying to dictate an individual’s life and career to them because it’s IMPORTANT to us. But Adam Sandler is who he is as a comedic actor now, for better or worse, so maybe we ought to just save our energy and remember the good times. Because even two decades later, Billy Madison and Happy Gilmore are still some pretty damn fun times.

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