The 20th Anniversary Of ‘The Wedding Singer’: A Reminder Of The Road Not Traveled For Adam Sandler

My earliest comedy memory is watching Adam Sandler on Weekend Update. Always portraying a buffoonish weirdo to juxtapose Kevin Nealon’s professional newsman persona, my introduction to humor stemmed from a bit in which Sander, portraying a travel correspondent, spent his entire Disney World vacation eschewing typical theme park folly for the familiar comforts of watching TV and playing in a McDonald’s ball pit. My 9-year-old mind was blown. Like countless other ’90s kids, I had become comedically smitten by the juvenile charms of Adam Sandler. “Canteen Boy,” “The Denise Show,” “Lunch Lady Land,” “Zagat’s,” “Gap Girls,” Sandler got me. His punk rock brand of humor provided a host of burgeoning comedy nerds something new, something different.

The comedian eventually graduated to the big screen with adolescent catnip like Billy Madison and Happy Gilmore; movies revered by teens but panned by critics for their lack of substance. The films were a commercial success, but the general consensus among the mainstream media was that Sandler was a low-brow actor who could only appeal to the Beavis and Butt-Head generation. That perception evaporated on February 13, 1998 with the premiere of The Wedding Singer.

The Wedding Singer is Adam Sandler’s best comedy. In the schmaltzy world of rom-coms, the film is a symphony of superlatives as Sandler and Drew Barrymore exude a buoyant chemistry while telling a simple, sentimental love story. Critics who wrote Sandler off as a gibberish-spewing, Bob Barker-punching jester had to reevaluate the Sand Man’s theatrical prowess. The actor excelled in the role of lovelorn everyman Robbie Hart. As soon as Sandler softly cooed that he’d “even let Drew Barrymore hold the remote control,” it was clear he possessed the innate talent and charisma to be Hollywood’s preeminent rom-com leading man.

But it was a title he had zero interest in claiming.

Sander followed The Wedding Singer with the commercially successful film The Waterboy and immensely underrated comedy (don’t @ me) Big Daddy. In the span of 16 months, Sandler starred in three bonafide hits. But his post-2000 career has been a peculiar hodgepodge of ups, downs, and the movie Jack and Jill, a film so universally loathed it prompted Tom Long of The Detroit News to write “the apocalypse starts here” in his review. But if it really is the end of the world as we know it, Adam Sandler feels fine, and for some fans, that’s the problem.

The Wedding Singer proved that Adam Sandler is capable of so much more than broad comedy. Respected leading man? Consistent rom-com star? Academy Award-winner? Absolutely. Oscar-winner Adam Sandler is not as ludicrous as it sounds. His revelatory performance in Punch Drunk Love earned him a Golden Globe nomination and there was more than a whisper of Oscar buzz for his portrayal of Danny Meyerowitz in The Meyerowitz Stories.

But who cares, right? Unfulfilled potential is nothing new, especially in Hollywood, so why is there so much vitriol towards the majority of Sandler’s post-2010 movie career? I believe it has to do with the fact that to a generation of ’90s kids, Adam Sandler wasn’t just a guy, he was thee guy. He was our guy. He embodied the anti-establishment. Fans will forgive bad movies, but the contrast in quality is just too stark to dismiss. It’s not that the last ten years of Sandler’s career is just forgettable, it’s that the majority is insultingly repugnant.

“Two roads diverged in a wood
And I— I took the one less traveled by
And that has made all the difference”

— Robert Frost

“Cindy and Scott are newlyweds… Whoopee-dee-doo!”

— Adam Sandler, The Wedding Singer 

Sandler’s taste in movies didn’t evolve on the same trajectory as his initial fanbase. Moviegoers who expected the comedic hero of their youth to mature into the cinematic standout of their twenties and thirties were disappointed. If you were obsessed with Happy Gilmore at 14, chances are you’re not loling at the madcap shenanigans of The Do-Over at 33. Considering thinly-veiled cash grabs like Grown Ups 2 have become the norm as opposed to the exception, fans feel betrayed, like the mere existence of the cinematic sewage known as The Ridiculous 6 somehow invalidates their nostalgia. On an intellectual level, that’s ridiculous, but on an emotional level, it’s understandable. Unrealistic expectations alter perception and breed resentment.

The fact that people care so damn much is a testament to Sandler’s talent and enduring legacy. I may not be the target audience for, well, almost everything after Funny People (The Meyerowitz Stories being the exception), but I don’t personally begrudge the Sand Man for these movies. Sure, I think they’re lazy, meteorically abysmal films, but if a studio offered me a yacht full of cash to make a slew of shitty movies with my best friends, I’d be on the the set of the buds on a boat comedy Grown Ups 3: Y.M.C… Mayday? tomorrow.

We all would.

Few actors possess the dynamic combination of humor and pathos of a motivated Adam Sandler. He’s shown that he can be a deft, nuanced actor, when he wants to be, and that’s why it’s so maddeningly frustrating to be an Adam Sandler fan.

The Meyerowitz Stories provides long-time Sandler supporters a glimmer of hope that a career renaissance, at least in terms of quality, may be on the horizon. But even if it’s more of the same uninspired drivel aimed at the lowest common denominator, we’ll always have the ’90s. The fact that Grown Ups 2 exists doesn’t cheapen my enjoyment of The Wedding Singer. Jack and Jill doesn’t nullify the happiness Billy Madison once brought me. I’ll keep watching. Why? Because Adam Sandler has the microphone and I don’t, so I will listen to every damn word he has to say.

Where to stream The Wedding Singer