Why I Fell in Love With Adam Sandler — And Why We Had to Break Up

I was a junior in high school when I first fell for Adam Sandler. It was February 1996, and the former Saturday Night Live star’s breakout comedy, Billy Madison, had finally arrived on VHS, and its superior follow-up, Happy Gilmore, had just been released in theaters. To me, the one-two combo was proof that Sandler wasn’t merely a comedy genius; he was, in the obnoxiously grandiose words of Billy Madison himself, “THE SMARTEST PERSON ALIVE!” Like millions of other teenagers, I loved him for it.

It wasn’t just Sandler’s oddball, aggro comedic sensibility — what with its penguin hallucinations and game-show-host beat-downs — that earned my devotion. Sandler was also an antihero perfectly suited to an adolescent boy; he stood up to the very douchiest of douchebags, always got the girl, and stubbornly refused to grow up. Sandler’s antiestablishment attitude, whether directed toward snooty country club members or jerky teachers, proved that one could get older without necessarily ever maturing. He packed dozens of memorable one-liners into every film that my friends and I repeated constantly, in-jokes that only true Sandler lovers would get, like “Stop looking at me, swan!”

As I moved on to college, Sandler remained close to my heart as he grew (slightly) into a sweet-meets-sophomoric phase that included The Wedding Singer (1998), The Waterboy (1998), and Big Daddy (1999). I was growing, too — though, in true Sandler style, I still hadn’t grown up. When a college girlfriend insisted we rent The Wedding Planner, saying that it might help our relationship go “to the next level,” I showed her The Wedding Singer instead. It worked. Billy Madison would have been proud.

I remained Team Sandler into my young professional days, even as I could feel my fandom dwindle and teeter toward ambivalence. The first bump was Little Nicky (2000), which felt like spending 90 minutes in hell. Sandler’s unexpected dramatic turn in Paul Thomas Anderson’s Punch-Drunk Love (2002) was a pleasant surprise, though; it reignited our flame, especially as I felt my tastes evolving (maturing?).

Punch-Drunk was enough to get me through the rocky mid-’00s, in which he churned out increasingly formulaic comedies like Anger Management (2003) and Click (2006). I stuck with him, even though there were some more attractive fish in the sea: Judd Apatow had arrived on the scene, and an R-rated comedy renaissance was afoot with 2005 gems like The 40-Year-Old Virgin and Wedding Crashers. These movies were dumb/smart: They were the adventures of stunted guys, but there was a cleverness behind their adolescent jokes — the people making these films were obviously adults.

In retrospect, it was clear Sandler and I were on the rocks, though our breakup dragged on for years. It started in the summer of 2007, right around I Now Pronounce You Chuck & Larry. It wasn’t just horribly unfunny, it was icky and outdated — full of gay-panic undertones and over-the-top stereotypes. Then came You Don’t Mess With the Zohan (2008), which found Sandler feebly attempting an Israeli accent and bombing with “smell my feet” jokes as a Mossad-agent-turned-hairstylist. But it was 2011’s Jack and Jill, in which Sandler plays male and female twins, that finally made me realize we were through. For the first time in my life, I actively avoided a Sandler movie. I was too embarrassed to be in the same room with him.

It’s been nearly 20 years since the first throes of my Sandler crush, and as we all do with our exes, I occasionally find myself wondering what’s going on in his head these days. Does he look back on the foolish choices he’s made in recent years — all these shameless cash-grabs aimed at the broadest, lowest common denominator — with regret? Does he look at actors like Seth Rogen and Jason Segel, whose man-child characters are allowed to actually become men, and secretly envy them? Or does he truly just not care, and making movies is just an excuse to hang out with his friends?

And, of course, I find myself thinking about who’s to blame for our failed affair; I don’t think it’s me. It’s strange to think I’m the mature one in this scenario. After all, I still laugh at lowbrow gags in spawn-of-Sandler films like Neighbors and This Is the End. But the truth is, I’ve moved on and grown up. Sandler, meanwhile, is still stuck in grade school.

Sandler has a new movie out this week called Blended, his third collaboration with Drew Barrymore. I won’t see it. But I will stand by my affection for Billy Madison and Happy Gilmore, because the earliest parts of a relationship are always the most fondly remembered. And whether it’s just nostalgia talking, they do still make me laugh.

So stop looking at me, swan.

Photo credit: Universal Pictures/Everett Collection