EditorialMovies & TV

Guys, I Figured Out What Happened To Adam Sandler’s Career

Editor’s note: With the release of Grown Ups 2 sporting a snazzy 0% on Rotten Tomatoes, I thought it’s a good time to re-post this thing I wrote in October of last year, as it’s even more relevant now.

This weekend I realized the answer to a question I’ve been asking myself for some time, and it’s all because I decided to watch That’s My Boy on Netflix. Now, I know a lot of you are probably judging me for even considering watching this film. Even when you consider the infusion of Andy Samberg into a “modern” Adam Sandler film, the prospects of this one being any better, than say Go With It, are slim (and even that’s being generous.)

Now, Billy Madison and Happy Gilmore are some of my favorite comedies of all time. Big Daddy. The Wedding Singer, and The Waterboy are all pretty great as well, at the very least, they’re re-watchable.

When Little Nicky was released, it was a major disappointment. Mr. Deeds was okay, but I’d be fine never watching it again. Then every subsequent release from the former SNL star seemed to get more formulaic and, well, dumb. Yeah, Sandler has always been stupid, but in a charming way. All of a sudden, in the late 90s, it seemed that Sandler was no longer charmingly stupid, but slowly evolved into being just plain stupid.

For years, I thought that the now “20 million per picture” Sandler was just working for the next paycheck while he still had years in him. I thought that he was no longer inspired, and that it showed in the work.

As I watched That’s My Boy, I was so disheartened with my fallen hero, that I decided to look up his IMDB page and try to figure out where it all went wrong. Like a romantic relationship that goes awry when you’re not looking, there was just something missing, and That’s My Boy was the moment that I realized exactly how bad things had gotten.

I looked through Adam’s body of work and noticed a clear divide. There was that point after the release of Big Daddy when the movies went downhill. Then it hit me. “When did Sandler start working exclusively on films produced by Happy Madison, the production company he had started?”

I looked into it. The first film produced by HM was Little Nicky, the release that followed Big Daddy. Sandler released his first self-produced comedy and never looked back. Every (goofy) comedy that he’s stared in since has been produced by his own production company.


There have been moments of brilliance, that had been sticking points for me. I’d think, “If he lost the motivation to work, then how do you get Punch Drunk Love, Spanglish, or Funny People?”  His performances were great in those movies.

Well, as I looked through the list of films produced by Happy Madison, those works were absent. They were outliers, but not because they were passion projects. They were produced by other companies with other directors and producers. They’re not HM works, so they’re irrelevant to this point.

It turns out this decline had probably far less to do with inspiration or motivation than I had originally thought. My theory is that the issue has been one of too much creative freedom. Sometimes, the product that comes out of a brilliant performer is too “over the top” before being diluted by a producer or director. Then there are other instances when a performance needs to be pulled out when it’s not there initially.

When Sandler started Happy Madison, he gained creative freedom to make whatever he wanted. There were no producers or directors to answer to. He was the boss-man now, he gets the final word.

The problem, in my opinion, is that Adam had been working with studios, producers (production companies) and directors that were limiting him in the right ways, and who had also been pulling out better performances. With the new-found creative freedom that Happy Madison allowed, Sandler moved out of the “sweet spot” that he had thrived in.

Editor’s Note: It seems that the influence of producer Robert Simonds, is notably missing from the newer Sandler films. He worked on Billy Madison, Bulletproof, Airheads,The Waterboy, Dirty Work, The Wedding Singer, Little Nicky and Big Daddy, Which IMO, is Sandler’s best work. 

Sometimes, with the right combination of minds there’s this moment of creative harmony, and something amazing happens. For Sandler, that took place between 1994 (starting with Airheads) and 1999 (ending with Big Daddy)

Now, I know that there are a lot of artists out there, who will be annoyed by what I’m suggesting because creative integrity, blah, blah, blah. Personally, I think that creative integrity is often cited  when it’s really a cop-out. We’re all constantly learning and perfecting our respective crafts.

What does matter to me is having the right team assembled. With the right minds collaborating on a project, a superior product can result. The filmography of Adam Sandler is a pretty good argument for that.

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Chris Olivieri

Chris Olivieri

I'm a polymath with ADD, Entrepreneur, & ENTP whose aim is to emphasize awesomeness in pop-culture. I've described the contents of my mind as "Similar to Heffalumps and Woozles"