In the mid 90s, former “Saturday Night Live” cast member Adam Sandler made two films that would not only make him a household name, but would help him ascend to stardom and a box office name for at least a decade. Those films, “Billy Madison” and “Happy Gilmore” also touched a nerve with me (just into my young teen years at the time) with their irreverent and absurdist humor. I didn’t think much of him when he was on “SNL” because he mainly played characters with goofy speech impediments, and felt like each was recycled from the one before.

This should have been a strong red flag for what was to come with his career. And in hindsight, it really was.

The Good…

But I, like many, found that Sandler can be funny with those two films. His first two comedy albums spoke to the crass and juvenile humor I loved at the time (they really didn’t age well at all for me after I turned 15) and for a short time there in that grungy, flannel-clad and self-obsessed era of Gen. X angst in the 90s, Sandler made it OK to laugh at weird, weird stuff — it didn’t have to make sense, as long as it was funny.

The thing I loved about “Billy Madison” (and to an extent, still do) was that despite the fact it has a ridiculous plot (grown man repeats every grade in school so he can take over his family’s business), that plot really takes a backseat to the absurd jokes and one-liners that make the film memorable. Hell, it seems they wrote the story’s plot around scenes like this one just so it could be in the film:

The same argument can be made for its follow-up, and perhaps Sandler’s best film, “Happy Gilmore.” While this was certainly more plot-driven than what came before, it still balanced weird, absurd humor with its story. I still quote lines from this film randomly in conversations and on Facebook and Twitter.

And maybe what really made these two films work was the fact that Sandler himself really isn’t the funniest part. For the most part, he’s the straight man to the weirdness around him with the other characters. And it worked very well for the films. Those side characters work well in the small doses we get of them, and brought some chaos to these worlds.

He followed these up with “The Wedding Singer,” which was also pretty good, but fell short in what I loved about his films: the weirdness. This would also be the last time I could call an Adam Sandler movie “pretty good.”

The Bad…

I started really questioning what Sandler thought his audiences thought was funny with “The Water Boy.” This, looking back, was the beginning of a downward spiral of Sandler films that  felt like he was there for the paycheck and giving the people a cheap knock-off of “Madison” and “Gilmore.” Sure, it was absurd. Sure, it had funny moments. But on a whole, it fell flat for me. “Big Daddy” also did nothing for me.

In 1999, he started his own film company, Happy Madison Productions. Despite being named after his two best works, it has ultimately proved to be a garbage machine that craps out terrible films for what feels like every other month. It still does, and now it will toss heaping piles of hot garbage upon Netflix.

The last Sandler film I got a chuckle out of came out soon after this company was started. “Little Nicky” showed a glimmer of hope that Sandler still had the chops to make a ridiculously fun movie. I remember not being impressed with it, but not necessarily hating it. That hatred of Sandler films would come not too much later.

The Ugly

It was when I walked out of the movie theater after seeing “Anger Management” that I vowed never to pay to see another Sandler movie again. I had seen “Mr. Deeds” not too long before, and was quite possibly the first time I got pissed off for paying to see a movie. “Anger Management” took that anger, and multiplied it ten-fold. He wasn’t even hiding the fact he was simply phoning it in, and his films were becoming the worst garbage I am embarrassed to even admit I have seen.

I had the unfortunate experience to catch “Eight Crazy Nights,” his animated travesty of a film that somehow made me despise Sandler more. That was then I decided that I simply could not stand his films to the point that even watching them for free was too much of a chore. How could someone who obviously does not care what he slaps his name on still be making such box office hits? It was like he was openly daring people to hate him, like he wanted us to despise anything he did. He was just doing those terrible, one-note goofy voiced “SNL” characters again, but making feature length film about them.

The Exception

In the middle of his wretched output, Sandler did put out a film that was not only good, but that I thought was great. That would be “Punch Drunk Love,” a film by Paul Thomas Anderson that I had put off from seeing on the sole fact Sandler was in it. But outside the clutches of Happy Madison and his own control, and in the guidance of a very, very good director, Sandler gave a very impressive performance that almost made me forgive him. Almost. I realized that Sandler can do good work, but he openly chooses not to. He hasn’t been in a decent film after this, and rarely in a film outside his own production company.

Conclusion

Maybe Adam Sandler never really changed, and I just grew out of his tired shtick. Maybe. Maybe I look back on “Billy Madison” and “Happy Gilmore” through those rose-tinted glasses of nostalgia of my youth. Maybe. The problem with that theory is I still find those early films funny — not as funny as when I was just a little snot of a teenager, but still amusing. I recognize that my taste in comedy have evolved since my early teens, and that’s a good thing. Yet, it feels like Sandler’s taste in the comedy films he makes has devolved over the years. Probably out of laziness more than anything, because we have proof he can make a funny movie.

What the hell happened to Adam Sandler? He doesn’t make it a secret he really doesn’t try anymore, and sees making a film as a goof-off vacation for himself and his buddies. His movies are generally considered terrible, and yet he continues to pump them out even when the films seems to disrespect an entire culture for no real good reason. He appears on TV interviews in sweat pants, looking like he’s given up on life.

My best guess is that once he was financially comfortable, he no longer cared what he did as long as it kept him in that comfort zone. Whatever the case may be, there was a time when he actually made funny movies, and he can at least look back on his very checkered career and know that he once did something of worth.