In 1994, Adam Sandler played his first real movie role as Pip, the brainless drummer in the hilarious rock-comedy Airheads. Who could have known that nearly 20 years later, the often polarizing comedian would still be headed to Hollywood premieres for his new movie coming out this Friday: That’s My Boy.

Success

For Sandler, the mid to late 1990’s were a dream for him and his legion of fans. What with Billy Madison becoming such a major hit, and following up with the even more hilarious hockey player turned golf pro in Happy Gilmore. He seemed even more unstoppable during 1998, seeing both The Water Boy and The Wedding Singer become monster hits, but who’d have ever imagined that this may have been his swan song?

After Big Daddy’s success in ’99, he looked to be on a mission to assemble a bad movie montage with a string of massive failures.  From Mr. Deeds to the abysmal Click, he peppered our weekends and summers throughout the the next decade with many films, few worth their ticket price, but alas he continued to find(or create) roles for himself and his band of actor buddies. I feel like it finally sunk in that the days of Happy Gilmore and Billy Madison were all but lost when he played an Israeli counter-terrorist turned hairstylist in: You Don’t Mess with the Zohan. Despite its financial success, it was panned by fans and critics alike.

Depressed

Perhaps this is why he decided to play a depressed and cancer stricken comedian in the 2009 dark buddy comedy, Funny People. Banking on new hot commodity Seth Rogen and the recent success of his big hits Knocked Up, Superbad, and Pineapple Express. Many fans thought this would be Sandler’s true come back to quality comedy, but it just didn’t seem meant to be. The film ended up being more depressing than funny and bombed in theaters.  Unable to break even with its production budget of $75 million.

Once he made Just Go with It and lured Jennifer Anniston and Brooklyn Decker into bikinis for the only two good reasons to see the movie, we realized he had all but forgotten his comedic glory days. After growing up with his greatest hits from the ’90s, it was honestly depressing to see him flounder in such comedic failure.

Optimist

Sandler, ever the optimist, continued to find or create movies to star in. Sadly this included his most recent comedy Jack and Jill, which one could argue was the lowest point of his career. Jack and Jill, despite doubling its estimated budget of $75 million in world wide box office receipts, received an emasculating 3% rating on Rottentomatoes, making it his lowest rated film to date.

Perhaps he thought playing two bad characters could increase his chances of being funny, but somehow he ended up making even Al Pacino appear terrible on the big screen. Not exactly an easy feat.

The man we couldn’t live without growing up has turned into comedic poison and yet he keeps receiving comedic roles and you know what? It’s all our fault. We’re his audience and while we were busy growing up, someone forgot to mail Sandler the memo.

Future

His new movie That’s My Boy comes out this Friday and the previews make the film appear fairly promising. Especially with hilarious sketch comedy actor Andy Samberg along side him playing his son, who looks like a spitting image of young Sandler.

The verdict is not exactly out yet, but we might be looking at adding to the ever rising pile of Sandler comedy bombs in the near future, which is a bit sad when one sits back to reminisce. Those of us who grew up with his films adored him, and repeated his hilarious one-liners on a daily basis with our friends. Now we’re basking in the epicness of his failures.

But Adam Sandler fans, you needn’t worry about our childhood comedic gem. If nuclear fallout were to ever occur, I assure you he’ll be the last comic standing, and there’s not a doubt in my mind that he’ll still be churning out comedy classics.