Blended’ - the latest movie starring Adam Sandler and Drew Barrymore - isn’t a horrifically bad movie. It’s actually even a little better than what you’d expect from Adam Sandler these days – but I did find it terribly depressing to watch.

It’s easy to go back to Sandler’s somewhat “artistic” phase – with movies like ‘Punch Drunk Love,’ ‘Spanglish,’ ‘Reign Over Me,’ and maybe even ‘Funny People’ – and let out a exasperating sigh of what happened? (I’ve thought about this more often than I should.) But, while watching ‘Blended’ -- what is now Sandler’s third collaboration with Drew Barrymore – I’m drawn back to their first outing together: 1998’s ‘The Wedding Singer,’ which inherently makes me sad. (Not to even mention that Alexis Arquette briefly reprises the role of George in ‘Blended.’)

Not counting a few smaller roles in movies like ‘Airheads’ and ‘Mixed Nuts,’ by the time ‘The Wedding Singer’ (which, like ‘Blended’ was also directed by Frank Coraci) was released, Adam Sandler had starred in three movies: ‘Billy Madison,’ ‘Happy Gilmore’ and co-starred with Damon Wayans in ‘Bulletproof.’ By this point, Sandler’s characters were best known for being crass, loud, and vulgar man-children. Both ‘Billy Madison’ and ‘Happy Gilmore’ made money, but neither were box office behemoths anywhere other than at your state university’s local Sig Ep house.

‘The Wedding Singer’ was Adam Sandler’s first true hit movie. Sure, it helped that the movie was already playing toward the already-burgeoning nostalgia for the 1980s. (It’s weird to think ‘The Wedding Singer’ takes place only 13 years after the year it depicts; it would be like a nostalgia comedy being made today being about 2001. Instead of the film opening with Sandler signing "You Spin Me Round (Like a Record)" by Dead or Alive, it would open with Sandler singing "Thank You" by Dido.)

More importantly, from a Sander career growth perspective, ‘The Wedding Singer’ was a true step forward for Sandler as a leading man. All of a sudden, people saw his appeal: He could actually be charming and sweet and finally, in this film, let his guard down. In other words: It was the first time that Adam Sandler acted like a real life human being.

In ‘The Wedding Singer’, there’s a real optimism in Sandler’s performance. Sure, he allows himself a few moments in which he rants and screams, but compared to his past films, that aspect of his performance had been toned down considerably. It’s almost endearing, watching a young Sandler as a depressed wedding singer named Robbie Hart, who slowly falls in love with a young Barrymore, a woman named Julia who is engaged to a man named Glen Gulia. There’s so much hope! It’s a story about the promise of the future -- both for Robbie and Julia, but also for Sandler. ‘The Wedding Singer’ grossed $123 million worldwide and officially made Adam Sandler a movie star.

In ‘Blended,’ Sandler plays a widower with three daughters, while Barrymore plays a divorcee with two sons and, through a series of events too convoluted to write out, they all wind up in South Africa staying in the same hotel room. These are not the same characters from ‘The Wedding Singer’ or even ’50 First Dates,’ which makes sense, a lot changes over the course of 16 years. But that’s exactly the problem here for Sandler – because really nothing has changed for him as a performer. It’s the same shtick over and over and over again. ‘Blended’ is nowhere as near as entertaining as ‘The Wedding Singer,’ but it tries to hit the same beats that all of these movies of his hit. Do you like it when a random character says something mildly offensive while Sandler makes a funny face, right before transitioning to an entirely different scene? There are plenty of those for you in ‘Blended.’ Do you like Allen Covert cameos? That’s here, too.

Again, ‘Blended’ isn’t terrible, but it’s lazy and every single one of these types of Sandler movies makes me more and more sad about what could have been.

I do wonder what would happen if someone showed ‘Blended’ to Adam Sandler back in 1998. I tend to think that he’d be mildly pleased, like anyone, that he still has a career, but be disappointed that he’s making movies that are less ambitious than the one that he just made. Then again, maybe not: Sandler is a hard guy to read and was still four years away from his first true challenge in Paul Thomas Anderson’s ‘Punch Drunk Love.’

Back in March of 2007, Adam Sandler was scheduled to be the first guest on ‘Late Show with David Letterman.’ Letterman had come down with the stomach flu, but instead of canceling the show, Sandler wound up hosting the show.

It’s fitting that Sandler was there to promote ‘Reign Over Me,’ one of the last examples of him allowing himself to be challenged as an actor. Because I do believe that this incident on the ‘Late Show’ was also one the last moments that Sandler has challenged himself professionally. Sandler accepted that challenge and wound up being a pretty good talk show host. Gone was his trademark slob look (I like a good Mizzou t-shirt as much as anyone, but, c’mon, you’re on national television), replaced by a nice suit. The Sandler we watched that night acted like an actual human being and we liked that guy.

Sandler can be a deft comedian when he wants to be – and, more importantly, Sandler let his guard down for an evening. (Trust is a big issue for Sandler, who famously won’t do print interviews.) And I think that’s why so many people (me included) still give him the benefit of the doubt, because we all know that guy is still in there -- the guy who was smart enough to let his guard down in ‘The Wedding Singer,’ which finally opened all of the doors Sandler wanted.

Eventually, Sandler himself closed those doors – but yet I still hope that someone comes along, someday, who can really challenge Sandler again. And, more importantly, that Sandler will accept that challenge. Maybe that’s going to happen with Jason Reitman’s ‘Men, Women & Children’ or Thomas McCarthy’s ‘The Cobbler.’ Back in 1998, Sandler couldn’t predict what his future would look like 16 years later, but unless something changes, I think we all have a pretty good idea what Sandler’s professional future looks like now.