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Do you remember when Adam Sandler used to make dumb movies that were actually funny?

Think hard. Movies like “Billy Madison” and “The Waterboy” featured the comedian in ridiculous, lowbrow situations that somehow worked. Back in the 90s, Sandler’s boyish charm and absurd delivery allowed you to believe that it might be possible a rich kid would repeat kindergarten through 12th to win the respect of his father. Or that a downtrodden hockey player could become a professional golfer because he can smack the crap out of the ball and had Apollo Creed as his coach.

But Mr. Sandler is now in his mid-40s and the boyish charm has withered and died. The recent release of his latest idea of entertainment, “Jack and Jill,” has proven that Sandler has gone from making dumb movies that are actually funny to making movies that get caught up on the dumb part and never make it around to the funny.

“Jack and Jill” features Sandler in dual roles and allows the former master to play his own sister. The concept belongs with the fake trailers that opened Ben Stiller’s hilarious “Tropic Thunder” a few years back. Sandler in drag is something that would fit right along side Jack Black in a fat suit for “The Fatties Fart 2”. Last year we had “Grown Ups,” a film that brought Sandler together with a group of his big name, comical buddies (Chris Rock, Kevin James, David Spade et al.) and let the group duke it out and see who could be the least amusing (Rob Schneider won).

The situation is reminiscent of another mega-star funny man: Eddie Murphy. Mr. Murphy made a few classics in the 80s (“Beverly Hills Cop,” “Coming to America”) but then got too big for his own good. Once you start demanding $20 million dollars to show up to the set, the list of projects narrows and next thing you know you’re making “Daddy Day Care” on the heels of “Doctor Dolittle 2”.

That excuse only goes so far with the Sandler situation, however, because he is actually writing and producing these things. It’s his own fault that we now have the image of Adam Sandler with boobs seared into collective consciousness.

These films are getting so absurdly bad that it makes you wonder if he is doing it on purpose. That it’s all a master plan. How weird is it that he plays a tired, sold-out actor in “Funny People” who has had enough of playing wacky characters in terrible films like “Mereman” and then goes on to give us “Jack and Jill”. Could Sandler be testing us by making the most ridiculous movies he can imagine and see if the masses flock? Or is he just out of ideas?

Adam Sandler would be better off leaving the joke writing to other people. Maybe it’s time to focus on the more serious, obscure roles that he has dabbled with in the past. Another “Punch-Drunk Love” might cleanse the palette. Sadly though, as long his movies make money (“Jack and Jill” opened to $26 Million!) we should expect more of the same. “Click 2” anyone?

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