How this could have been a good movie
This could have been a good movie. I think the thing that really kills it is the end.
At the end, Zack (Dane Cook) does win employee of the month and get the girl, which is... well, it's nice... it is a notable achievement for the environment he's in.
But the whole thing is so... lowball. Now, that is partially the point. After all, the movie is called "Employee of the Month". It's about the irony of achievement on a diminished scale. One can become "Employee of the Month", or even "King of the Cashiers", but even if one achieves that, one is still "just" an employee or "just" a cashier. (Even if you've made an art out of being a cashier.)
Ok, all this is a good recipe for comedy, but it's bad for drama.
In short, the problem with this movie is, at the end, Zack is still a cashier.
What's wrong with being a cashier? Nothing... if that is your life's ambition, or if that's a stepping stone to your life's ambition. And what's wrong with being a good cashier? Nothing! If that's where you at right now, then the logical thing to do is to do your job well and make the best of it. As Martin Luther King said:
"If a man is called to be a street sweeper, he should sweep streets even as Michelangelo painted, or Beethoven composed music, or Shakespeare wrote poetry."
The problem here is that Dane's Cook character was not "called" to be a cashier. As we learn in the supermarket scene, he has a college degree, and fresh out of college created his own dot-com startup. Unfortunately, his dot-com business failed, as a result he lost all of his money and his family's money that was invested in it.
His reaction to this setback? He basically gave up on life and gave up on himself. So he stumbled into a job at the local mega-mart and, in order to sooth his ego, "dedicated" himself to the "art" of slacking--aka doing as little work as possible.
Zoom forward a few years... and we have the start of the movie. Zack is still slacking hard. Into the store walks Jessica Simpson (aka Amy), whose good looks and compatible personality motivate Zack to get off his slacking ass and go for employee of the month in order to get the girl.
All well and good. And of course at the end he wins the award and gets the girl. Fine. And then...
...nothing. The movie ends.
Huh? That's it? What about the dot-com? From the backstory it's clear Zack is wasting his talent and abilities as a cashier, something he never intrinsically cared about in the first place. (He only got motivated to go for cashier and employee of the month to impress the girl anyway, and gained a new sense of confidence and pride as a result.) Why doesn't he use his newfound motivation and newfound confidence to go for something he really wants in life--something that really suits him--like a new dot-com business, learning from the mistakes he made the first time? Why doesn't he use his victory as employee of the month as a stepping stone to future achievement?
THAT would have been a good end. That would have put the entire movie in perspective. That would have been both good comedy and good drama--both embracing the irony of the quest for "employee of the month" and transcending it.
And that would have made for a good movie.