Best:

Office Space
The most perfect workplace comedy in existence. TPS reports, efficiency experts, having to come in on Saturdays, cubicles, the weird guy who's weird about his stapler -- all of it resonates loud and clear with any and all office drones, not to mention the bonus digs at TGI Friday's-esque chain restaurants in the Aniston scenes.

9 to 5
It's like Office Space's mom, with the same immovable cubicle angst but with more boss kidnapping and cartoon fantasy sequences. Who hasn't fantasized about switching their evil boss's Skinny 'n Sweet with rat poison? It's perfectly natural.

Clockwatchers
The little indie, female-driven predecessor to Office Space, it never got quite as much enduring cult love, but Toni Collette, Parker Posey and Lisa Kudrow cooped up in the most boring office in the history of the world is great entertainment. And don't even get me started on that coffee collection cup woman. I've worked with dozens of her in real life.

Be Kind Rewind
Not a lot of people saw this, and though I do admit it's twee and sentimental as all hell, it's also undeniably charming and genuinely very funny. The workplace comedy genre in general tends to boil down to two main storylines: how working for corporate overlords sucks, or how being bought out by corporate overlords sucks. This is the latter, and aside from maybe Empire Records (which I only love for nostalgic, not objective, reasons), this is one of the most creative and effective movies of its kind.

The Devil Wears Prada
Everybody knows the fashion industry is a nightmare factory, but this movie managed to humanize the people working in it by seamlessly incorporating familiar Working Girl/Pretty Woman tropes. This movie focused more on the work aspect of the workplace genre than Working Girl did, which is why I'm including it in lieu of the Melanie Griffith classic, (which was really more of a romantic comedy), but the real reason Prada's amazing is that it actually had me rooting for Anna Wintour, something that seemed a sheer impossibility going in.

Anchorman
The weird thing about Anchorman? With all its over-the-top absurdity, working in local news really is kind of like this. Everybody who's ever held a job at a small radio or TV station seems to know a Brick Tamland. Or someone who's had to cover a cat fashion show, for that matter.

Clerks
Aside from the myriad other reasons Clerks is enjoyable, I've always found it particularly satisfying because everybody knows the worst shit always goes down on the days you're "not even supposed to be here."

Super Troopers
Arguably the Broken Lizard troupe's best work (though personally I still hold out for Beerfest being superior), Super Troopers is a cop movie solely about messing with civilians and hazing rookies, which is always the more entertaining side of police work, anyway. Because of this movie, I've been trying to get my TWoP colleagues to engage in maple syrup chugging contests since day one, to no avail. Maybe I should take up law enforcement.

Barbarians at the Gate
The movie that made Nabisco conference rooms look like the beaches of Normandy, and Wall Street look like Miss Congeniality. After watching an hour and a half of the gritty details of hostile takeovers, you kind of don't mind being a faceless pawn in a cubicle -- at least it's safe there.

Worst:

Waiting...
On paper, Waiting actually isn't that bad an idea. Food service employees are generally underpaid and treated like crap by the vast majority of customers, which results in a lot of health-code-violating vengeance. We all know this! We've all been there. And the cast, for the most part, is pretty inoffensive: Ryan Reynolds, Anna Faris, Justin Long, David Koechner, John Francis Daley, Chi McBride -- all funny people! The problem is Dane Cook. And Andy Milonakis. And the fact that you can only watch Dane Cook drop a steak on the floor and then laugh uproariously before serving it to someone so many times (zero times, really, is my personal threshold) before you can't help but hold it against the entire movie.

Barbershop
Here's the thing about Barbershop: I actually went into it thinking it could be funny, or at least have some funny parts. I don't know why I thought that, considering it starred Cedric the Entertainer and was written by the guy who penned Two Can Play That Game, but I did. So I paid to see it. And I honestly can't remember a time I was more wrong about a movie.

Paul Blart: Mall Cop
I know, I know -- we all know Paul Blart is the worst, and making fun of it isn't adding anything new to the discussion, but this depiction made me offended for security guards. Don't rent-a-cops get a bad enough rep without Kevin James getting dragged around an Orange Julius by some old man's Jazzy?

Your favorites? I considered adding Modern Times and His Girl Friday, but decided they were so self-evident it would be insulting or something. But that doesn't mean you can't talk about them! Go forth, and unleash the comment hounds!