What?
There’s a business comedy from the very early 80s with Judge Rheinhold and lots of comedian cameos… I think Danny Devito plays an exec who jumps out of a window. The name escapes me.
Do you mean Head Office? Can’t forget Office Space, either.
[slight hijack]
I just connected up with a guy I mentored back in the day - I managed him at work and helped him get into Business School but we haven’t spoken in 8-10 years. Turns out he got involved in setting up an energy trading market in Dubai before the Big Meltdown. It got turned into a book and now Jake Gyllenhaal is optioned to play him in the movie. I think George Clooney should play the grizzled-but-thoughtful mentor in the movie, don’t you agree? 
Too weird.
[/slight hijack]
Local Hero, in a way.
**
The Insider**
Michael Clayton
Disclosure
Rogue Trader
What Women Want
Working Girl
Tucker: The Man and his Dream
In Good Company
Jerry McGuire
Erin Brockovich
The Aviator
Barbarians at the Gate
Profit
It’s a tv show, not a movie, but it fits all the other qualifications (and you mentioned The Office, which I’m not too familiar with, but I think that is a show). It’s also really awesome.
Ruthless People, perhaps? (Danny DeVito’s wife, played by Bette Midler, is kidnapped by Judge Reinhold and Helen Slater, who were owed money by Danny DeVito.)
Actually, looking at Judge Reinhold’s filmography in IMDB, I think you’re thinking of Head Office.
Funny that Fish Called Wanda is mentioned, which gets a :dubious:
But, the ‘sequel’ - Fierce Creatures - concerns business to a degree.
A little gem called the Efficiency Expert is also kinda about business.
Primer is also kinda about doing a startup. As much as any time travelling movie is, I suppose.
Along with the movie Capra self-plagiarized from to make it: American Madness, which concentrates even more on the running of a bank.
In American Madness, there’s a smart and beloved bank manager who believes that you trust people instead of looking always at the bottom line. But there’s a run on the bank. All looks dark, but the friends of the bank manager all chip in to raise the money to keep it solvent
The Big Store (sort of).
And only half a season of it was ever filmed.
There Will Be Blood
I see The Hudsucker Proxy has already been mentioned.
Some shady business deals are the crux of Chinatown.
Not all business is conducted in a boardroom.
Syriana is largely a business movie as well.
I think this is probably the most excellent movie for discussing of futures market/shortselling that you’ll ever get. The OJ futures cornering scene is one that it took me years of watching and a couple of Dope threads and a wiki to understand.
Once you do understand what they’re doing it makes you say “ahhhhhh” with new relish. (It’s probably one of the most complicated scenes ever filmed in a light comedy for a wide audience.)
Though the movie being 26 years old (damn, how did that happen?) I’ve no idea how much has changed since it was filmed.
Rollover
1981 Kris Kristofferson and Jane Fonda
Euro Dollar market manipulation
Not rated for quality or content by Mongo Ponton.
Crazy People, a Dudley Moore movie about an advertising agency exceutive who gets thrown in a mental institution for writing truthful ads (example, “Metamucil: We help you go to the toilet so you won’t get cancer and die.”). As it turns out, the other residents of the institution are very good at writing ad copy. 
Not sure if documentaries would be appreciated as much as fictinal movies, but Enron: The Smartest Guys in the Room is a great look at the company’s underhanded dealings, its failure, and its aftermath. Unlike other documentaries in my collection which focus on certain types of businesses-- Maxed Out on the credit card industry, Just for Kicks on athletic shoe manufacturers, and so on-- the Enron film follows a single company and its individual executives, the power struggles, etc. It’s also more focused on business drama than the others (which typically have a strong advocacy slant, or are as focused on the pop-culture impact of the industry as it is on the industry itself). It does have an obvious, understandable bias, of course; the film is based on Bethany McLean and Peter Elkind’s book, and Ms. McLean was a Fortune magazine writer who began to publicly question Enron’s shady accounting at a time that the company seemed to be doing no wrong.
A more lighthearted documentary is A League of Ordinary Gentlemen, which covers the purchase and attempted refurbishment of the then-moribund PBA professional bowling league. While much of the film focuses on the personalities being marketed by the league as it attempted to make a comeback, it’s an interesting behind-the-scenes look at the business of running a business on the brink of failure, the tensions between marketing and performance (what happens when the best player is the least dynamic personality?), and so on. Unfortunately, it doesn’t go into the pure business aspect in as much detail as I’d like; the executives’ story would be interesting even without the players.
Sorry! That’s the one I meant! My brainfart.
As I said in post 22.
Hmmm. Should I use my power of invisibility for good or evil?
Pirates of Silicon Valley hasn’t been mentioned yet. It’s basically about Apple vs Microsoft.