This week's re-release of Oliver Stone's Wall Street on DVD (a precurser to the upcoming sequel, Wall Street: Money Never Sleeps, slated for September) serves to remind of us of one of cinema's great businessmen: Gordon Gekko, played with smarmy avarice by Michael Douglas.

There have been a lot of great businessman characters throughout the history of film. Some sneaky, some sincere, some completely off their rocker. Here are a few favorites.

C.C. Baxter and Jeff Sheldrake, The Apartment
Jack Lemmon's struggling, miserable clerk Baxter will do anything to get ahead -- including loaning his apartment to his married bosses for afternoon trysts. What seems like merely a bad idea becomes a nightmare when he finds out that his married boss Sheldrake (Fred MacMurray) is making time with the elevator girl (Shirley MacLaine) that Baxter secretly adores. Billy Wilder's comedy has a weird, dark undercurrent of pain, and Lemmon's at his best here.
Bill Lumbergh,Office Space
Obviously. We've all worked for this guy, we've all hated his guts, and Gary Cole's dim-witted, inward-focused portrayal -- and his endless droning about TPS reports -- is as cringe-inducing as it is hilarious. Um ... yeah.

Everyone, Glengarry Glen Ross
Where to start? Alec Baldwin's 'Always. Be. Closing" lecture, Al Pacino's rant, Jack Lemmon's meltdown .. the cast of James Foley's 1992 adaptation of David Mamet's play is too great, and the dialogue too brilliant, to narrow down to any one character or moment. the leads are weak, coffee's for closers, and you must get them to sign on the line which is dotted.

Chris Varick, Boiler Room
If you don't think Vin Diesel can act, then you've never seen Boiler Room, about brokers at a small-time Long Island stock mill. Diesel plays Varick as successful, profane, bigoted and supremely confident, and he looks great in a suit.

Buddy Ackerman, Swimming with Sharks
Guy (Frank Whaley) begins his new job under Hollywood producer Buddy (Kevin Spacey) and discovers that his new boss is a monster. While the story's about Guy's rise at the studio and his act of revenge against Buddy, it's Spacey's show all the way. Always gifted when it comes to toxic, venom-laced insult, his take on the prototypical ego-crazed power monster is magnificent. And, we're told, not at all over the top compared to some real-life execs.

Ryan Bingham, Up in the Air
George Clooney is perfect as a man whose life is about his job, which is to fly around the country, firing people. To do his job well, Bingham's learned to pack perfectly (he gives motivational speeches that hinge on the metaphor of a light suitcase), never put down roots, and stay unattached. When his bosses threaten to change his job so that he'll be desk-bound, the frequent flier finds himself re-assessing everything ... and the results are both funny and sad.

Kenneth Lay and the corporate weasels, Enron: The Smartest Guys in the Room
A Greek tragedy about arrogance and deceit on a grand scale, Alex Gibney's documentary introduces us to the energy-company execs whose business was to create arcane, shady, complex deals intended make vast amounts of money however possible, creating a labyrinth of fraud that's simply mind-boggling. These real-life crooks made Gordon Gekko look like an amateur.
categories Cinematical