Hollywood usually paints the successful businessman as the bad guy. Whether the film is located on Wall Street or in a suite of offices in Chicago, we often find ourselves booing the greedy guy who owns the business and rooting for his much less well-off employee. The plots may range from coming-of-age dramas, to physical comedies, to action films, but the popularity of the business villain definitely reveals something about the way our society views leadership and capitalism.

Bad Guy

With the cooler weather upon us, it may be time to hit up Netflix or your local video store to spend an evening or two getting reacquainted with some of the best – or worst, depending on your point of view – movie business villains. Here’s our list of the top five bad guys to get you started.

The top five bad guys

1. Gordon Gekko

played by Michael Douglas

Wall Street, 1987

directed by Oliver Stone

Michael Douglas earned an Oscar for Best Actor for his portrayal of corporate raider Gordon Gekko in Oliver Stone’s Wall Street. He reprised the role the 2010 sequel Wall Street: Money Never Sleeps.

Stone and co-screenwriter Stanley Weiser said at the time of the original film’s release that Gekko was loosely based on several actual investors, including Stone’s own father Louis Stone. The producer of the film Edward R. Pressman noted in an interview that while there was not one model for Gekko, he was partly based on Michael Milken, the American financier known developing of the market for high-yield bonds or “junk bonds” in the 1970s and 1980s.

Here’s an interesting side note: Forbes gave Gordon Gekko a net worth of $8.5 billion net worth and named him the fourth richest fictional character in 2008.

Although widely misquoted as saying “Greed is good” – partly due to a montage of scenes in trailers for the film – Gekko’s actual lines in the film about greed are:

“Greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through, and captures, the essence of the evolutionary spirit. Greed, in all of its forms; greed for life, for money, for love, knowledge, has marked the upward surge of mankind and greed, you mark my words, will not only save Teldar Paper, but that other malfunctioning corporation called the U.S.A.

2. Mr. Potter

played by Lionel Barrymore

It’s A Wonderful Life, 1946

directed by Frank Capra

Portrayed by veteran actor Lionel Barrymore, Henry F. Potter, or Mr. Potter as he is better known, has become almost as identifiable with miserliness as Charles Dickens’s Ebenezer Scrooge.

In Capra’s holiday classic, Potter is mill owner, banker and slumlord of Bedford Falls.  He will stop at nothing in his quest to bring about the downfall of Bailey Building & Loan, and its owner — the hero of the film — George Bailey (played by Jimmy Stewart). Our first glimpse of this villain is in his fine horse and buggy. When Clarence the angel asks “Who’s that, a king?”  his superior replies, “That’s Henry F. Potter, the richest and meanest man in the county.”

Here’s an example of why we love to hate Mr. Potter. He says these lines to George near the end of the film:

Look at you. You used to be so cocky. You were going to go out and conquer the world! You once called me a warped, frustrated, old man. What are you but a warped, frustrated young man? A miserable little clerk, crawling in here on your hands and knees and begging for help.

3. Blake

played by Alec Baldwin

Glengarry Glen Ross, 1992

directed by James Foley

David Mamet adapted his Pulitzer Prize and Tony winning play for the screen and gave us one of the best bad guy business monologues for the character of Blake.

Glengarry Glen Ross tells the story of two days in the lives of four real estate salesmen that includes their experience with a “trainer” the owners of the firm sent to motivate them.  Known for Mamet’s creative and frequent use of profanity, the film shows how desperate the men become when the trainer (Baldwin’s Blake character) announces that by the end of one week, all but the top two salesmen will be fired.

Here is part of Blake’s blistering “motivational” speech:

AB-C. A-always, B-be, C-closing. Always be closing! Always be closing!! A-I-D-A. Attention, interest, decision, action. Attention — do I have your attention? Interest — are you interested? I know you are because it’s **** or walk. You close or you hit the bricks! Decision — have you made your decision for Christ?!! And action. A-I-D-A; get out there!! You got the prospects comin’ in; you think they came in to get out of the rain? Guy doesn’t walk on the lot unless he wants to buy. Sitting out there waiting to give you their money! Are you gonna take it? Are you man enough to take it?

4. Charles Foster Kane

played by Orson Welles

Citizen Kane, 1941

directed by Orson Welles

Considered by some critics to be the greatest film ever made, Citizen Kane was directed, co-written, and produced by it star, Orson Welles. The story examines the life of newspaper magnate Charles Foster Kane, a character loosely based upon William Randolph Hearst and certain aspects of Welles’s own life.

Enormously wealthy at the time of his death, Kane has been living alone in a spacious estate with a “No Trespassing” sign on the gate. He dies after uttering the mysterious last word of “Rosebud.” Through the use of flashbacks – an innovative technique at the time – we learn the details of Kane’s life and legacy.

Here are two tastes of what Kane is made of:

You’re right; I did lose a million dollars last year. I expect to lose a million dollars this year. I expect to lose a million dollars next year. You know, Mr. Thatcher, at the rate of a million dollars a year, I’ll have to close this place in… 60 years.

As Charles Foster Kane who owns eighty-two thousand, six hundred and thirty-four shares of public transit – you see, I do have a general idea of my holdings – I sympathize with you. Charles Foster Kane is a scoundrel. His paper should be run out of town. A committee should be formed to boycott him. You may, if you can form such a committee, put me down for a contribution of one thousand dollars.

5. The Duke Brothers

played by Ralph Bellamy and Don Ameche

Trading Places, 1983

directed by John Landis

Starring Dan Aykroyd and Eddie Murphy, Trading Places is a Wall Street-style take on Mark Twain’s The Prince and the Pauper. The film tells the story of a commodities broker and a conman who are part of an elaborate bet by the two wealthy brothers who

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