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25 best business movies: 1-5

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5. Double Indemnity (1944)

Starring Fred MacMurrayBarbara StanwyckEdward G. Robinson 

Directed by Billy Wilder 

What it’s about: Phyllis Dietrichson (Barbara Stanwyck) doesn’t like her husband. I mean, she really doesn’t like him, and enlists the services of Walter Neff (Fred MacMurray), the top salesman at the Pacific All Risk Insurance Co., to help carry out the perfect crime.

Why watch it: Well, a few years back, the American Film Institute ranked Double Indemnity as the No. 29 greatest movie of all time. In addition, Stanwyck gives one of the silver screen’s great villainous performances. Stanwyck’s baddie is not the over-the-top type we’re used to these days. Hers is a slow, slow burn that is both subtle and cruel in its execution. 

Business takeaway: Check the fine print on your insurance policies or any legal document before you sign them. You never know what you might find in there. 

Memorable scene: When Phyllis and Walter meet for the first time, the double entendres erupt like machine gun fire. It’s both seductive and dangerous and sets the tone for the rest of the movie.

Memorable quotes: 

Barton Keyes: Well, I get darn sick of trying to pick up after a gang of fast-talking salesmen dumb enough to sell life insurance to a guy who sleeps in the same bed with four rattlesnakes. 

Barton Keyes: But it isn’t twice as safe. It’s 10 times twice as dangerous. They’ve committed a *murder*! And it’s not like taking a trolley ride together where they can get off at different stops. They’re stuck with each other and they got to ride all the way to the end of the line and it’s a one-way trip and the last stop is the cemetery.

Walter Neff: I was thinking about that dame upstairs, and the way she had looked at me, and I wanted to see her again, close, without that silly staircase between us. 

Walter Neff: Yes, I killed him. I killed him for money — and a woman — and I didn’t get the money and I didn’t get the woman. Pretty, isn’t it? 

Next up: Up in the Air

4. Up in the Air (2009)

Starring George Clooney, Vera Farmiga

Directed by Jason Reitman

What it’s about: George Clooney plays a corporate headhunter who lives out of a suitcase, traveling the country to fire people whose bosses don’t have the cojones to do it themselves. In fact, in the previous year alone Ryan Bingham (Clooney) spent 322 days on the road and “43 miserable days at home.” His goal is to achieve 10 million miles flown, a feat reached by only six other people.

Why watch it: The film provides keen insight into the frequent business traveler, and also addresses the brutality of corporate downsizing.

Business takeaway: If you’re going to live out of a suitcase — or, in Bingham’s metaphor for life, a backpack — you have to realize the strain it will put on any personal attachments you have.

Memorable scenes: The montage of how efficient Bingham is when he travels is a marvel of minimalism. Also, the IT conference party he crashes accurately cuts to the bone with its shuffling dance floor and karaoke set up.

Memorable quotes: 

Bingham: To know me is to fly with me. This is where I live.

Bingham: Stuff your life in a backpack then try to walk. We weigh ourselves down until we can’t even move.

Bingham: (on reaching 10 million miles.) I’d be the seventh person to do it. More people have walked on the moon. 

Next up: Citizen Kane

3. Citizen Kane (1941)

Starring Orson WellesJoseph CottenDorothy Comingore

Directed by Orson Welles

What’s it about: Based loosely on the rise of newspaper tycoon William Randolph Hearst, Citizen Kane is about the life and lost innocence of Charles Foster Kane (played by the then 25-year-old Orson Welles, who also directed and co-wrote this cinematic epic). Welles later denied that the film was only about Hearst, saying it was instead a composite of industry barons of that era.

Why watch it: The American Film Institute ranked the film the greatest American movie of all time in 1998, and again in 2007. Its impact and influence on movies is indisputable. The use of camera angles, lighting and depth of focus are studied in film schools and emulated in films to this day. If I were judging it merely as a movie, it would be higher on this list. But I’m looking at it from its impact on business.

Business takeaway: Power corrupts. Greed, for lack of a better word, is not good.

Memorable scene: The opening with Kane (Welles) uttering the single word, “Rosebud” and allowing the snow globe to roll from his hand and crash to the floor.

Memorable quotes: 

Charles Foster Kane: Rosebud.

Thompson: No, I don’t think so; no. Mr. Kane was a man who got everything he wanted and then lost it. Maybe Rosebud was something he couldn’t get, or something he lost. Anyway, it wouldn’t have explained anything … I don’t think any word can explain a man’s life. No, I guess Rosebud is just a … piece in a jigsaw puzzle … a missing piece.


Bernstein: Old age. It’s the only disease, Mr. Thompson, that you don’t look forward to being cured of. 


Charles Foster Kane: You know, Mr. Bernstein, if I hadn’t been very rich, I might have been a really great man.

Next up: Glengarry Glen Ross


2. Glengarry Glen Ross (1992)

starring Al PacinoJack LemmonAlec BaldwinAlan ArkinEd HarrisKevin SpaceyJonathan Pryce

Directed by James Foley

What’s it about: The intense pressure mounting on a beleaguered small Chicago real estate office.

Why watch it: The definitive sales movie. The badgering, inspirational speech that Blake (Alec Baldwin) gives the disgruntled sales team.

Business takeaways: ABC. Always be closing. It’s all about the leads.

Memorable scene: When James Lingk (Jonathan Pryce) comes to the real estate office with buyer’s remorse, Ricky Roma (Al Pacino) continues to run the con on him.

Memorable quotes: 

Blake: These are the new leads. These are the Glengarry leads. And to you they’re gold, and you don’t get them. Why? Because to give them to you would be throwing them away. They’re for closers. 

Blake: We’re adding a little something to this month’s sales contest. As you all know, first prize is a Cadillac Eldorado. Anybody want to see second prize? Second prize is a set of steak knives. Third prize is you’re fired. 

Blake: A-B-C. A-Always, B-Be, C-Closing. Always be closing, always be closing. 

Next up: The Godfather

1. The Godfather (1972)

Starring Marlon Brando, Al Pacino, James Caan, Robert Duvall, Diane Keaton

Directed by Francis Ford Coppola

What it’s about: The transfer of power from the aging leader of an organized crime family to his reluctant son and the fight for absolute power that unfolds.

Why watch it: You’ve most likely seen it, but have you ever watched it as a meditation on business strategy? Take the plunge and give it another shot.

Business takeaway: The art of negotiation, i.e. “I’ll make you an offer you can’t refuse.” The blood of family is thicker than water.

Memorable scene: The director waking up with one of his prized possessions in bed with him. Also, the opening where Don Corleone (Marlon Brando) sits with a cat in his lap, listening to people who come to him asking favors.

Memorable quotes:

Don Corleone: I’m gonna make him an offer he won’t refuse.

Don Corleone: [to Michael] Listen, whoever comes to you with this Barzini meeting, he’s the traitor. Don’t forget that.

Emilio Barzini: [during a meeting with the Five Families] Times have changed. It’s not like the Old Days, when we can do anything we want. A refusal is not the act of a friend. If Don Corleone had all the judges, and the politicians in New York, then he must share them, or let us others use them. He must let us draw the water from the well. Certainly he can present a bill for such services; after all … we are not Communists.

Luca Brasi: Don Corleone, I am honored and grateful that you have invited me to your home on the wedding day of your daughter. And may their first child be a masculine child.

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