Movies about business tend to be of two kinds: inspirational stories of overcoming setbacks and struggles, and cautionary tales of corruption and failure. Of the two, there are a LOT more of the second. Let’s face it: stories about functional businesses – where management is practical and smart, employees are respected and valued, and customers are satisfied and loyal – don’t exactly deliver the drama that we want out of a movie.

That doesn’t mean a business-person can’t learn a lot from the movies, though – just that you can learn more about what not to do than what to do. After all, learning what to do is what business school is for. Learning what not to do is entertainment. With that in mind, here are our picks for the best business movies of all time.

1. Wall Street: Money Never Sleeps (2010)

source
Film critics would argue that the first Wall Street – the one that launched a million careers in investment banking and brought “Greed is good” into our language – should be first on the list. No doubt, it’s a classic: Michael Douglas’ effortless cool and way of wearing a tailored suit shaped the look of the real Wall Street for over twenty years. In Wall Street (1987), Gordon Gekko (Michael Douglas) is so slick and compelling a con man that nearly everyone who saw the film forgot he was the villain; he robs and pillages without an ounce of conscience or compassion. But that’s exactly why the sequel is on this list.

Wall Street: Money Never Sleeps, on the other hand, shows the human, social, and cultural cost of Gekko-style profiteering, as Gekko is released from prison with eight years of his life lost, tries in vain to warn Wall Street of impending disaster, and finds himself back in the game after the 2008 economic collapse, mopping up all the spilled money. The lure of fast, ill-gotten fortune briefly overcomes Gekko again, and nearly ends his relationship with his estranged daughter forever, but in the end what sticks with the audience is writer/director Oliver Stone’s vision of a world not just corrupted by greed, but devastated by it. But this time, Gordon Gekko is the voice of reason.

2. The Godfather (1972)

source
The Godfather is a lot of things: family drama, gangster thriller, period piece, and the best advertisement for cannoli the cinema ever produced. It also invented the term “badda-bing,” for which Mafia wanna-bes will forever be grateful. But The Godfather is also an exemplary guide to business. We all know the pull-quotes: “I’ll make him an offer he can’t refuse;” “It’s business, not personal;” “Never tell anyone outside the family what you’re thinking;” “Don’t ever take sides with anyone against the family;” “He’s thinking of going to the mattresses.”

So, it’s probably not a good idea to send messages via horse-head in a legitimate business. But many of the other lessons of The Godfather are entirely applicable: knowing the difference between ambition and over-reaching, for instance; knowing who to trust; learning when to be loyal and when to jump a sinking ship; knowing your clientele and your product; getting your hands dirty without selling your soul; and, above all, leading wisely, boldly, and steadily. If Sonny had known these principles like Michael, the movie would have a very different ending. Maybe not as dramatic, but certainly less bloody.

3. Glengarry Glen Ross (1992)

source
Sales is hard. There are plenty of movies, novels, and plays about just how hard, most famously Death of a Salesman, but nothing quite captures the rugged, outsized confidence of a successful salesman, or the pitiful desperation of a failed one, like David Mamet’s Glengarry Glen Ross. In Glengarry Glen Ross, a “motivator” from the head office visits a regional real estate office to deliver a message from management: the two lowest sales for the week will be fired.

Like Wall Street, Glengarry Glen Ross is mostly revered for the wrong reasons, particularly Alec Baldwin’s brief, profane, show-stopping monologue in the first act. True, it’s got some pretty good advice: “ABC – Always Be Closing,” he tells the salesmen. But it’s all predicated on a very bad business plan – pit everyone in the office against each other in a brutal, winner-take-all competition. Or, as Baldwin’s character puts it, “Second prize is a set of steak knives. Third prize is, you’re fired.” This vicious mandate from management drives an already underhanded business with shaky ethics to outright corruption, as some of the salesmen bribe, threaten, and intimidate each other, and others plot a break-in and theft of the most valuable leads. It’s an important lesson for anyone who intends to own or manage a business – no-holds-barred competition may get results, but within a business, it’s toxic. An office that can’t cooperate will crumble.

4. Boiler Room (2000)

source
Boiler Room is like the love child of Wall Street and Glengarry Glen Ross, a seductive look at the seediest side of Wall Street. At J.T. Marlin, a “pump and dump” firm that artificially inflates the stock prices of failing businesses, unscrupulous young brokers make a fortune hard-selling overpriced stocks to investors, knowing the businesses are already dead. And as with Wall Street and Glengarry Glen Ross, Boiler Room has become something of a cult classic, and unlikely business guide. With its cast of good-looking, ridiculously charismatic stars (the cream of 2000’s crop of young actors, including Ben Affleck, Giovanni Ribisi, and Vin Diesel in a role that nearly made him a serious star), Boiler Room makes this unethical world as romantic to the viewer as it is to Ribisi’s neophyte protagonist.

But like many business movies, Boiler Room is above all a cautionary tale of greed and corruption. Ribisi’ character, Seth Davis, has a crisis of conscience when his advice causes financial and personal ruin for an ordinary family man who is trying to buy a new house. But his Jiminy Cricket isn’t quite enough to change his mind about the firm until he’s caught by the FBI and offered an immunity deal. Boiler Room doesn’t show us what happens to the other brokers, but the paddy wagons and police cars don’t bode well. Another rule of business learned from the movie: fast money is probably dirty money.

5. The Social Network (2010)

source
David Fincher’s The Social Network – written by hyperverbalist Aaron Sorkin – has been criticized for its historical inaccuracies and unflattering depiction of Facebook founder Mark Zuckerberg. To which film lovers say, “So?” It’s the only film ever to make endless talk about programming, ownership percentages, and intellectual property look and sound like a thriller. Mark Zuckerberg may not be the socially-inept, heartless misogynist Jesse Eisenberg portrays, but, as the tagline reads, you don’t get to 500 million friends without making a few enemies. Unfortunately, the enemies Zuckerberg makes,according to the film, are the friends who helped get him there.

The Social Network is not a guide to becoming a billionaire – the success of Facebook is presented as a combination of genius, luck, and ruthless opportunism. So maybe it is a guide to becoming a billionaire. But that success comes at a cost for Zuckerberg, as he is successfully sued by his former partner/best friend, and by the trust-fund frat boys who gave him the idea in the first place. Zuckerberg is left, in an instantly classic scene, alone at his computer, refreshing the page, hoping for a friend confirmation. For you business majors, lesson to be gained: don’t forget the ones who help you succeed, and don’t cheat those who are loyal to you.

6. Citizen Kane (1941)

source
The greatest American film in history is also one of the best business films in history. A heavily fictionalized – more loosely inspired – biopic of William Randolph Hearst, writer, director, and star Orson Welles plays Charles Foster Kane, who rises from poverty (via the discovery of a gold mine on his family’s property) to enormous wealth and power. As a young newspaper tycoon, Kane has enough influence to scare up a war with Spain and almost elect himself governor. But from that height, of course, comes a fall. Not in wealth – he dies richer than ever – but in his humanity.

Welle’s portrayal of Kane is monumental – a man of raging ambitions, uncontrollable appetites, and insidious charm. Like Gordon Gekko, he’s one of the slimiest, yet most irresistably charismatic, protagonists in American film. And Welles uses every element of the medium, from the high-contrast, deep-focus cinematography to the music (“It can’t be love, because there is no true love”), to make Kane’s emotional and psychological devastation as relatable, pitiable, and plausible as possible. At a human level, Citizen Kane reminds business people to remember the people at home. All the wealth in the world can’t buy love.

7. The Apartment (1960)

source
One of writer-director Billy Wilder’s incredible string of hits in the 50s and 60s, The Apartment was controversial in its day for its frank depiction of infidelity. Jack Lemmon (who makes this list twice as a star of Glengarry Glen Ross) plays C.C. Baxter, a lonely office worker for a New York insurance company. Weak-willed and unambitious, Baxter allows company executives to use his apartment for meetings with their mistresses, in return for good personnel reports. When the personnel director catches on to the scheme, he blackmails Baxter for exclusive apartment priveleges – with his mistress, Miss Kubelik, the object of Baxter’s affection.

Being a romantic comedy, love eventually wins out in The Apartment, but what sticks with viewers is the absurd humor and man-in-the-grey-flannel-suit-era office politics. Characters speak unironically in 50s corporate cliches, including attaching “-wise” to the end of any word to make it an adjective, and clearly it will be a long time before any of the characters learn the term “sexual harrassment.” But as a story of bosses who ask too much, and employees who give too much, The Apartment will stay relevant for a long, long time.

8. Office Space (1999)

source

Office Space has a simple lesson for businesspeople: embezzlement is fun. Wait, that can’t be right. A flop when it was first released (writer-director Mike Judge complained that it was poorly marketed), video and DVD made it a cult classic among IT workers and other frustrated rank-and-file office drones. This dark comedy tapped into a deep well of resentment at the heart of the 90s tech-powered economic boom – all of those young professionals who did everything “right” (going to college, choosing a practical, stable job, working hard) and found themselves trapped in cubicles with managers who had no idea how to motivate them or even what they did.

Think of it as Dilbert with guts. Three computer programmers, inspired by the silly plot of Superman III, hatch a scheme to embezzle fractions of a cent from each transaction the company makes, building a fortune slowly enough that the company will never notice. A misplaced decimal point gets them hundreds of thousands in a few hours. But it’s not the story that captured the movie’s fans so much as the many scenes of wish-fulfillment – speaking your mind to the boss, goofing off with impunity, and (most vividly and memorably) taking a baseball bat to a chronically malfunctioning printer. Let Office Space stand as a warning to managers: taking the time to get to know your employees, learn their jobs and skills, and communicate with them about their needs, will make a happier, more productive, and less-likely-to-be-burned-down workplace.