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15 Gangster Movies Every Entrepreneur Should See and the Lessons They Teach

Miller's Crossing | 20th Century Fox

We're rebels in the United States. Literally. We live in country created by the most successful collection of rebels in world history, a group of elite intellectuals and tough-as-nails fighters who changed the direction of the world by defying the laws of a great empire.

So, it's not surprising a serious rebellious streak runs through the American psyche. It also explains our long-running fascination with pirates, bandits, outlaws and, of course, gangsters.

Gangsters became such a fascination in the early 20th century that Hollywood, always looking for a new trend, jumped on it with gusto. They haven't stopped since. Some of the most memorable films of all time come from this genre, which touch on so many factors that make up America, including an entrepreneurial spirit.

Of course, the entrepreneurs in these cases work outside the law, which is not advisable (a point all of these movies make, usually). But in watching these movies from the perspective of a business owner, each offers a lesson we could all do well to remember.

Take business classes to learn finance, management and data analysis. Watch these movies to have certain basic rules illustrated in every colorful way.

And be warned: we can't avoid a few spoilers.

Reservoir Dogs

15. Reservoir Dogs

The Lesson: Be professional

This film – Quentin Tarantino's first and still one of his best – represents the pinnacle of "heists gone wrong" films, with six people (all code named by colors), a mob boss and his son all caught up in a web of lies. And then there's Mr. Pink (Steve Buschemi).

As the gang's plans unravel, and people make mistakes and things get personal, it is Mr. Pink who tries to keep things on track. At one point, he beseeches the others: "Come on, guys, nobody wants this. We're supposed to be professionals!" Which is not a bad line to remember the next time things start going off the track in your business. Stay cool, stay professional. It's also worth noting that Mr. Pink comes out the best in the movie.

Miller’s Crossing

14. Miller’s Crossing

The Lesson: Don't get in over your head

This remarkable film from the Coen Brothers (borrowing heavily from Dashiell Hammett's "The Glass Key") focuses on Depression-era gangsters and features some of the sharpest, wittiest dialogue ever offered in a gangster movie. And while we could go on and on about the amazing performances from Albert Finney and Gabriel Byrne, for our purposes here we focus on the pivotal character of Bernie Bernbaum (John Turturro).

A small-time gangster, Bernie sets the wheels of the plot in motion when he tries to play with the big boys after one of them shows him mercy. His attempt to double-cross and blackmail a brilliant right-hand man of a mob boss leads to many complications and eventually his own undoing. Remember Bernie: find your niche and stick with it.

The Departed

13. The Departed

The Lesson: Information is power

Martin Scorsese has made many movies about gangsters, and this is one of his best. Scorcese's usual cinematic backdrop of New York is traded for Boston. Leonardo DiCaprio and Matt Damon play a police officer and mob member who have infiltrated the other side in an attempt to get valuable inside information. The whole movie is built around the idea of deception but also the importance of information, with devastating consequences for the people who lack it.

While it's not advisable to have spies working for your business – although Sun Tzu certainly thinks so – this movie provides scene after scene about the importance of having information and how it can lead to success. And how the lack of it can lead to failure.

In Bruges

12. In Bruges

The Lesson: It's never too late to change

In this dark comedy, two hitmen hide out in the city of Bruges, awaiting their fate after one of them, Ray (Colin Farrell), accidentally shot the wrong person on a job. His partner, Ken (Brendan Gleeson), has been told by his boss that he is going to have to kill Ray. That's the price for making a mistake as a hitman.

How Ken handles this order, and his behavior over the rest of the film, offers the savvy entrepreneur a good lesson in how changes sometimes have to be made when you find that previous decisions have put you on the wrong path. Admitting mistakes and changing course, rather than doggedly sticking out a path you laid in the past, is often a wise move.

Night Shift

11. Night Shift

The Lesson: Vet your ideas

Curveball! Night Shift is a comedy starring Michael Keaton and Henry Winkler as two guys who run a brothel out of a morgue. Not exactly gangsters, but they decide to work in the gangster arena, with predictably bad consequences. The main lesson for entrepreneurs: think through your ideas thoroughly before putting them into action. If it's not workable in theory, it definitely won't be in practice.

The film is also worth a mention because Keaton's character, Bill Blazejowski, is truly one of the most energetic entrepreneurs ever put onscreen, with scene after scene featuring the wild ideas that he puts into a tape recorder. A favorite: mix mayonnaise directly with the tuna in cans. Also, edible paper.


10. Scarface

The Lesson: If a deal sounds too good to be true…

Initially getting a mixed reaction upon its release in 1983 – mostly because of the stunning amount of violence – Scarface has become one of the most iconic of gangster movies. Al Pacino stars as Cuban immigrant turned drug lord Tony Montana. While he eventually succeeds, things don't start off very well.

In a pivotal scene early in the movie, a devious mob member offers Tony and his friends the chance to make a drug deal with Columbians. At the time they are working as dishwashers and jump at the chance to make real money. But things go very badly – when a chainsaw is part of a business meeting, that's not a good sign. Next time you are offered a seemingly perfect deal, think of Tony in that Miami hotel room. You might want to give it a second thought.

The Sopranos

9. The Sopranos

The Lesson: Separate the personal from the professional

OK, so it's not a movie, but did you think we'd get through this without mentioning Tony Soprano, the most iconic gangster in American fiction? Didn't think so. For six seasons on HBO, The Sopranos offered viewers a weekly glimpse into the travails of running a mob family, and plenty of lessons for business owners.

We'll focus on this one: never mix the personal with the professional. While that lesson is found in many gangster stories, nowhere is that more clear than with Tony Soprano (James Gandolfini), whose every problem typically starts with someone in his family causing disruption in his business (Uncle Junior, nephew Christopher, his own mother) and the occasional plot to kill him. While "family-owned business" is an American icon, you at least want to be extra careful about the family members you pick for business relationships. Or avoid them altogether.

Training Day

8. Training Day

The Lesson: Never pretend to be what you are not

Perhaps no other film on this list better shows the pitfalls of presenting yourself as something you are not – a serious mistake for any entrepreneur because honesty, discipline and integrity are the backbone of business.

Which brings us to Alonzo Harris (Denzel Washington), a decorated narcotics officer in the Los Angeles Police Department. He's also a gangster, using his position to scam, steal, bully and control crime, even over the gang members in his own neighborhood. Just watching Harris keep all the plates spinning is exhausting. How those plates come crashing down is a cautionary tale for anyone who thinks scamming and short cuts are the way to success.

American Gangster

7. American Gangster

The Lesson: Never let success go to your head

The temptation to show off your success is hard to resist. Rather than staying focused on your goals, you decide to let the world know you've "made it." That's hardly ever a wise move. No movie shows this better than a pivotal moment in this film, which stars Denzel Washington as Harlem gangster Frank Lucas and Russell Crowe as the police officer trying to bring him down.

The big moment comes at the "Fight of the Century," the epic 1971 boxing match between Joe Frazier and Muhammad Ali. Lucas, for years focused on his business and disciplined in keeping a low profile, shows up at the fight dressed in flashy clothes and with better seats than even the Italian mobsters. This gets him noticed by both the police and other criminal figures, and begins his long, messy downfall. Stay focused and disciplined. The only person who needs to know you've succeeded is you.

Gangs of New York

6. Gangs of New York

The Lesson: Business is not a zero sum game

Americans are a bit obsessed with winners and losers. There's a reason sayings such as "second place is really first last place" and "winning isn't everything, it's the only thing" (thanks, Vince Lombardi) are popular. But business is not a football game. For every winner, there does not have to be a loser.

Gangs of New York, yet another crime-centered movie by Martin Scorsese, is really a revenge film. Set primarily during the second year of the Civil War, it centers on a young man named Amsterdam (Leonardo DiCaprio) seeking to kill crime lord William Cutting (Daniel Day-Lewis) to avenge the death of his father. But the theme of beating the enemy and taking total control runs throughout the film, from Cutting's obsession with destroying immigrants to political battles at Tammany Hall.

All of these issues culminate in a chaotic final third of the film. An obsession with obliterating the enemy is not a path to success. Thinking otherwise will lead to people fighting to the death on the streets with knives and hatchets – metaphorically speaking, of course.

5. Casablanca

The Lesson: Keep an eye on current events

Usually this film falls on "most romantic" lists, but stick with us here. Everyone goes to Rick's in this classic film about an American running a nightclub in northern Africa during World War II. Played by Humphrey Bogart, Rick is not so much a gangster as an opportunistic entrepreneur, although he qualifies for this list because one of his "opportunities" is running an illegal gambling room in the back of his bar.

However, it all comes to screeching halt in a scene in which the French police decide to raid the club that previously had enjoyed protection – or at least indifference – from authorities. And the larger issue is that the Germans are moving into Africa, creating more potential governmental headaches for the crafty Rick.

While your business in unlikely to get raided by the police, it's good to stay on top of the political landscape and potential changes in law. You can only hope to handle it with the style that Rick manages.

4. Goodfellas

The Lesson: Don't over diversify

Goodfellas is based on the biography of Henry Hill, who worked for the mob for 25 years. There is a lot to like here, but a memorable lesson for entrepreneurs involves the pitfalls of spreading yourself too thin.

By the time the movie reaches its climatic moment, director Martin Scorsese chose to have a very long, very involved scene that brought all the loose threads of Henry's life into focus. Having long ago moved past the relatively simple nature of his robbery enterprise for the mob, Henry (Ray Liotta) spends a wild day balancing a gun deal, running his drug operation, getting his babysitter drug courier to the airport, avoiding a police helicopter and, of all things, making a spaghetti dinner.

It's a pivotal scene for entrepreneurs to keep in mind when they find themselves too diversified and not doing any one thing well.

3. Casino

The Lesson: Know what success looks like for you

Ask yourself what it is you really want out of business and life. Not just vague terms like "success" or short-term goals like increasing market share, but details on a true end goal. Not easy to answer? Unfortunately, a definitive idea of what success looks like is often a major gap in a small business plan.

One of the most interesting aspects of Casino is the interplay between partners Sam (Robert De Niro) and Nicky (Joe Pesci in full volatile mode). Sam knows what he wants. For him, running a profitable casino and elite status in Las Vegas is the goal. He gets joys simply running the casino as well as he possibly can, obsessed with every detail. He says: "Vegas was like a dream to me. Trouble was, Nicky was dreaming of his own kind of Vegas."

Nicky, the mob enforcer, never seems satisfied. Already successful, he starts defying both the law and mob orders by running his own side business that eventually causes everything to unravel. Needless to say it ends badly, especially for him. Knowing what you want, and what success looks like to you, is a powerful tool.

The Godfather Part II

2. The Godfather Part II

The Lesson: Know your business partners

Every day, there are stories about two businesses ending a relationship. Contracts are breached. Products are not up to quality. Deadlines are not met. Deliverables are not delivered.

If you want a vivid reminder of why to proceed very carefully in choosing a business partner, no better example exists than in The Godfather Part II (which could be subtitled: "More of the same, but better"). Here, Michael Corleone gets into a business deal with Hyman Roth (Lee Strasberg) that involves working with corrupt officials in the Cuban government. One major problem is that the government is about to be overthrown. An even worse problem is that Roth is actually plotting to kill Michael.

The Roth character shows not only the competitive ruthlessness of some business people but also how unscrupulous people will deliberately mislead you. You don't want someone like Roth on the other side of the table.

The Godfather

1. The Godfather

The Lesson: Surround yourself with Trustworthy, skilled people

One can argue that this film, which still finds its way on "best of" lists more than 40 years after its release, contains many valuable insights into American politics, business and even family life. But for our purposes here, this movie, better than any in all of filmdom, offers the perfect personification of the capable "right-hand man" in the character Tom Hagen (Robert Duvall).

The adopted brother of Michael Corleone (Al Pacino) proves invaluable in many ways. It's not just that he's loyal. It's also that he knows what he's doing. Witness how he deals with the Hollywood producer, for example. That's the sort of person you want in your inner circle. Almost everyone else betrays Michael, even people on his own team (leading one to say, when he is caught: "Tell Mike it was only business. I always liked him"). In a gangster movie this means a whole lot of people end up sleeping with the fishes, but in your life the most likely result is a failing business. Look for people like Tom.

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