Okay, I lied. This is actually a more specific list. It’s a list of movies about tycoons. However, since it’s safe to assume that no one ever searches for “tycoon movies,” I used a broader h1 header tag. (Please don’t tell Google.) By “tycoon” I mean guys who build empires. Call them deal-makers, if you prefer.

With the preamble out of the way, let’s get this show on the road.

The Top Ten Tycoon Movies

I’ve been a big film buff ever since I can remember and have a particular affection for good business movies. Unfortunately, good business movies are as rare as hen’s teeth. Tycoon movies are even scarcer. However, here is my top 10 list in no particular order:

Wall Street

Blue Horseshoe loves Anacott Steel!

I still love this movie after 10 or 15 viewings since its premiere in 1987. Sure it’s a morality play in the second half but the first half showing a young go-getter determined to land a big client is what entrepreneurship is all about. It’s about getting that first big sale by not taking “no” for an answer, even after 57 failed attempts. Few movies do a better job of showing what it’s like to suddenly have a lot of money coming in very quickly. Michael Douglas’s portrayal of corporate raider Gordon Gekko is one of the great performances in cinema, as far I’m concerned. Few scenes in film match the excitement of Bud Fox’s first meeting in Gekko’s office.

By the way, the tycoon in the film is Terence Stamp’s likeable character Sir Larry Wildman, not Gekko.

Sadly, the sequel was an unmitigated disaster. Shia LaBeouf? What was Oliver Stone smoking? The kid looks 14 years old in the movie–and still does. Call me old school, but if your little sister can pin a guy to the floor and take his lunch money, he is automatically disqualified from all leading man roles. Hollywood, please take note.

Other People’s Money

Other Peoples Money

Other People’s Money

This is a surprisingly good tycoon flick with Danny DeVito in the lead role. It came out in 1991, about four years after Wall Street, and fills in the details of how Gordon Gekko’s arch nemesis, tycoon Sir Larry Wildman, makes his money with public companies.

I mention Wall Street because OPM is a slightly odd combination of it and the 1960s Rock Hudson/Doris Day romantic comedies with DeVito as an improbable romantic lead. In the film he plays Wall Street raider Lawrence Garfield who launches a hostile take-over bid for a small public company, New England Wire & Cable, headed by Gregory Peck. Pay close attention to Garfield’s visit to NEW&C’s head office where he gives a chalkboard explanation on why he wants the company. It’s a great demonstration of how tycoons think. There are also two rousing speeches given in the shareholder meeting scene near the end of the film which argue both against and for the takeover tender. They are brilliantly written and delivered by Gregory Peck and De Vito, respectively.

This is another fine business movie I own a copy of for annual viewing. (I have to confess to not seeing it until about 2003 because it sounded silly.)

Lord of War

The first time you sell a gun is a lot like the first time you have sex. You have absolutely no idea what you’re doing but it is exciting and, in one way or another, it is over way too fast. – Yuri Orlov, Lord of War

Lord of War may well be the best exploration of the tycoon personality ever produced by Hollywood. In it Nicholas Cage plays the role of Yuri Orlov the son of a Ukrainian immigrant family operating a greasy spoon diner in Brighton Beach, New York. Yuri is bored stiff by the family business and longs for a more exciting and lucrative career. One day he spots an opportunity to get into the illegal arms trade business and quickly seizes it. He then embarks on a campaign to break into the major league of the international arms business after initially being rebuffed by one of its big boys. Fortunately for Yuri, he has an uncle who is a general in the Ukrainian army which is holding a fire sale on its Soviet supplied weapons systems after the collapse of the USSR. “Buy 6 helicopter gunships, and we throw in the 7th for free!”

This film does a superb job of portraying the emotional ups and downs and financial pressures of building a fast-growth business and leading the high-roller lifestyle in order to impress others. One very memorable scene is about all the expense and trouble Yuri goes to in order to finally meet the girl of his dreams. As you you watch it pay close attention to three key scenes where Yuri demonstrates his ability to remain calm and find a solution to a potential career-ending disaster. I refer to the three incidents where Ethan Hawke’s INTERPOL officer comes close to shutting Yuri down. (Yuri has great “confront.”)

Yuri is a prime example of the type of personality that tends to succeed in the big leagues. He has clear cut priorities and knows what things have to take a back seat to them. He is willing to make sacrifices in order to succeed.

If you listen closely, Yuri has a lot of quotable lines.

Don’t let the fact that Yuri is a weapons dealer turn you off. If that troubles you just pretend that he’s selling something like ice-cream. Regardless of the merchandise, it’s an authentic portrayal of a very ambitious and driven individual.

I’d love to have a sequel made about how Yuri continued building his empire, but it won’t happen.

The Man Who Would Be King

I can almost hear you asking, “The Man Who Would Be King? How is this a film about business?” If you don’t think that this is a movie about business and tycoons, you’re dead wrong, my friend. Indeed it’s a beautiful metaphor for both the tycoon mindset and growth strategy we cover in the Playbook.

Tycoon Tales: The Man Who Would Be King

Tycoon Tales: The Man Who Would Be King

Ex-British soldiers Daniel Dravot (Sean Connery) and Peachy Carnehan (Michael Caine) have big dreams after retiring from her majesty’s service. They want to take over one of the Central Asian kingdoms up in the Himalayas, northwest of India, and set themselves up as its rulers. However, they find themselves in typical startup circumstances with next to nothing in terms of funding. So in classic entrepreneurial fashion, the limited financial resources they do have are invested in assets which will bring them the biggest bang for the buck–literally: 16 Martini-Henry repeating rifles.

They then use these rifles to both impress and intimidate the thuggish ruler of a small autonomous tribe on the outskirts of their target country of Kafiristan. This first alliance then becomes the “platform company” from which they launch an M&A campaign to acquire control of additional tribes. Can you say “industry roll-up”? In quick succession, they acquire enough of these “assets” to take over the entire kingdom.

This is when their real problems begin due to hubris on the part of Daniel who ignores the warning signs and wants to remain as permanent monarch. In contrast, Peachy just wants to get out of Dodge with the loot before the bubble bursts—which it does very quickly.

The Hoax

The Hoax is one of my favorite films. It’s a caper flick and a buddy movie based on a true story all rolled into one! Does it get any better than that? Don’t think so. In it Richard Gere plays Clifford Irving the writer who in 1970 caused a national sensation by claiming that the elusive billionaire Howard Hughes had commissioned him to write the first ever authorized Hughes biography. The truth was that the two men had never communicated in any manner. The scam worked well enough for Irving to receive a one million dollar advance from a major publishing house, despite the fact that it never had any direct contact with Hughes to verify Irving’s claims. Everything was based on handwritten notes allegedly from Hughes, but in fact forged by Irving. Finally, Irving was able to present a manuscript which passed all the industry sniff tests before being published, including a handwriting analysis. The charade only collapsed when the eccentric Hughes finally came out of hiding to denounce the by then bestseller as a hoax.

The Hoax

Richard Gere and Alfred Molina in The Hoax

What’s particularly interesting about the film is how Irving relies on brinkmanship to save the day every time the universe is about to drop the hammer on him. If you study tycoons, you will see that they readily bet the farm in tough situations as opposed to the rest of us. Sometimes they win and sometimes they lose.

For the record, Irving spent a year in jail for his crime and had to repay his advance to the publisher, but lived to write many more books afterwards, including one about his great hoax, The Hoax.

This is one of Richard Gere’s best roles ever, but the wonderful Alfred Molina almost steals the film from him. Molina is an absolute blast as his insecure best friend Richard Suskind.

There Will Be Blood

This is one of PT Anderson’s finest works. In it Daniel Day Lewis plays a ruthless man driven to succeed. The story starts in 1898 with Daniel Plainview digging on his own for gold out in California. When his mine shaft floods with oil one day he switches his business model to oil drilling contractor. The story then follows his progress over the next three decades as he becomes a wealthy but lonely man along the lines of Citizen Kane. Be forewarned that it’s a dark movie.

The memorable opening sequence goes on for about 14 minutes before any dialogue is heard. The camera simply follows Plainview as he engages in leg-breaking work. Literally. At one point he breaks his leg in a fall and then crawls on his back into town to file a claim with the assay office.

There’s an iconic scene near the beginning where after a hard day of digging for gold Plainview sits out in the desert drinking coffee while planning and dreaming. You just know that nothing is going to stop him.

Click to embiggen.

Daniel Plainview

Daniel Plainview: a man with a plan.


Here’s another flick with Richard Gere playing a Wall Street tycoon attempting to unload his company before it collapses like a house of cards due to financial reporting improprieties. There’s also a secondary story about Gere’s character’s private life which is no where as riveting as the business story. No one plays wealthy businessmen better than Gere and Michael Douglas, although the latter has now lost his vigor due a combination of age and serious illness.

Warning: Do not watch the trailer as it gives the entire story line away.

The Aviator

Everyone has seen this one. Martin Scorsese directs Leo DiCaprio playing Howard Hughes. Hughes was the Elon Musk of his day, an absolutely brilliant engineer who came to a sad lonely end. I plan to do a major piece on how Hughes built his empire in the near future. His story is one of the great ones.

The Wolf of Wall Street

It’s the dynamic duo, Martin Scorsese and Leo DiCaprio, together again. From what I have read Martin really enjoys working with super nice guy Leo, and who can blame him for that? This film doesn’t come out for a few more months but looks promising. It’s based on a true story about a hustler, Jordan Belfort, who built one of the most notorious boiler rooms of the 1990s and served time for it later. Since he was taking companies public it meets my criterion of a deal-maker. A year or two ago, I tried reading the book but couldn’t finish it. It’s bad. But the movie trailer looks good.

The Men Who Built America

This is not a film but rather a four part History Channel series on the tycoons who built America in the 19th century: Cornelius Vanderbilt, John D. Rockefeller, J.P. Morgan, Andrew Carnegie, Henry Ford, and a few others. I am including it here because the series relies on dramatizations to tell their stories. There’s going to be a second season from what I hear.

If you have been counting, you already know that this is only nine films and not ten. Like I said, these types of films are rare, so give me credit for making it 90% of the way. If anyone knows of any other films about tycoon/deal-maker types that I missed, tell me.

By the way, I didn’t include Citizen Kane because I fell asleep the one time I tried watching it.

The end


18 Responses to Top Ten Business Movies

  • Great list! I have only seen three of them. We feel the same way about Shia LaBeouf.

  • Thanks for the heads up on the Richard Gere movies. He’s yummie.

  • just curious,

    why didn’t “Barbarians at the Gate” make the list?

    • Great list and yes Barbarians at the Gate was awesome for the purposes of this list. As a huge Garner, Douglas, and Gere fan I loved all of their movies mentioned here. My small company is affiliated with KKR so B@TG was particularly interesting. Be on the lookout for a book written by Joe Plumeri coming out in 2015, one of the greatest tycoons alive today. In my humble opinion, you have to have that warped type of personality who can watch these movies over and over or read the books and be thoroughly entertained. My wife always asks “how can you find all those movies and books on business and sales so entertaining?” What can I say? I just do. People like us seem to be wired just a little different from the rest of the world. Great info. Thanks!

  • Good point. It should be on the list. My bad.

  • Check out Middle Men

  • Pirates of Silicon Valley is also worth seeing. It’s an old TNT TV film about the birth of the PC industry and the rivalry between Apple and Microsoft.

    • Hi Rich,

      although it’s a good movie, I am not sure if that would fit this genre of movies nor the Tycoon philosophy.

  • very impressive, why there’s no “the smartest guys in the room” in your list ?

    • @Suri,

      the list is very specific. It’s not a list about “Corporate Movies”. It’s very specific to deal guys. Guys that are involved with doing deals at the highest levels. Enron is another animal.

  • Thanks for the list Peter! I have seen some of them, and looking forward to seeing the rest and rewatching others again.

  • Peter, I am really enjoying your writing and found this movie list very beneficial. Are you familiar with Australian tycoons such as the Packers? The Packer dynasty is now on the third generation. This month a two part mini-series aired on the Packers and their media war with Rupert Murdoch in the 1960s and 1970s. You might enjoy it if you try it.

    Power Games: The Packer-Murdoch Story


  • Hank, yes I do know about the Packers. I read about the great newspaper war that Rupert launched against them in one of his biographies. I’ll keep a look out for that miniseries. Thanks.

  • Loved Michael Douglas as Gordon Gekko in Wall Street! Although the next two are not movies about business tycoons, my former business students loved the “Boiler Room” with Vin Diesel and Giovanni Ribisi and “Glengarry Glen Ross” with Al Pacino, Ed Harris and Kevin Spacey. I can think of no other film that conveys the stress of being in commission sales like Glengarry Glen Ross does.

  • You missed an old classic about a real hustler. The Apprenticeship of Duddy Kravitz. This belongs on your list.

  • The Thomas Crown Affair.
    Great tycoon film!

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