40 Movies Every Entrepreneur Should Watch

Staring at the screen wondering which film to watch for inspiration, motivation or just to kill an evening?

Not to worry, to save you the headache I’ll be providing forty entrepreneur movies that cover all aspects of business, ranging from leadership to determination, also including case studies (of what not to do).

If you’re like me and overly picky when deciding what to watch, randomly generate a number between 1 and 40 and watch away!

Although the title of this post is aimed at entrepreneurs, these movies also include films aimed at employees too, as these films also carry important lessons that be carried over into any business, as well as a likely throwback to how things might have been back in your 9 to 5 days.

40 Entrepreneur Movies You Need To Watch

It’s worth noting that this list is in no particular order and that I have not watched every single movie.

Although I’ve watched most of them there are a select few that I’m still yet to watch, for those they will have been added to the list based on the positive feedback I’ve received from fellow entrepreneurs.

I look forward to watching them as much as I’m sure you are! Without further ado, let’s dive into this list…

#1 // The Pursuit of Happyness

We start this list with the modern classic fronted by none other than Will Smith. The Fresh Price stars as Chris Gardner, a salesman that pinned all of his luck on ‘Bone Density Scanners’.

After failing to live up to expectations, his wife leaves him and their only child to pursue other options, whilst Chris does whatever it takes to take care of his child – which includes joining a 6-month unpaid internship.

“Hey. Don’t ever let somebody tell you… You can’t do something. Not even me. All right? …You got a dream… You gotta protect it. People can’t do somethin’ themselves, they wanna tell you you can’t do it. If you want somethin’, go get it. Period.”

Chris Gardner, The Pursuit of Happyness

#2 // The Social Network

There’s this small website that some people tend to use called Facebook, you might have heard of it.

Well if not then this movie is a great lesson of how Mark Zuckerburg, Facebook’s founder, created the social media platform and how he went on to become the 5th richest person in the world.

As entrepreneur movies go, The Social Network has it all beginning with the initial idea, testing, launch & expansion, not to mention back-stabbery too!

“You don’t even know what the thing is yet. How big it can get, how far it can go. This is no time to take your chips down. A million dollars isn’t cool, you know what’s cool? …A billion dollars.”

Sean Parker, The Social Network

#3 // Wall Street

Desperate to make it to the top, a young Bud Fox convinces the greedy, high-rolling corporate raider Gordon Gekko, to take him under his wing in return for illegal insider information on the stocks.

When the potential ramifications of Bud Fox’s actions steer too close to home, he starts to question his morality.

If you’re an entrepreneur with an interest in the financial market or investing, this would definitely be one of the movies that I would recommend watching.

“Stop going for the easy buck and start producing something with your life. Create, instead of living off the buying and selling of others.”

Carl Fox, Wall Street

#4 // The Founder

Owner of the world’s largest fast-food chain, McDonald’s, Ray Kroc wasn’t actually the founder of the company famous for their golden arches.

In fact, Mr Kroc was a failing salesman who stumbled upon the McDonald brothers when selling them milkshake mixers, he saw amazing potential in the brother’s “speedy system” restaurant and looked to franchise it all over America and beyond.

The is one of my favourite entrepreneur movies, I’ve watched it a few times already – even if it does trigger me in the end!

“I know what you’re thinking, how the heck does a fifty-two year-old, over the hill, milkshake machine salesman build a fast food empire with sixteen hundred restaurants and an annual revenue of seven hundred million dollar? One word: persistence.”

Ray Kroc, The Founder

#5 // Glengarry Glen Ross

If you want to understand what being a salesman can really be like, then look no further than the excellent Glengarry Glen Ross.

Jam-packed with a spectacular cast including Al Pacino, Kevin Spacey and Alec Baldwin, the plot revolves around four salesmen, three of which are really struggling (which is becoming quite a theme in this post), are told that the two salesmen with the least amount of sales at the end of the month will be fired.

“The good news is – you’re fired. The bad news is – you’ve got, all of you’ve got just one week to regain your jobs starting with tonight. Starting with tonight’s sit. Oh? Have I got your attention now? Good.”

Blake, Glengarry Glen Ross

#6 // Becoming Warren Buffett

A feature-length documentary about Warren Buffett?

Ermm… Yes, please.

Of all the movies on this list, this one might be of the most useful to you as an entrepreneur – purely because of Warren’s wisdom and generosity.

Buffett made his seventy-billion dollar fortune from many shrewd investments, often searching for undervalued businesses with great potential. In many cases, Warren would leave the respective management teams to run their business as they had been prior to his investment.

One of Warren’s most notable investments would be when he, on behalf of his investment company Berkshire Hathaway, bought over one billion shares of Coca-Cola in 1988.

It’s safe to say that he’s consumed his fair share of the product too!

“The important thing is to look for the job you would take if you didn’t need a job.”

Warren Buffett, Becoming Warren Buffett

#7 // Startup.com

This entry from 2001 follows two friends, Kaleil Isaza Tuzman and Tom Herman, who have dreamt of setting up their own dot com business together.

After a successful launch of their website govWorks.com, things start to turn sour as they face many obstacles one might encounter when starting up their own (online) business, including the threat of competition and a clash of ideas.

As an entrepreneur, this film gave me greater insight into the volatility of the dot com boom that I haven’t quite seen in other movies.

“He doesn’t trust me.”

Kaleil Isaza Tuzman, Startup.com

#8 // The Wolf of Wall Street

Sex, Drugs and Margot Robbie, The Wolf of Wall Street has it all.

Based on the true story of the corrupt stockbroker Jordan Belfort, the “Wolf” and his 250 plus employees were found unlawfully unloading worthless penny stocks on unsuspecting clients, whilst manipulating the stock markets for their own gain.

After 22 months in prison for his wrongdoing, Jordan seems to have turned his life around as he teaches budding entrepreneurs about the art of sales, amongst other things.

The Wolf even features on my list of Top 50 Entrepreneurs To Follow On Social Media!

“Let me tell you something. There’s no nobility in poverty. I’ve been a poor man, and I’ve been a rich man. And I choose rich every fucking time.”

Jordan Belfort, The Wolf of Wall Street

#9 // Catch Me If You Can

Sticking with Leonard DiCaprio for a second, Catch Me If You Can is a movie that shares the real-life story of a young Frank Abagnale Jr who, inspired by his father and his burdening debt to the IRS, had managed to fraudulently forge millions of dollars of cheques.

Whilst doing so, Frank had successfully posed as a Pan Am pilot, doctor and lawyer, all whilst endlessly evading the pursuit of the FBI.

“Two little mice fell in a bucket of cream. The first mouse quickly gave up and drowned. The second mouse, wouldn’t quit. He struggled so hard that eventually he churned that cream into butter and crawled out. Gentlemen, as of this moment, I am that second mouse.”

Frank Abagnale Sr, Catch Me If You Can

#10 // Steve Jobs

The billionaire owner of a tech company that didn’t know how to build the very computer he made his name on, despite being ousted from the very company that he founded with friend Steve Wozniak, there’s no doubt that Apple wouldn’t be anywhere near as big as they are had they not brought Jobs back in 1997.

If you can get past the fact that Michael Fassbender’s character shares a little visual likeness to Steve, aside from the last third of the film, then this is certainly one of the many movies that I would recommend to any aspiring entrepreneur.

“Musicians play their instruments. I play the orchestra.”

Steve Jobs, Steve Jobs

#11 // How To Get Ahead In Advertising

Tasked with the job of creating a slogan for revolutionary new pimple cream, Bagley’s stress takes its toll on his relationship and general health, eventually causing him to have a mental breakdown.

During his mental block and deterioration of health, Bagley develops a boil of his own on his shoulder, however, this boil starts to grow eyes, a mouth and eventually a moustache.

The boil is highly critical of the advertising industry and acts as an additional question of morality.

“Nobody in advertising wants to get rid of boils. They’re good little money-spinners. All we want to do is offer hope of getting rid them, and that’s where I’m blocked.”

Denis Dimbleby Bagley, How To Get Ahead In Advertising

#12 // The Big Short

This movie follows the stories of a handful of investors, going against the grain and betting it all against the housing market ahead of the financial crisis in the mid-to-late 2000s.

Aside from having a stellar cast, The Big Short does a great job in explaining exactly how the crash occurred, and also showed how greed can be short-lived, as some of the largest banks in the world soon came to realise.

“I have a feeling, in a few years people are going to be doing what they always do when the economy tanks. They will be blaming immigrants and poor people.”

Mark Baum, The Big Short

#13 // Margin Call

Sticking with the 2008 financial crisis, Margin Call follows the 24-hour journey of a respected Investment bank.

The bank itself is looking to downsize, and one unlucky employee happens to be the head of risk management, who before departing the building had passed on an unfinished project he was working on – with the message to “be careful”.

It’s soon revealed that the information on that hard drive would unveil the vulnerability of the American economy.

“There are three ways to make a living in this business: be first, be smarter, or cheat.”

John Tuld, Margin Call

#14 // Enron: The Smartest Guys In The Room

Here lies a documentary about Enron, the American energy company, and how poor & immoral decision-making led to its downfall.

Within the space of a month, Enron had lost $65 billion in assets and had to file for bankruptcy.

This film offers insight into how the corporate was built on fraudulent lies, and how its inevitable crash came about. It also touches on other aspects of Enron’s collapse, including redundancies & suicide.

“Oh I can’t help myself. You know what the difference between the state of California and Titanic? And this is being webcast, and I know I’m going to regret this – at least when the Titanic went down, the lights were on.”

Jeffrey Skilling, Enron: The Smartest Guys In The Room

#15 // Lord of War

Set in the 1980s, Ukrainian immigrant Yuri Orlov looks to make it big as he decides to become an arms dealer in Little Odessa.

After becoming a millionaire from selling weapons to local mobsters and international clients, Yuri soon questions the morality of his actions as he starts a family, all whilst being chased down by INTERPOL.

“There are over 550 million firearms in worldwide circulation. That’s one firearm for every twelve people on the planet. The only question is: How do we arm the other 11?”

Yuri Orlov, Lord of War

#16 // Moneyball

Did I mention that this list would include some sports-related entrepreneur movies too? Well, it does. Everybody loves an underdog.

Even though I’m not a baseball fan, I thoroughly enjoyed watching Bennett Miller’s Moneyball.

The premise of the movie revolves around the Oakland A’s General Manager, Billy Beane, as his team is being picked apart by the bigger teams draft, after the draft.

In an attempt to compete with the big boys with their limited budget, Beane employs a young statistician who convinces him that there are bargains to be made in the market – based on computer-generated statistics alone.

This moment of innovation was about to reshape the game of baseball forever.

“The problem we’re trying to solve is that there are rich teams, and there are poor teams. Then there’s 50 feet of crap. And then there’s us. It’s an unfair game.”

Billy Beane, Moneyball

#17 // Fyre

Ahhh, the greatest party that never happened. FYRE is a Netflix original documentary of the infamous festival that crashed and burned due to the fraudulent activity of its founder, Billy McFarland.

Within 48 hours of the initial promotion from models and rappers, the Barbados-based festival was rapidly sold out.

What was hyped up as a luxury festival, turned into an absolute train-wreck, as McFarland had been dramatically overselling the organiser’s financial situation and as a result, festival-goers were left underwhelmed with soaked mattresses & cheese on bread.

“You’re our wonderful gay leader and we need you to go down [to customs]. Will you suck d**k to fix this water problem?”

Bill McFarland [to Andy King], Fyre

#18 // Pirates of Silicon Valley

This biographical film depicts the journeys of both Apple and Microsoft, as pioneers of digital technology.

The film digs deep into the lives of Steve Jobs, Steve Wozniak, Bill Gates & Steve Ballmer, as we take a look at their lives during college, how both companies were founded and how they both progressed into the absolute powerhouses that they are today.

Today being 1999 of course.

“Good artists copy, great artists steal.”

Steve Jobs, Pirates of Silicon Valley

#19 // Erin Brockovich

Single mother, Erin Brockovich, is desperate to find work in order to take care of her child. Her poor fortunes continue as she even loses a legal battle after she’d been struck by a car, as a result of the loss her lawyer is pressured into hiring Erin at his firm.

Despite being looked down on for her appearance & persona, Erin stumbles upon a large company that has been illegally dumping toxic waste & poisoning the surrounding areas.

With the go-ahead from her seniors, Erin finds herself being the cornerstone of what would be one of the biggest class-action lawsuits in American history.

“Now, I’m smart, I’m hard-working and I’ll do anything… and I’m not leaving here without a job.”

Erin Brockovich, Erin Brockovich

#20 // The Aviator

Centred around billionaire director and aviator Howard Hughes, this film looks at Hughes’ luxurious lifestyle, including flings with iconic ladies such as Katharine Hepburn and Ava Gardner.

Despite the entrepreneur directing huge movies and building a high-flying airline business, it wasn’t all fun and games for the aviator, as he regularly battled paralysing depression and phobias, which only grew in parallel to his success.

“You don’t care about money because you’ve always had it.”

Howard Hughes, The Aviator
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