The 8 Best Entrepreneur Movies of 2020

Before you become a head-honcho, watch these flicks

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People become entrepreneurs for many reasons. For some, it’s because they have a genius and all-consuming idea that they just have to see through. Others are motivated by greed, revenge or just a desire to escape the office grind. But regardless of whether or not you personally aspire to be your own boss, the impact that entrepreneurs have on the future, our shared past and the world all around us is worth learning from. In a small company where the stakes are high, the best and worst impulses of humanity are often brought to the surface – making entrepreneurs and their teams all that much easier to learn from. So we put together a list of the best entrepreneur movies to watch this year to fast-track your inner Steve Jobs or Oprah Winfrey dreams.

Best for Aspiring Media Moguls:

Most people who are starting a business are way too busy with the day-to-day operations to document their every move. Not so with the founders of, who this documentary follows. The media industry is constantly evolving and new media startups come and go. is one of those that came – and eventually met its demise. This movie follows the rise and fall of the ambitious fledgling company and its founders. You’ll learn the pitfalls of the ever-enticing, venture-capital-backed funding method and the real-life main characters will help you appreciate just how difficult starting a company can be.

Best On Tech: Pirates of Silicon Valley

Pirates of Silicon Valley
 Courtesy of Amazon

Sleek metal, rounded edges and a glowing white fruit with a bite taken out of it are all hallmarks of Apple today – but it wasn’t always that way. And don’t forget Microsoft, the company that introduced the world to the integrated office suite used around the world today – including on Apple computers. This movie follows the lives of Apple co-founder Steve Jobs, played by Noah Wyle, and Microsoft founder Bill Gates, played by Anthony Michael Hall. Throughout the film, you’ll get to see just how fierce, and nerdy, the tech revolution and the battle to create the best personal computer really was. Gates is more concerned about the technical aspects of building the perfect machines, while Jobs wants to “create the new consciousness” through his work. Who’s ideology will prevail? Well, that’s still yet to be seen.

Best Feel Good Film: The Pursuit Of Happyness

The American dream is based on building yourself up through your own ingenuity from even the lowliest of circumstances and this film is a perfect example of just how hard accomplishing that can sometimes be – and how much you can accomplish with a little luck and a ton of hard work. In this movie based on the true story of homeless-man-turned-multi-millionaire, Chris Gardner, Will Smith plays a struggling salesman who ends up becoming homeless due to an unhappy accident – and changing his own life through an encounter of fate. Gardner, despite living out of a subway station restroom with his son, manages to hold down an unpaid internship at a competitive firm and ends up securing a coveted position that eventually lands him a career beyond his wildest American dreams.

Best Character Study: The Aviator

In the mid-1900s, Howard Hughes ruled the skies, produced blockbuster films, had a famous secret lover – and struggled with terrible OCD. His obsessive tendencies help him immensely when building his empire, though as any aspiring entrepreneur knows, taking this to the extreme is not at all healthy. Hughes is an exacting boss, artist and pilot, and as he grows older, his condition continues to worsen. Eventually, after a devastating engine malfunction and severe injury, Hughes chooses his passion over all common sense, continuing development on his pet project rather than maintaining his lucrative government contracts. Tragically, Hughes’ OCD leads him to make increasingly rash decisions, including some that draw scrutiny from the FBI. Thankfully though, the film has a silver lining – as you’ll see when you watch it.

Best Crime Drama: The Godfather

The Godfather might seem like an odd choice for this list, but we'd argue that the rise of the Mafia is one of the most fascinating, if gruesome, entrepreneurial stories of all time. Michael Corleone and his father The Godfather (il Padrino in Italian) Vito grow a “family business” into the most menacing powerhouse (albeit an illegal one) in all of New York. This movie shows what can happen when power and money corrupt the entrepreneurial spirit to the extreme, and as such, it’s a must-watch. Just don’t take the Hollywood-level extreme measures as practical business tactics.

Best Drama: Twelve Angry Men

If you’re going to be a top-notch entrepreneur, you’re going to need to learn how to get along with other people. This film is a great example of how to, and how not to, convince other people to see your point of view – especially in the confines of a tiny room. Just 3 of the 96 minutes of this film take place outside of the jury deliberation room, but that doesn’t stop this movie from being an absolute whirlwind. In it, morals are questioned, biases are tested, consensuses are built and destroyed and rebuilt again. You’ll see how personalities can diffuse or intensify an already heated argument, how values inform our decisions – and you’ll likely take a look inside yourself as well.

Best Comedy: Office Space

If you’re looking for inspiration to quit your dreary job and finally start being an entrepreneur, this is the film for you. This absurd movie just might inspire even the timidest deskbound 9-5 person to take the steps they need to escape the office grind. When you don’t work for yourself, nothing you ever do will guarantee you get ahead, as viewers of this film soon learn. As the main character says, “We don't have a lot of time on this Earth! We weren't meant to spend it this way. Human beings were not meant to sit in little cubicles staring at computer screens all day, filling out useless forms and listening to eight different bosses drone on about ​mission statements."

Best Modern Blockbuster: The Social Network

Facebook controls the way we all consume media, whether we like it or not, and this film shows you how it got to be that way. It follows the humble origins of Facebook and crazy culture of Harvard University, along with the interpersonal drama that can come when founders don’t square things away properly before they become successful. The lesson for entrepreneurs here? Make sure you know who is a part of your team, how much they’ll contribute and how much ownership they’ll have in the final product. And when all else fails, get a good lawyer.