This post includes a collection of the 20 best movies for entrepreneurs. Every entry includes a brief explanation as to why it was chosen and a clickable image-link that will allow you to purchase or rent the movie on Amazon and its respective partners. This list has been sorted in chronological order. I have watched every film listed on here myself and have done my best to not include any spoilers.
I have enabled comments for this post, so if you would like to give some feedback or share your own favourite entrepreneurial film with me, you can do so by typing it into the comments section at the bottom of this page.
May these films inspire you and aid you in whatever goal it is you are wanting to achieve.
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Good Will Hunting (1997)
The film launched the careers of both Ben Affleck and Matt Damon. The story was initially written as an exercise for a playwriting class Matt was taking during his fifth year at Harvard. Ben was asked to help and the play was eventually adapted as a script for the silver screen.
The project was developed by Caste Rock (Rob Reiner’s production company) but they could not figure out what to do with it. The script was eventually taken to Miramax by Kevin Smith where the project finally found a home. Good Will Hunting became Miramax’s highest-grossing film and held the title for 5 years at which point it was topped by Chicago in 2002.
How does this film relate to entrepreneurs? The film speaks to the importance of identifying and overcoming one’s internal conflicts and how when left unresolved, they can become massive stumbling blocks on our journey towards fulfilment and success.
The film received 2 Oscars. Robin Williams won Best Actor in a Supporting Role. Matt Damon and Ben Affleck won Best Writing, Screenplay Written Directly for the Screen.
Pirates of Silicon Valley (1999)
Admittedly this film does not have the best production quality as it was made for television during the late 90s. But it did, however, do a good job of sharing the story of Bill Gates and Steve Jobs and how their respective companies launched the information age and changed the way the world did business for years and decades to come.
One of my favourite parts in the movie was where Bill Gates licenced DOS (Disk Operating System) to IBM without actually owning the rights to the software. He later bought it from a friend for $50 000 which is a drop in the bucket when compared to how much revenue the OS made for Microsoft in the years to follow.
The First $20 Million Is Always the Hardest (2002)
I love this film for how it depicted Silicon Valley and the pitfalls that come with being entrepreneurial and pursuing one’s dreams.
One of my favourite parts is where the protagonist has to ride a bull like a rodeo cowboy for thirty seconds in order to receive the financial backing of a venture capitalist. It serves as a reminder of the importance of stepping outside of our comfort zone in order to achieve one’s goals.
The Aviator (2004)
This might very well be my favourite film of all time. Martin Scorsese pulled out all the stops when directing this film and Leonardo DiCaprio’s performance was impeccable. Robert Richardson, the cinematographer, crafted a visual masterpiece and told the story of this pioneer in a way that very few people in Hollywood could.
Howard Hughes for better or for worse changed the way we use air travel and the impact of his innovation and determination has shaped the modern world and a way that very few people have.
The narrative relates to entrepreneurs because it speaks to the importance of having an unshakable belief in one’s vision. Especially when no one else thinks that the task at hand can be achieved. Hughes repeatedly defies all odds. Sometimes at great cost to his emotional and physical well being.
The film was nominated for eleven Academy Awards and took home five including Best Cinematography, Best Art Design and Best Costume Design.
The Pursuit of Happyness (2006)
Based on a book of the same title The Pursuit of Happyness follows the true story of Chris Garner as he encounters homelessness and the struggles of being a single parent as he takes on an internship at a firm where he wishes to become a stockbroker.
Easily the film’s most emotional scene sees Chris and his son spend the night in a public restroom at a subway station. I love the onscreen chemistry of Will Smith and his son Jaden. I can’t help but think that Will used the project as an opportunity to teach his son about the importance of following one’s dreams in the face of adversity.
The lesson entrepreneurs can take from this film is the importance of listening to one’s intuition and the courage it takes to follow one’s dreams.
Will Smith was nominated for an Academy Award for his portrayal of the film’s protagonist.
The Pixar Story (2007)
The Pixar Story is a very realistic look at what it really takes to become successful. We follow the contributions of Steve Jobs, John Lasseter and Ed Catmull as they come together to combine science, art and business to create something the world has never seen before – an animated feature film made only with computers.
The film explains in great depth the obstacles encountered by the team and how they managed to course correct at times where one wrong decision could mean the end of years of hard work towards manifesting a shared vision.
This film is also a comprehensive study into the world of animation and anybody who enjoys animation will thoroughly enjoy this documentary. I highly recommend it as it is extremely entertaining, very insightful and more informative than one initially expects.
I recommend this film to entrepreneurs because it is an accurate portrayal of the effort sacrifice that comes with achieving something that has never been done before.
This is a story about the importance of resilience and how healthy and honest relationships are pivotal to the success of any entrepreneur.
Sections of the film that really resonated with me include the part where the entrepreneur’s idea is stolen by a large corporation after he shared his ideas and proposals with them.
It is not that I condone this sort of behaviour. But Instead, I applaud the entrepreneur for his ability to put the misfortune behind him and find the strength within to develop something new and better.
Credit is also due to him for practising honesty with his friends and loved ones. It is that very level of integrity that set his investor at ease when his ingenious idea finally revealed itself.
Up in the Air (2009)
Keeping in mind that this film was released in the wake of the 2008 American housing crisis it is easy to see why it was so well received by millions across the world.
My favourite line from the film, which many other budding entrepreneurs would probably also enjoy is: “Anybody who ever built an empire, or changed the world, sat where you are now. And it’s because they sat there that they were able to do it.” – Ryan Bingham
The entrepreneurial lesson in this film speaks to the importance of one’s ability to see the opportunities that present themselves when misfortune hits.
The film was nominated for six Academy Awards including Best Picture, Best Screenplay, Best Directing and numerous Best Performance nominations of its principal cast.
The Social Network (2010)
A thought-provoking look into student culture at one of the world’s most prestigious universities, the film follows the story of Mark Zuckerburg, founder of social media giant Facebook and the journey that lead to his unadulterated success.
The tagline reads: “You don’t get to 100 million friends without making a few enemies.” And after watching this film, one can’t help but believe that the statement is true.
The film’s entrepreneurial appeal lies in the lessons it teaches us about the importance of understanding the human need for significance and how a key component to success lies in falling in love with one’s clients and not one’s products or services.
The film was nominated for eight Academy Awards and won three including Best Screenplay by one of my favourite screenwriters, Aaron Sorkin.
The beauty of this film lies in its protagonist’s ability to question the status quo. By remaining open to the suggestions of new ideas and quantifying his team’s efforts and results, Billy Beane (Brad Pitt’s character) is able to lead major league underdogs, the Oakland A’s, to a never before seen twenty game winning streak. And by doing so, he changes the game of baseball forevermore.
The entrepreneurial takeaway from this film lies in its tag line: “What are you really worth?”
The film was nominated for six academy awards including Best Picture, Best Actor, Best Supporting Actor and Best Adapted Screenplay.
The Wolf of Wall (2013)
Another Martin Scorsese film finds its way to the list and with good reason. The sheer level of excess that transpires in this film is actually appalling. One could argue that the story serves more as a cautionary tale about the dangers of wealth and greed than it does as a biographical depiction of one of Wall Street’s most infamous brokers.
Important lessons for entrepreneurs relate to selling and owning one’s story. Setting aside the controversial acts and deeds depicted in the film, it is very important to appreciate how Jordan took control of his own narrative by writing and releasing his memoirs by way of the book of the same title. He also played a pivotal role in consulting with the creative team by helping them tell his story in a way that stays true to the original content.
Even with his tainted background. Jordan remains a source of great insight into human behaviour and the art of sales.
The film was nominated for five Academy Awards including Best Picture, Best Director and both Best Actor in a Leading and Supporting role. The film grossed $392 million worldwide making it Scorsese’s highest-grossing film to date.
Steve Jobs (2015)
I read the Steve Jobs biography (written by Walter Isaacson) when it was released in October of 2011 and I became an instant fan of the Jobs narrative. Imagine my delight when I heard that Aaron Sorkin, one of my all-time favourite screenwriters, was brought on board to develop the feature film’s script.
The film did an excellent job in highlighting three of the most pivotal days in Jobs’s career. And it depicted him both as the visionary we’ve all come to know and love and as a normal human being who had flaws just like the rest of us.
Entrepreneurial takeaways include the importance of assembling quality teams that consist of people who are masters in their respective fields and the beauty associated with deploying patience when the market has not yet caught up with one’s vision.
All in all, the film did a great job in touching on highlights throughout Steve’s career but I implore everyone to give the biography a thorough read as it contains many more insights into the inner workings of one of our generation’s most influential minds.
The film was nominated for two Academy Awards and won Best Performance by an Actress in a Supporting Role and Best Screenplay at the 2016 Golden Globes.
Walt Before Mickey (2015)
I’ve been a fan of Disney as long as I can remember and some of their characters and animated films have become some of my most cherished cinema and viewing experiences ever.
However, I really had no idea of the trials and tribulations its founder, Walt Disney, had to endure before the company experienced any substantial success. For example, his first animation company went bankrupt and he lost the rights to Oswalt the Lucky Rabbit, his first commercially successful animated star.
The film itself is strangely paced and the actors’ performances are lacking but if you are a fan of Walt and want to learn more about his story, it is a wonderfully informative and a good place to start.
Lessons for entrepreneurs include the importance of owning one’s copyright and harrowing tales about how profit is essential to the success of any business, even if it has established itself as the leader in a particular niche.
The film has no awards to speak of but it is worth mentioning that it is listed as No.4 on Amazon’s list of must-see movies for entrepreneurs.
The Founder (2016)
An extensive look into the origins of the biggest restaurant business in the world. The story follows Ray Crock (Micheal Keaton) as he progresses from milkshake machine salesman to restaurant shareholder, to franchisor of the McDonalds fast-food franchise.
A turning point in Ray’s journey comes when he has a chance encounter with a lawyer who has been admiring the restaurant’s success from a distance. The lawyer helped Ray to understand that the true value of the franchise did not lie in the McDonald’s recipes, though they did play an important part. Instead, the lawyer explained that the majority of the brand’s wealth lay with its physical stores and the lease agreements that came along with them.
Lessons budding entrepreneurs can take from this film is the importance of maintaining quality control throughout the entirety of one’s business experience and how to gain and implement leverage during times of adversity.
Tony Robbins: I Am Not Your Guru (2016)
Anthony Robbins has spent the last four decades helping people create breakthroughs in both their personal lives and their businesses. His client list includes Nelson Mandela, Oprah Winfrey, Andre Agassi, Bill Clinton, Mother Terresa, Micheal Jordan, Diana Princess of Wales and many more.
This documentary visits Tony at Date With Destiny, one of his most sought after and most energetic seminars. And it takes an in-depth look at how participants learn and implement tools and strategies that help them overcome obstacles and achieve results they never thought possible.
Admittedly, this documentary is not for everybody, but Tony’s results do tend to speak for themself. And it’s easy to see why he is considered to be the best performance strategist in the world today.
Honestly, there is so much entrepreneurs can take away from this documentary. Personally, the film has helped me take complete responsibility for my results and actions as well as inspired me to live a life that is fulfilling and adds value to those around me.
The Greatest Showman (2017)
Ever felt out of place or that you didn’t belong? Well, so did the performers of “The Greatest Show on Earth”. And with the guidance, imagination and ambition of their founder, P.T. Barnum, they created an experience so extraordinary that it has since been credited as “the birth of show business”.
The story follows a penniless and orphaned Phineas Taylor Barnum as he journeys into the realm of the strange and bazaar to assemble a series of never before seen oddities and performances and bring it to the high-brow world of 19th century America. The extravaganza was later billed as P.T. Barnum’s Circus and travelled the globe entertaining the curious.
One of my favourite lines from the movies goes: “No one ever made a difference by being like everyone else.” – P.T. Barnum.
The entrepreneurial value of this film lies in the importance of imagination and seeing things as they could be and not as they are. It also plays to the importance of family and how the pursuit of fame can have disastrous repercussions if left unchecked.
The film was nominated for one Academy Award and won Best Original Song at the 2018 Golden Globe Awards.
Bohemian Rhapsody (2018)
This biopic follows the journey of Queen, arguably one of the greatest rock and roll bands of all time. The narrative focuses predominantly on the life of singer and frontman Freddie Mercury and how he defied stereotypes and became one of the most loved entertainers of all time.
The performances are seamless and Rami Malek does an extraordinary job of channelling Mercury’s eccentric behaviour. The soundtrack is superb and I dare say I have yet to come across a motion picture with a better technical approach and implementation than this one.
The tagline is appropriate and reads: “Fearless lives forever.”
Any entrepreneur would do well to implement such an approach when it comes to undertaking their endeavours. The third act also plays on the importance of teamwork and how honest and open communication is pivotal to the success of any group or organisation.
The film was nominated for five Academy Awards and won four including Best Performance, Best Sound Editing and Best Sound Mixing,
General Magic (2018)
General Magic was perhaps the greatest start-up nobody has ever heard of. The documentary follows the tale of what could have been Silicon Valley’s most successful startup and proceeds to tell the cautionary tale of what happens when a great idea is executed at the wrong time.
The most valuable entrepreneurial lesson I learned from this documentary is that failure is only the end if you allow it to be. Getting back up after experiencing disappointment is an integral part of achieving one’s goals. And what we become as a result of the journey towards our dreams is far more important than the end destination.
An extremely powerful quote from the motion picture goes as follows: “Failure isn’t the end. Failure is actually the beginning.” And when looking at where the members of the initial General Magic team eventually ended up. It’s easy to see that the statement rings true.
Ready Player One (2018)
There is so much I loved about this film and it is easy to see why legendary filmmaker Steven Spielberg wanted to add this project to his list of mind-blowingly awesome movies he has directed. The motion picture is based on the novel by the same name and the production companies that commissioned the film were smart enough to bring the original writer on board to help develop the screenplay.
The visual world is beautiful and the homage and references to numerous pop culture properties were more entertaining than I ever could have imagined.
The narrative does have a classic good vs. evil feel about it but what resonated with me the most was the Halliday character and how he questioned the norm and broke free from convention and expectation.
The entrepreneurial take away I got from this film is that taking a different approach is not necessarily a bad thing, especially if the end result brings so much value to the end-user.
The film was nominated for one Academy Award in the field of Visual Effects.
Ford v Ferrari (2019)
It’s amazing what a little bit of competition can accomplish. As indicated by its title, the film follows the professional rivalry between Ford and Ferrari in anticipation of the 1966 24h La Mans tournament.
The film appealed to the achiever in me because it placed a lot of emphasis on the importance of instinct over calculation. There is a lot one can learn from an academic approach but in the end, the best teacher is experience. And it is this fundamental understanding that allowed Ford’s design team to reapproach how they had been developing the Mustang in years past.
The film speaks to the dangers of bureaucracy that is common in the corporate world but also tips its hat to those who place personal and spiritual growth above monetary gain.
There is a scene where Ken Miles (Christian Bale) talks to his son about the importance of feeling the car and not just dropping one’s foot on the gas pedal to try and win the race. And I thought that that was such a beautiful metaphor for life and how we should approach the way we pursue our ambitions and dreams.
The film was nominated for four Academy Awards and won two.
About the blogger.
Julius Jooste holds an international diploma in IT Engineering as well as a bachelor’s degree in Motion Picture from AFDA, one of the world’s most esteemed film schools. His career has seen him work closely with some of the worlds most prestigious broadcasters and he has established himself as the go-to brand consultant for some of dance music’s most established artists, promoters, events and festivals. Should you like to learn more about the services he offers or would like to view some of the work in his portfolio, you may do so by navigating through the menus found at the top of this page.