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The 20 Best Entrepreneur Movies All Business Owners Must Watch

Rieva Lesonsky

Rieva Lesonsky

Contributor at Fundera
Rieva Lesonsky is a small business contributor for Fundera and CEO of GrowBiz Media, a media company. She has spent 30+ years covering, consulting and speaking to small businesses owners and entrepreneurs.
Rieva Lesonsky
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Of all the TV shows and movies created in entertainment, the best entrepreneur movies tend to hit home the hardest for small business owners. There’s nothing like envisioning yourself on the big screen, especially when the main character is bucking against the establishment, duking it out with the head honcho, and ultimately leaving their 9-5 only to build a legendary business. 

Like the main characters in these films discover, running your own business is hard work. sometimes you just need a little inspiration to get through the rough patches.

Here are 20 of the best movies of all time entrepreneurs and business owners need to watch as soon as possible—and why they relate to small business owners everywhere.

The 20 Best Entrepreneur Movies of All Time

1. “The Social Network” (2010)

The best entrepreneur movies always include some kind of rail against the establishment—and “The Social Network” is no different. This movie details the treacherous path of Facebook’s beginnings when entrepreneurial-minded Mark Zuckerberg (played here by Jesse Eisenberg) launches the social network in his Harvard dorm to get back at a recent ex-girlfriend. Soon enough, with financing from investor and friend Eduardo Saverin, Facebook takes on a life of its own. Ever the believer in his own abilities, Zuckerberg builds Facebook’s platform single-mindedly, ignoring financial requirements, legalities, and other people’s feelings.

When legendary internet entrepreneur and creator of the early-aughts’ Napster Sean Parker comes on board, Saverin is pushed out of the company and Zuckerberg is quickly entangled in a nasty lawsuit over the ownership and rights of Facebook.

Ripe with the drama of building a business that grows to take over the world, and becomes its own universal language, “The Social Network” is a perfect entrepreneur movie (and warning sign) of what can happen when an idea catches the world on fire.

With Facebook’s current relevance in the pop culture zeitgeist, this entrepreneur movie is a must-watch for any business owner who dreams of making it big—and learning the pitfalls of any large endeavor.

Why it’s one of the best entrepreneur movies: The Social Network” captures the archetypes of entrepreneurship and the early rise of the tech world in Silicon Valley, down to the Harvard dorm room, the “coding bros,” and the founder who lacks emotional intelligence.

2. “Jerry Maguire” (1996)

In this entrepreneur tale of the fall and rise of a high-powered sports agent, Jerry Maguire (Tom Cruise) is fired from his successful company after advocating for his belief that agents should have a more personal touch, with fewer clients and more time to understand them. He impulsively starts his own sports management agency with the only client who believes in his newly adopted ethos, Rod Tidwell (Cuba Gooding Jr.), a volatile football player whose family and financial needs push Jerry to become his best.

With former co-worker Dorothy (Renee Zellweger) as his sole employee, Maguire must build his business and overcome both his own doubts and those of his only client. Ultimately, he succeeds by putting his client’s needs before his own desire to make money.

Why it’s one of the best entrepreneur movies: Striking out on your own because you think you can do it better is the classic startup story. It’s scary, sure, but as “Jerry Maguire proves, all you really need is one good customer and a lot of determination.

3. “Joy” (2015)

Another true-to-life entrepreneur movie is “Joy”, the story of entrepreneur and business magnate Joy Mangano. At the start, Mangano (Jennifer Lawrence) lives in a rundown house with two kids, her divorced parents, her grandmother, and her ex-husband (who spends his days doing karaoke in the basement). Her future looks dim until she is struck with that all-encompassing inspiration so familiar to every entrepreneur: an idea for a revolutionary cleaning product called the Miracle Mop.

Although Mangano continuously runs into complications within her family and her home (which is falling apart because she can’t afford repairs), she throws herself into making her business idea a reality. When QVC gives Mangano a chance to promote her mop on air, her passion for the product shines through. This entrepreneur movie results in a truly happy ending as the real-life Joy Mangano is now a multimillionaire with hundreds of patents to her name.

Why it’s one of the best entrepreneur movies: Few movies about small business so accurately capture the craziness that often goes on behind the scenes (like the scramble that Mangano goes through to produce enough units in time for her appearance). Plus, Mangano’s struggle to manage both her family and her business will ring true with almost all entrepreneurs.

4. “Wall Street” (1987)

“Greed is good,“ is the tireless mantra of  “Wall Street”‘s money-obsessed antagonist Gordon Gekko (Michael Douglas). This entrepreneur movie tells the story of Bud Fox (Charlie Sheen), a young and ambitious stockbroker who dives headfirst into the volatile 1980’s stock exchange. With his new boss’s aggressive thesis ingrained into his training, Bud finds himself susceptible to the glamour and excitement of his newfound lifestyle.

Why it’s one of the best entrepreneur movies: A peek into the world of corporate finance, investment, and capital markets, “Wall Street” shows just how slippery the slope of greed truly is, and the ultimate consequences of fraudulent business practices.

5. “The Devil Wears Prada” (2006)

From the real-life story of a young woman determined to make it in publishing comes this tale of the power of success and intimidation. Andy is an aspiring journalist and despite her fashion faux-pas she manages to impress Miranda Priestly (a thinly veiled Anna Wintour), editor-in-chief of the prestigious Runway magazine (a thinly veiled Vogue magazine). What follows is a guide in “How Not To’s” until Andy finds herself rising to the top of her boss’s most trustworthy allies. Eventually, Andy comes to realize that being on top of a heap of The Worst People Ever is not all that it’s cracked up to be, and that she may have lost her inherent sense of ethics and integrity somewhere along her journey to the top.

Why it’s one of the best entrepreneur movies: Andy’s ascent to the top of the fashion A-list ultimately leaves her feeling out of touch and lost despite her success. Similar to “Wall Street”, “The Devil Wears Prada” counters the idea that corporate success and massive wealth indicate a happy life, and instead uncovers the emptiness of such endeavors. Andy moves on from her experience at Runway and is able to follow through and fulfill her original dream of becoming a journalist.

6. “Office Space” (1999)

No one knows the monotony of corporate culture better than Peter Gibbons ( Ron Livingston). Peter’s daily interactions with tedious coworkers and an exhausting boss result in regular daydreams of destroying the software company he works for. Work relationships and office politics are at the center of this satirical comedy, and any entrepreneur who left office existence will relate to the ineffective bureaucracy of corporate life.

Why it’s one of the best entrepreneur movies: Through the lens of a corporate drone, “Office Space” shows how the mindlessness of traditional corporate culture leaves many employees feeling uninspired and passionless. In the end, Peter decides to leave the company and pursue a career that he enjoys—and that’s a story every entrepreneur can relate to.

7. “Erin Brockovich” (2000)

This legal drama brings to light the true story of Erin Brockovich (played by Julia Roberts) and her unlikely win against corporate bigwigs Pacific Gas and Electric Company (PG&E). A previously unemployed mother of three, Brockovich gains favor as a legal researcher in the small town of Hinkley, California, when she learns the residents’ health issues have been brought on from pollution being spread by PG&E. With intense determination and a fearless attitude, Brockovich pursues legal action against the $28 billion corporation and ultimately wins.

Why it’s one of the best entrepreneur movies: Although not an entrepreneur movie in the traditional sense, Brokovich’s real-life story is an inspiration to every entrepreneur inspired by a call to support social responsibility and corporate ethics.

8. “The Founder” (2016)

In this retelling of the founding father of McDonald’s, Ray Kroc is a businessman who cashes in on a restaurant with a new style of food delivery—hamburgers made in 30 seconds, not 30 minutes. Kroc is relentless in his pursuit of building the world’s greatest fast food empire, and his path to greatness doesn’t come without troubles. With endless ideas and determination, Kroc cements the McDonald’s name in history as one of the greatest franchise restaurants of all time.

Why it’s one of the best entrepreneur movies: Building an empire isn’t easy—especially when you’re challenging the status quo. “The Founder” explores the side of business that requires a persistence unknown to many, but will surely inspire entrepreneurs that are determined to create “the next big thing.”

9. “Baby Boom” (1987)

In this female-centric entrepreneur movie, corporate bigwig J.C. Wiatt (Diane Keaton) and her equally workaholic boyfriend (Harold Ramis) find themselves more in love with their careers than each other. When a distant relative dies and appoints J.C. the guardian of a baby girl, her professional life beings to fall apart: her career-obsessed boyfriend leaves her, and juggling her high-powered job and her newly adopted child forces the corporate promotion she was working toward fall down the drain.

When a conniving co-worker stabs her in the back, J.C. makes the decision to quit rather than be fired. She buys a rundown house in Vermont, starts making her own baby food—and before you know it—she’s the founder of a brand new, thriving venture and the hero of her own entrepreneur story.

Why it’s one of the best entrepreneur movies: Baby Boom’s” entrepreneur origin story struck a chord with high-paid corporate executives who left the rat race to start a winery or cheese-making business in the 1990s. For women, the movie captured the beginning of the surge of women-owned businesses and proved that becoming a business owner was better than trying to crash through corporate glass ceilings.

10. “Big Night” (1996)

In “Big Night,” two immigrant Italian brothers—Primo (Tony Shalhoub), a gifted chef, and Secondo (Stanley Tucci), a practical type—start a restaurant. But Primo’s refusal to compromise his “vision,” results in a menu of dishes American customers are unaccustomed to. As a result, the restaurant is nearly forced into an early foreclosure.

Suddenly, another restaurateur promises to convince a popular jazz musician (Louis Prima) to play a fundraiser at the brothers’ restaurant to help get them out of the red. Primo and Secondo work together, throwing their heart and soul into their final “big night,” and it pays off. Even when the promised musician Louis Prima never shows, diners rave about the night’s results and catapults the restaurant into success.

Why it’s one of the best entrepreneur movies: Too many startup entrepreneurs fall prey to Primo’s problem: They try to sell what they think customers want instead of working to discover what customers actually want. “Big Night” illustrates the importance of making compromises to enable people to better work together, and to create a successful business.

11. “Willy Wonka and the Chocolate Factory” (1971)

When eccentric candy-maker Willy Wonka (Gene Wilder) decides he needs to pass his candy empire on to a successor, he selects five lucky children to tour his top-secret chocolate factory, he quickly realizes four of the five children are jaded, bratty, and blasé. But Charlie Bucket, a sweet, impoverished kid, is wide-eyed with delight at the incredible inventions Wonka shares with the group.

The brats meet horrible ends, while a competing candy maker promises Charlie wealth if he’ll smuggle some candy out of the factory. When Charlie refuses, Mr. Wonka tells him he’s “passed the test” and names him as his successor.

Why it’s one of the best entrepreneur movies: Finding a partner who shares your vision is one of the most difficult tasks every entrepreneur faces. This entrepreneur movie proves that though imagination and passion will take you far, you need ethics to create a business that’s worth passing on.

12. “It’s a Wonderful Life” (1946)

A classic and often relatable tale, “It’s a Wonderful Life follows the entrepreneur rise of George Bailey, a young man who grows up in the small town of Bedford Falls with dreams of traveling the world. When his father dies suddenly, however, Bailey reluctantly takes over the family Bailey Bros. Building and Loan to save it from the town miser, Mr. Potter. For years, Bailey sacrifices his dreams of adventure to keep the Building and Loan going—and to help the town’s working people become homeowners instead of renting from slumlord Potter. But when the bank’s entire savings suddenly goes missing, Bailey bitterly wishes he had never been born.

Angel Clarence appears to show Bailey how different Bedford Falls would be if that wish had come true and, as hundreds of friends and neighbors rally around him, Bailey learns just how much his unselfish actions have really mattered.

Why it’s one of the best entrepreneur movies: It’s a Wonderful Life” is a classic tale, and one of the best entrepreneur movies of all time. You could think of George Bailey as the first socially responsible entrepreneur—by putting his town and neighbors first, he succeeded in more than just business—he succeeded in life.

13.Tommy Boy” (1995)

Good-natured but dimwitted Tommy Callahan (Chris Farley) is handed a cushy job at his father’s auto parts factory. But when his father dies of a heart attack, the bank threatens to call in its loan. Callahan’s stepmother and stepbrother want to sell the factory and pay off the loan—but when Callahan finds out that would put all the employees out of work, he vows to save the business himself.

Upon finding out that 500,000 brake pads would result in enough cash to repay the loan, Callahan and his father’s cynical assistant Richard (David Spade) head out on a cross-country road trip to sell the parts. Although Callahan has a lot to learn about business, he has a natural ability to read people—and to close the sale. Callahan and Richard meet their quota and (after quite a few hijinks) head back to Ohio to save the business.

Why it’s one of the best entrepreneur movies: Though it’s a zany farce, “Tommy Boy paints a realistic picture of the close relationships employees and bosses in many small businesses have, and how those friendships can ultimately strengthen the business.

14. “The Intern” (2015)

In the movie “The Intern,” about the Fit founder Jules Ostin (Anne Hathaway) can barely keep her head on straight when her commerce company rockets to success. When the startup hires 70-year-old intern Ben Whittaker (Robert De Niro), Ostin assumes you can’t teach an old dog new tricks. But the wise and observant Whittaker quickly learns from his younger coworkers. He also offers some suggestions to optimize the business, and Ostin grows increasingly reliant on his advice when it proves successful.

When Ostin discovers her husband is cheating on her at the same time investors want to bring on a new CEO, she’s desperate to find more time to spend with her family and save her marriage. Eventually, Ostin agrees to step down. Whittaker points out that she doesn’t need to sacrifice the business she loves for a happy marriage, and that she could maintain both with the other. With Whittaker’s advice, Ostin ultimately decides to stay on as CEO as her husband asks for forgiveness, resulting in a happy ending for both Ostin and Whittaker.

Why it’s one of the best entrepreneur movies: “The Intern” explores age and gender politics, alongside stereotypes about Silicon Valley and romantic comedies in a fresh way. Plus, it’s a rare depiction of a woman entrepreneur who’s as passionate about her business as any man—and a man who supports her decisions and points out that success in one isn’t necessarily a failure in the other.

15. “The Pursuit of Happyness” (2006)

This true story starring Will Smith and his son, Jaden, brings the life of American businessman, Chris Gardner, to the big screen. The movie that centers around Gardner’s struggle with being homeless with his young son.

In the film, he is working as a salesman barely making ends meet when he becomes homeless. Around the same time he meets someone who gives him the chance to intern as a stockbroker eventually leading to a full-time position and a prosperous career.

Why it’s one of the best entrepreneur movies: “The Pursuit of Happyness” is a true story with real lessons that can be learned from it. Although it’s an extreme experience, there are valuable lessons embedded in the movie. Many of those lessons can be gleaned from the talks Gardner has with his son, about never giving up and never letting anyone else define you.

16. “You’ve Got Mail” (1998)

Small business and corporations collide on screen in “You’ve Got Mail.” Meg Ryan and Tom Hanks play two strangers brought together by email and then, unbeknownst to them, by business, as well. Hanks is the heir to a massive book store chain opening around the corner from Ryan’s small independent bookstore. The two strike up an anonymous relationship online before ever meeting in person and connecting the dots.

The two criticize one another in person, and their businesses, with Ryan’s character adamantly against the corporate non-personal Fox Books chain. The romantic comedy may be cheesy but it definitely has a lesson or two hidden about small businesses.

Why it’s one of the best entrepreneur movies: Meg Ryan’s character in the movie, Kathleen Kelly, is passionate about her small business, her bookstore. It’s been a staple in the neighborhood for years, and she’s suddenly faced with a corporate competitor. This is something many small business owners can relate to, and have likely experienced to some degree, or could experience in the future.

17.  “Moneyball” (2011)

You may be wondering what a movie about baseball has to do with business but the lessons in “Moneyball” can actually be applied far outside of the sport. Without the courage to make a change, the entire plot of the movie never would have happened.

Billy Beane, played by Brad Pitt, takes a chance on a new idea and makes big changes to the way he makes his roster for the Oakland Athletics baseball team in the movie. His team loses some of its star players to teams with more money, and he has to figure out a way to create a winning team anyway.

Why it’s one of the best entrepreneur movies: “Moneyball” is about far more than baseball. The important business lessons of being able to adapt, listen to new ideas, and change the way things are usually done, are all core to the success Pitt in the movie, and Beane in real life.

18. Steve Jobs (2015)

Everyone knows Steve Jobs as the iconic turtleneck-wearing founder of Apple. The film “Steve Jobs,” with a screenplay written by Aaron Sorkin and directed by Danny Boyle, delves into the life of the founder of Apple, Inc. The movie offers a look into the mind of Steve Jobs, played by Michael Fassbender, as well as the personal life of the founder.

While the narrative around Jobs focuses on the tremendous success of Apple, the movie shows his failures as well. Putting on display the struggles even the most successful entrepreneurs encounter.

Why it’s one of the best entrepreneur movies: “Steve Jobs” gives you a look into the mind and life of the founder of one of the most popular brands on Earth. The hope for business owners and entrepreneurs is that maybe they can take a page out of his book and create a company a fraction as successful as Apple.

19. “The Big Short” (2015)

“The Big Short” brought actors like Ryan Gosling, Brad Pitt,  and Steven Carrell to the screen together to help give a look into the financial crisis. Three storylines are told simultaneously in the movie to culminate int he realization of an inevitable collapse.

The film takes complex financial events and makes them easier for a non-expert audience to understand, and it brings a hint of humor to lighten the mood a bit. There are a number of cameo appearances from celebrities as well.

Why it’s one of the best entrepreneur movies: “The Big Short” can help shed light on the financial collapse and therefore the financial mindset of many Americans today. It can also give new entrepreneurs an idea of when to push for what they believe in and when to take caution.

20. “Chef” (2014)

This dramedy is about a chef who feels stuck and decides to ditch his restaurant job to start his own business, a taco truck. There’s some truth in it too, food truck owner Roy Choi, co-produced the film.

The movie follows chef Carl Casper, played by Jon Favreau, in his mission to create the food he wants to, with only himself giving direction to his menu. The movie also combines Casper’s personal relationships to show the overlap of work and the personal.

Why it’s one of the best entrepreneur movies: “Chef” shows the benefits of putting it all on the line for your passion. The success and fulfillment don’t come without some struggle but in the end, it’s well worth it all, the movie shows.

Rieva Lesonsky

Rieva Lesonsky

Contributor at Fundera
Rieva Lesonsky is a small business contributor for Fundera and CEO of GrowBiz Media, a media company. She has spent 30+ years covering, consulting and speaking to small businesses owners and entrepreneurs.
Rieva Lesonsky

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