The 9 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

Running your own business is hard work, and sometimes you need a little entertainment. Why not get some inspiration, too?

Here are nine of the best entrepreneur movies of all time—and why.

The 9 Best Entrepreneur Movies of All Time

1. Willy Wonka and the Chocolate Factory (1971)

When eccentric chocolate-maker Willy Wonka (Gene Wilder) selects five lucky children to tour his top-secret factory, four of them 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, Wonka tells him he’s “passed the test” and names him as his successor.

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

2. Baby Boom (1987)

Corporate bigwig J.C. Wiatt (Diane Keaton) and her equally workaholic boyfriend (Harold Ramis) are more in love with their jobs than each other. Then a distant relative dies and leaves J.C. a baby girl. While trying to figure out who can take the baby, J.C. unexpectedly falls in love with the child. Her boyfriend leaves her, and the corporate promotion she was working toward makes it more difficult to juggle her career and her new baby.

When a conniving coworker stabs her in the back, J.C. quits 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 thriving business. (She also lands a cute new boyfriend.)

Why it’s one of the best entrepreneur movies: Baby Boom 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, it captured the beginning of the surge of women-owned businesses and showed that being a business owner was better than trying to crash through corporate glass ceilings.

3. The Social Network (2010)

When considering the best entrepreneur movie—The Social Network is a must. Mark Zuckerberg (Jesse Eisenberg) launches a social network app in his Harvard dorm to get back at an ex-girlfriend. But with financing from his friend Eduardo Luiz Saverin, Facebook soon takes on a life of its own. The socially awkward Zuckerberg pursues his idea single-mindedly, ignoring legalities like contracts and niceties like other people’s feelings.

When legendary internet entrepreneur Sean Parker comes on board, Saverin is pushed out of the company and Zuckerberg ultimately gets entangled in a nasty lawsuit over who really started Facebook.

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

4. It’s a Wonderful Life (1946)

George Bailey grows up in the small town of Bedford Falls with dreams of traveling the world. When his father dies unexpectedly, however, Bailey reluctantly takes over the family Bailey Bros. Building and Loan to save it from the town miser, Mr. Potter. This is a classic and perhaps one of the best entrepreneur movies of all time.

For years, George sacrifices his dreams to keep the Building and Loan going—and help the city’s working people become homeowners instead of renting from slumlord Potter. But when the bank’s entire savings suddenly goes missing, George bitterly wishes he had never been born.

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

Why it’s one of the best entrepreneur movies: You could think of George Bailey as the first socially responsible entrepreneur. By putting other people first, he succeeded at more than just business—he succeeded at life.

5. Joy (2015)

Joy 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 prospects look dim until she comes up with the idea for a revolutionary product, the Miracle Mop.

With her grandmother supporting her, the rest of her family getting in the way, and her house falling apart because she can’t afford repairs, Joy throws herself into making her project a reality. When QVC gives Joy a chance to promote her mop on the air, her passion for the product shines through. Happy ending: 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 Joy goes through to produce enough units in time for her appearance). Plus, Joy’s struggle to manage both her family and her business ring true with many female entrepreneurs.

6. Big Night (1996)

Two immigrant Italian brothers—Primo (Tony Shalhoub), a gifted chef, and Secondo (Stanley Tucci), a practical type—start a restaurant. But Primo refuses to compromise his “vision,” so he’s creating dishes American customers have never heard of. As a result, the restaurant is about to go into foreclosure.

Then another restaurateur says he can get a popular jazz musician (Louis Prima) to play a fundraiser at the brothers’ restaurant and get them out of the red. The brothers work together, throwing their heart and soul into their “big night,” and the diners rave about the results—even though Louis Prima never shows.

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 what customers actually want. Big Night illustrates the importance how making compromises enables people to better work together, to create a successful business.

7. Jerry Maguire (1996)

High-powered sports agent Jerry Maguire (Tom Cruise) gets fired after venting his belief that agents should have fewer clients and spend more time with each of them. He impulsively decides to start his own sports management agency but can only convince one client (Cuba Gooding Jr.), a volatile football player, to go with him.

With former co-worker Dorothy (Renee Zellweger) as his sole employee, Maguire must struggle to 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 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 than the company you work for is the classic startup story. It’s scary, sure, but as this movie shows, all you really need is one good customer and a lot of determination.

8. 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. Tommy’s stepmother and stepbrother want to sell the factory and pay off the loan. But when Tommy finds out that would put all the employees out of work, he vows to save the business himself.

Selling 500,000 brake pads would be enough to repay the loan, so Tommy and his father’s cynical assistant Richard (David Spade) head out on a cross-country road trip. While Tommy has a lot to learn about business, he has a natural ability to read people—and to make the sale. Tommy 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: It’s a zany farce, but Tommy Boy paints a realistic picture of the close relationships employees and bosses in many small businesses have, and how those friendships can strengthen the business.

9. The Intern (2015)

About the Fit, the commerce business Jules Ostin (Anne Hathaway) started, is growing so fast she can barely keep her head on straight. When the company hires a 70-year-old intern, Ben Whittaker (Robert De Niro), Hathaway assumes he’s useless. But the wise and observant Ben quickly learns from his young coworkers. He also offers some suggestions about running a business, and Jules grows to rely on his advice.

She discovers her husband is cheating on her—at the same time investors want to bring on a new CEO. Desperate to find more time to spend with her family and save her marriage, Jules agrees to step down. Then Ben points out that she shouldn’t sacrifice the business she loves, and should be able to have both a happy marriage and a successful company. She stays on as CEO, her husband asks for forgiveness, and all ends well.

Why it’s one of the best entrepreneur movies: The Intern explores stereotypes about age, sex, Silicon Valley, and romantic comedies in a fresh way. Plus, it’s the rare depiction of a woman entrepreneur who’s as passionate about her business as any man—and a man who supports that.

Editorial Note: Any opinions, analyses, reviews or recommendations expressed in this article are those of the author’s alone, and have not been reviewed, approved, or otherwise endorsed by any of these entities.
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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