Top 20 Movies on Entrepreneurship to Watch in 2024

Have you ever dreamt of turning your brilliant idea into a thriving business? Maybe you’re already knee-deep in the startup hustle, facing the exhilarating challenges and exhilarating rewards of being your own boss. Whether you’re seeking a spark of inspiration or a relatable portrayal of the entrepreneurial journey, the world of cinema offers a treasure trove of films to fire you up. So, grab some popcorn, settle in, and get ready to dive into a world of innovation, resilience, and the pursuit of success.

Top 20 Movies About Entrepreneurship

Whether you’re a seasoned business owner or a dreamer with a million-dollar concept, there’s something undeniably inspiring about seeing others turn their visions into reality. So here’s a list of best entrepreneurship movies.

Any Given Sunday

Year: 2005
Director: Oliver Stone
Stars: John Beard, Tim Belden, Barbara Boxer
IMDb Rating: 7.6/10
Trailer: Here

Forget the glossy boardrooms and million-dollar pitches. In “Any Given Sunday,” the battlefield of entrepreneurship is a gridiron painted green. Buckle up for a brutally honest portrayal of the business of professional football, where coaches scramble for relevance, star players fight for their shot, and ownership prioritizes profit over passion.

Enron: The Smartest Guys in the Room

Year: 2005
Director:Alex Gibney
Stars: John Beard, Tim Belden, Barbara Boxer
IMDb Rating: 7.6/10
Trailer: Here

The world of business is often glamorized, painted as a playground for innovative minds and high-stakes deals. But behind the polished facades and soaring stock prices, darkness can lurk. “Enron: The Smartest Guys in the Room” is full of greed, corruption, and the devastating consequences of unchecked ambition. This documentary explores the meteoric rise and spectacular collapse of Enron, once an energy giant brought to its knees by a web of lies and financial trickery.

Glengarry Glen Ross

Year: 1992
Director: James Foley
Stars: Al Pacino, Jack Lemmon, Alec Baldwin
IMDb Rating: 7.7/10
Trailer: Here

Buckle up for the harsh reality of cutthroat salesmanship in David Mamet’s scathing masterpiece, “Glengarry Glen Ross.” Here, the American Dream is a mirage shimmering in the Florida heat, relentlessly pursued by a band of desperate real estate salesmen. This ain’t your typical entrepreneur movie. “Glengarry Glen Ross” throws us into a pressure cooker of ruthless competition, questionable ethics, and the gnawing fear of failure.

Middle Men

Year: 2009
Director: George Gallo
Stars: Luke Wilson, Giovanni Ribisi, Gabriel Macht
IMDb Rating: 6.8/10
Trailer: Here

This film isn’t your typical Silicon Valley startup tale. Forget sleek offices and venture capitalists. Here, we discover the grittier side of the web’s Wild West days, where a chance encounter between a disillusioned businessman and two tech-savvy hustlers leads them down a path paved with online adult entertainment and high-stakes billing schemes. Buckle up for a fast-paced ride filled with questionable morals, big money, and the unexpected consequences of chasing entrepreneurial success.

MoneyBall

Year: 2011
Director: Bennett Miller
Stars: Brad Pitt, Robin Wright, Jonah Hill
IMDb Rating: 7.6/10
Trailer: Here

The world of baseball is a multi-million dollar spectacle. Teams with bulging wallets scoop up the biggest names, seemingly buying their way to victory. But what happens when you’re the underdog, a small-market team with a shoestring budget? Enter Billy Beane, the maverick General Manager of the Oakland A’s, in Moneyball. Facing an uphill battle against the financial giants, Billy throws out the traditional rulebook. He embarks on a revolutionary approach, assembling a winning team not with superstars, but with overlooked players and a whole lot of statistics.

Office Space

Year: 1999
Director: Mike Judge
Stars: Ron Livingston, Jennifer Aniston, David Herman
IMDb Rating: 7.6/10
Trailer: Here

Have you ever stared at your computer screen, willing the day to fast forward to quitting time? Does the mere mention of “flair” send shivers down your spine? If so, then welcome to Initech, the soul-crushing office environment that Peter Gibbons and his fellow cubicle dwellers call home (or at least purgatory) in the cult classic “Office Space.” This satirical comedy isn’t a cliche entrepreneurship story. Instead, it takes a hilarious and relatable look at the corporate world’s absurdities, the soul-sucking routines, and the yearning for freedom that can simmer beneath the surface of even the most seemingly docile employee.

Silicon Cowboys

Year: 2016
Director: Jason Cohen
Stars: Rod Canion, Jim Harris, Bill Murto
IMDb Rating: 6.9/10
Trailer: Here

Buckle up for a David vs. Goliath tale set in the heart of Texas! “Silicon Cowboys” chronicles the underdog story of Compaq, a scrappy startup founded by three friends in a Houston diner. Their audacious dream? To build a portable computer and challenge the reigning tech giant, IBM, for PC supremacy. In 1981, the idea seemed crazy. But these cowboys weren’t afraid to take on the establishment. Get ready for a wild ride filled with innovation, fierce competition, and the birth of a revolution that would change the way we work and live.

Silicon Valley

Year: 2014
Director: Alex Garland
Stars: Alicia Vikander, Domhnall Gleeson, Oscar Isaac
IMDb Rating: 7.7/10
Trailer: Here

Forget dusty trails and six-shooters. In the untamed frontier of Silicon Valley, the new breed of cowboys wrangles circuits and wields code. Buckle up for “Silicon Cowboys,” the true story of three Texas pals who dared to challenge the tech goliath, IBM. In a David vs. Goliath showdown for the ages, this film chronicles their wild ride from a late-night diner napkin sketch to building the world’s first portable computer and taking on the industry giant. Prepare to be inspired by their audacious dream, fueled by Texas grit and a whole lot of innovation.

Steve Jobs: The Lost Interview

Year: 2012
Director: Paul Sen
Stars: Robert X. Cringely, Steve Jobs
IMDb Rating: 8.0/10
Trailer: Here

Steve Jobs, the name synonymous with innovation, design, and a touch of rebellion, revolutionized the way we interact with technology. But beyond the iconic Apple products, there lies a story of passion, purpose, and the relentless pursuit of a vision. “Steve Jobs: The Lost Interview” offers a rare glimpse into the mind of this enigmatic leader.

Thank You for Smoking

Year: 2005
Director: Jason Reitman
Stars: Aaron Eckhart, Cameron Bright, Maria Bello
IMDb Rating: 7.5/10
Trailer: Here

Forget Steve Jobs and Mark Zuckerberg. In the world of “Thank You for Smoking,” the hottest entrepreneur isn’t building a tech empire, he’s spinning one. Meet Nick Naylor, the smooth-talking, sharp-witted VP of the Academy of Tobacco Studies. Nick’s a master manipulator, a champion of cigarettes in a world increasingly focused on health. This isn’t your typical rags-to-riches story. It’s a hilarious satire that explores the dark underbelly of corporate influence and the lengths people go to in the name of profit.

The Aviator

Year: 1987
Director: Martin Scorsese
Stars:Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale
IMDb Rating: 7.5/10
Trailer: Here

Fasten your seatbelts, because we’re taking a flight into the captivating world of Howard Hughes in Martin Scorsese’s epic biopic, “The Aviator.” This isn’t your typical rags-to-riches story. Howard Hughes was a whirlwind – a visionary film producer, a record-breaking aviator, and a relentless innovator. But his ambition was matched only by his demons. “The Aviator” isn’t just a chronicle of success; it’s a portrayal of the soaring highs and the crippling lows that come with chasing a dream at breakneck speed. Prepare to be enthralled by Leonardo DiCaprio’s electrifying performance as Hughes, and to witness a man who dared to push the boundaries of possibility, both in the skies and in Hollywood.

The Big Short

Year: 2015
Director: Adam McKay
Stars:Christian Bale, Steve Carell, Ryan Gosling
IMDb Rating: 7.8/10
Trailer: Here

This film takes you deep into the unorthodox world of a few financial outsiders who saw the housing market teetering on the brink of collapse – and saw an opportunity. Based on Michael Lewis’s gripping book, “The Big Short” isn’t a standard Wall Street drama. It’s a darkly funny, thought-provoking exploration of the ingenuity (and audacity) of a handful of investors who dared to bet against the entire system.

The Dropout

Year: 2022
Director: Elizabeth Meriwether
Stars: Amanda Seyfried, Naveen Andrews, Michel Gill
IMDb Rating: 7.5/10
Trailer: Here

Silicon Valley: a land of audacious ideas, boundless ambition, and sometimes, spectacular flameouts. “The Dropout” takes us inside the story of Elizabeth Holmes, a young entrepreneur who captivated the world with a revolutionary healthcare technology. Holmes, a charismatic Stanford dropout, promised to revolutionize blood testing with a single drop. But beneath the sleek facade and promises of changing the world, a different story unfolds.

The Donut King

Year: 2020
Director: Alice Gu
Stars:Ted Ngoy, Christie Suganthini, Chet Ngoy
IMDb Rating: 7.1/10
Trailer: Here

This documentary follows Ted Ngoy, a Cambodian refugee who rose from humble beginnings to become a donut mogul, building a multi-million dollar empire from the ground up. The Donut King is more than just a love letter to America’s favorite pastry; it’s a tale of grit, determination, and the unexpected paths to achieving one’s goals. So, ditch the suits and ties, and get ready for a heartwarming journey.

The Founder

Year: 2016
Director: John Lee Hancock
Stars: Michael Keaton, Nick Offerman, John Carroll Lynch
IMDb Rating: 7,2/10
Trailer: Here

Forget everything you thought you knew about the golden arches. “The Founder” isn’t a feel-good story about the birth of a fast-food empire. It’s a gripping tale of ambition, betrayal, and the ruthlessness that can lurk beneath the surface of the American dream. We meet Ray Kroc, a struggling salesman peddling milkshake machines, who stumbles upon a revolutionary burger joint run by the McDonald brothers. Blinded by potential, Kroc recognizes an opportunity that will change his life, but not necessarily for the better.

The Pursuit of Happyness

Year: 2006
Director: Gabriele Muccino
Stars: Will Smith, Thandiwe Newton, Jaden Smith
IMDb Rating: 8.0/10
Trailer: Here

Homelessness. Single fatherhood. A relentless pursuit of a better life. These are the ingredients that make up “The Pursuit of Happyness,” a film that transcends the typical entrepreneur narrative. It’s not just about building a business empire; it’s about the unwavering spirit that propels a man named Chris Gardner towards a future he desperately craves for himself and his son.

The Social Network

Year: 2010
Director: David Fincher
Stars: Jesse Eisenberg, Andrew Garfield, Justin Timberlake
IMDb Rating: 7.8/10
Trailer: Here

This movie is a human drama exploring the price of fame, the value of friendship, and the murky line between competition and cutthroat tactics. With a sharp script and a captivating performance by Jesse Eisenberg as Zuckerberg, “The Social Network” offers a thought-provoking look at the dark side of ambition and the power a single idea can have on the world.

The Startup Kids

Year: 2012
Director: Vala Halldorsdottir, Sesselja Vilhjalmsdottir
Stars: Trip Adler, Alexa Andrzejewski, Mike Butcher
IMDb Rating: 6.6/10
Trailer: Here

“The Startup Kids” shines a light on a different breed of entrepreneur: the tech-savvy youth who are changing the game from their bedrooms and garages. This 2012 documentary explores the world of young web pioneers, following their journeys as they build the next big thing in the digital realm. Get ready to meet the future of tech! “The Startup Kids” offers a glimpse into the minds of the founders behind companies like Vimeo, Dropbox, and Soundcloud.

Wall Street

Year: 1987
Director: Oliver Stone
Stars: Charlie Sheen, Michael Douglas, Tamara Tunie
IMDb Rating: 7.3/10
Trailer: Here

In the heart of New York City, where ambition roars louder than the sirens, lies a world of high-stakes deals and ruthless ambition: Wall Street. Oliver Stone’s 1987 classic, “Wall Street,” plunges us into this exhilarating yet treacherous landscape, following Bud Fox, a young stockbroker hungry for success. Fox becomes enmeshed in the orbit of Gordon Gekko, a titan of the financial world, whose mantra of “greed is good” embodies the cutthroat reality of chasing wealth on Wall Street. “Wall Street” isn’t just a thrilling drama; it’s a cautionary tale for those who yearn to play the game at any cost.

The Great Hack

Year: 2005
Director: Karim Amer, Jehane Noujaim
Stars: Brittany Kaiser, David Carroll, Paul-Olivier Dehaye
IMDb Rating: 7.0/10
Trailer: Here

“The Great Hack” takes us into the darker side of the startup world, where ambition meets exploitation. This isn’t a feel-good tale of building the next billion-dollar app. This documentary exposes the Cambridge Analytica scandal, where a data firm allegedly harvested millions of Facebook profiles to manipulate voters in pivotal elections. “The Great Hack” isn’t just about entrepreneurship; it’s a cautionary tale about the ethical tightrope walk faced by those wielding immense power over our digital lives.

In conclusion, the journey of entrepreneurship is a thrilling blend of creativity, risk, and perseverance. These top 20 movies about entrepreneurship not only entertain but also provide invaluable insights and motivation for anyone looking to embark on or continue their own business adventure. Each film showcases unique aspects of the entrepreneurial spirit, from the initial spark of an idea to the relentless drive needed to overcome obstacles. So, whether you’re at the beginning of your startup journey or well on your way, let these cinematic stories fuel your passion and remind you that with determination and innovation, success is within reach.