Top Entrepreneurship Movies and TV Shows to Watch in 2025
Top Entrepreneurship Movies and TV Shows to Watch in 2025
May 12, 2024, 26 min read
Table of Contents
Have you ever dreamt of turning your brilliant idea into a thriving business? I don’t know how to say this, but, so did a lot of people. Maybe you’re already knee-deep in the startup hustle, facing the exhilarating challenges and rewards of being your boss. Perhaps you’re seeking a spark of inspiration or a relatable portrayal of the entrepreneurial journey. Either way, 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 with these top entrepreneurship movies.
Top 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.
A Beautiful Mind
Year: 2001 Director: Ron Howard Stars: Russell Crowe, Ed Harris, Jennifer Connelly IMDb Rating: 8.2/10
You know, there’s something oddly comforting about watching someone smarter than you spiral into chaos. Don’t worry though babes, he still comes out the other side with the brilliance intact. A Beautiful Mind isn’t just about math or mental illness, it’s much more twisted than that. It’s about obsession, isolation, and the quiet war between your demons and your drive. John Nash doesn’t build a startup, but he does build something rarer. He builds a legacy born from sheer intellectual resilience. For any entrepreneur who’s ever felt like they’re too weird, too intense, or too alone in their ideas, this one hits deep. If you haven’t already, watch it! If you did, rewatch it!
Boiler Room
Year: 2000 Director: Ben Younger Stars: Giovanni Ribisi, Vin Diesel, Nia Long IMDb Rating: 7.0/10
If The Wolf of Wall Street is cocaine and yachts, Boiler Room is Red Bull and moral decay. Giovanni Ribisi plays a college dropout chasing fast money in a sketchy stock brokerage that runs on ego, manipulation, and way too many motivational speeches. Also, yes—that’s Vin Diesel, back when he still had hair (jk). This movie isn’t a startup fairytale, but it is a cautionary tale about what happens when ambition outpaces ethics. For any entrepreneur, it’s a reminder: just because it’s legal, doesn’t mean it’s right. Also hype can only carry you so far before someone checks the books. Ready for a night of moral dilemmas?
Catch Me If You Can
Year: 2002 Director: Steven Spielberg Stars: Leonardo DiCaprio, Tom Hanks, Christopher Walken IMDb Rating: 8.1/10
Our pretty boy Leo, bending the law? YES. Before he was out here fighting bears (bows head) and dating women who weren’t born yet when this movie came out, Leonardo DiCaprio played one of the slickest scammers in history. The thing is he somehow made it look charming. Catch Me If You Can is technically about fraud, sure, but at its core, it’s about thinking fast, adapting faster, and selling a story so well people don’t question the plot. Frank Abagnale might’ve been on the wrong side of the law, but the entrepreneurial mindset? Unmatched. Improvisation, hustle, insane confidence—it’s a masterclass in persuasion, minus the ethics (so maybe don’t take all the notes).
Chef
Year: 2014 Director: Jon Favreau Stars: Jon Favreau, Robert Downey Jr., Scarlett Johansson IMDb Rating: 7.3/10
Before he was directing billion-dollar Marvel blockbusters, Jon Favreau was out here making grilled cheese like his life depended on it. If you ask me, honestly, that grilled cheese deserves an Oscar. Chef is a warm, messy, deeply satisfying look at what it means to start over and build something with heart. It’s about passion, creativity, and flipping the bird to the corporate. For entrepreneurs, especially creatives, this movie is therapy. It’s about betting on yourself, failing loudly, and feeding your soul (and maybe your customers) one perfectly crispy Cubano at a time.
The Devil Wears Prada
Year: 2006 Director: David Frankel Stars: Meryl Streep, Anne Hathaway, Emily Blunt IMDb Rating: 6.9/10
Meryl Streep. Anne Hathaway. Emily Blunt. Stanley Tucci. Stanley freaking Tucci. Do I need to say more? It’s literally everyone good in one film. The Devil Wears Prada might be dressed like a fashion movie, but under the Chanel and snark is a brutal lesson in hustle, sacrifice, and knowing your worth. It’s about the cost of climbing the ladder in a high-pressure industry and figuring out whether the view at the top is even worth it. Entrepreneurs will relate to the grind, the burnout, and the quiet power of walking away when something no longer aligns with your values. Get your head out the gutter and watch the masterpiece, please.
Air
Year: 2023 Director: Ben Affleck Stars: Matt Damon, Ben Affleck, Viola Davis IMDb Rating: 7.5 /10
It’s not about the shoe—it’s about believing it will fit. Air tells the story of how Nike bet everything on a young Michael Jordan, and how that single leap of faith reshaped sports, branding, and business forever. Matt Damon’s scrappy marketing exec, Viola Davis is channeling ultimate mom-ager energy. Ben Affleck is directing with just the right mix of nostalgia and bravado, so it all hits. For entrepreneurs, this isn’t just a movie—it’s a blueprint: take the risk, build the story, and never settle for safe.
BlackBerry
Year: 2023 Director: Matt Johnson Stars: Jay Baruchel, Glenn Howerton, Cary Elwes IMDb Rating: 7.3 /10
Another in-your-face title that shows how success is made. The meteoric rise and dramatic fall of BlackBerry, the world’s first smartphone, takes center stage in this gripping drama. The film explores the groundbreaking innovation, internal conflicts, and external pressures that propelled the company to global success—and ultimately led to its collapse in the face of fierce competition.
Print the Legend
Year: 2014 Directors: Luis Lopez, Clay Tweel Starring: Bre Pettis, Max Lobovsky, Cody Wilson IMDb Rating: 7.0/10
This documentary dives into the 3D printing boom, where idealism, innovation, and ego collide in a race to control the future of hardware. It’s part tech gold rush, part moral crisis, and part startup culture microscope. The people building the future here aren’t trying to be liked they’re trying to win. And watching their values bend in real time is as fascinating as the tech itself.
You’ve Got Mail
Year: 1998 Director: Nora Ephron Stars: Tom Hanks, Meg Ryan, Greg Kinnear IMDb Rating: 6.7/10
Yes, it’s a rom-com. But it’s also a surprisingly sharp take on market consolidation, big-vs-small business, and what it feels like to watch your life’s work get steamrolled by a larger, sleeker machine. Tom Hanks runs the Barnes & Noble-type goliath; Meg Ryan owns the indie bookstore with heart. Entrepreneurs will recognize both the thrill of scaling—and the heartbreak of being outscaled.
Walt Before Mickey
Year: 2015 Director: Khoa Le Stars: Thomas Ian Nicholas, Jon Heder, Jodie Sweetin IMDb Rating: 5.8/10
Before the empire, there was just a broke guy with a sketchbook, rejection letters, and one idea that finally landed. Walt Before Mickey isn’t perfect, but it’s honest about what early-stage creative failure actually looks like. It’s something like constant pivots, bankruptcy, legal issues, and that one last gamble that might make it all work. Founders with a rough start will feel seen.
The Godfather
Year: 1972 Director: Francis Ford Coppola Stars: Marlon Brando, Al Pacino, James Caan IMDb Rating: 9.2/10
No, you’re not starting a mafia. But The Godfather is still one of the greatest business films ever made. It’s about power, strategy, loyalty, and how leadership gets handed down whether you’re ready or not. Every move in this film is a lesson in negotiation, leverage, and long-term vision. Entrepreneurs obsessed with scaling without sacrificing control—this is your case study.
Basically Hollywood letting Hugh Jackman be his theatre-kid-self for the whole movie. All spectacle, no shame. The Greatest Showman turns the origin story of P.T. Barnum into a musical about branding, storytelling, and giving people something they didn’t know they needed—then selling it back to them with fireworks. Accuracy? Questionable. Showmanship? Untouchable. For entrepreneurs, it’s a reminder that hype is a business model. Just make sure the product holds up once the curtain drops.
Ferrari
Year: 2023 Director: Michael Mann Stars: Adam Driver, Penélope Cruz, Shailene Woodley IMDb Rating: 6.8 /10
Adam Driver has played a lot of intense men, but as Enzo Ferrari, he takes “brooding visionary” to a whole new gear. Ferrari isn’t only about the glamour of fast cars. It’s about obsession, grief, and the pressure to keep a dream alive when everything’s falling apart behind the scenes. It’s quiet, moody, and driven (pun intended) by the tension of building something iconic while your personal life explodes. Entrepreneurs will feel this in their bones, promise.
Lo and behold for our first TV Show of the list. This Swedish miniseries tells the story of how Spotify was built—one stubborn coder, one risky bet, and a whole music industry ready to sue. Each episode is told from a different perspective—founder, coder, artist, investor—which makes it way more layered than your average startup biopic. It’s intense, a little messy, and totally real about how innovation isn’t just about solving problems—it’s about surviving the politics, egos, and legal nightmares that come with success.
Self Made
Year: 2020 Directors: Kasi Lemmons, DeMane Davis Stars: Octavia Spencer, Tiffany Haddish, Carmen Ejogo IMDb Rating: 7.3/10
Now the next one is a diva on its own. Self Made follows Madam C.J. Walker, the first self-made female millionaire in America, played with unstoppable energy by Octavia Spencer. It’s a fast-paced, emotionally rich series that digs into what it really means to scale a business when the world is stacked against you. Racism, sexism, even sabotage from other entrepreneurs are in play here. For anyone building something from scratch, this series is pure fuel. It reminds you that success isn’t about what you start with, it’s about how relentless you’re willing to be.
The Wolf of Wall Street
Year: 2013 Director: Martin Scorsese Stars: Leonardo DiCaprio, Jonah Hill, Margot Robbie IMDb Rating: 8.2/10
The Wolf of Wall Street doesn’t really require an introduction. Like it really doesn’t. Just close your eyes, mentally get ready, and watch it!
Joy
Year: 2015 Director: David O. Russell Stars: Jennifer Lawrence, Robert De Niro, Bradley Cooper IMDb Rating: 6.6/10
Joy is one of the movies Jennifer and Bradley did while they were the hot couple. The movie starts with a divorced mom inventing a better mop while her entire family doubts her existence. Jennifer Lawrence plays Joy Mangano, the real-life legend who turned a simple household product into a multimillion-dollar empire through QVC grit and pure delusion-fueled perseverance. Bad business partners? Check. Financial chaos? Yep. Passive-aggressive relatives who don’t believe in you until you’re on TV? Absolutely. For entrepreneurs, Joy is the story of what it means to keep building especially when no one claps. And yes, you will want to clean your whole house afterward. Efficiently.
Pirates of Silicon Valley
Year: 1999 Director: Martyn Burke Stars: Noah Wyle, Anthony Michael Hall, Joey Slotnick IMDb Rating: 7.2/10
Before the streaming biopics, before the Apple keynotes, there was Pirates of Silicon Valley. This movie is a raw, weirdly theatrical HBO film that takes you deep into the early days of Apple and Microsoft. Think garage hacking, ego battles, and two dudes trying to reinvent the future while looking like they haven’t slept in three days. Noah Wyle plays Steve Jobs with unsettling intensity, and Anthony Michael Hall turns Bill Gates into a calculating disruptor with a terrifying smile. It’s a little dated, but that kind of adds to the charm. For entrepreneurs, it’s a reminder that even the legends started with stolen code, awkward pitch meetings, and a whole lot of chaos.
Slumdog Millionaire
Year: 2008 Director: Danny Boyle Stars: Dev Patel, Freida Pinto, Saurabh Shukla IMDb Rating: 8.0/10
Jamal isn’t an entrepreneur, but his story might resonate more than most founder films. He doesn’t pitch a product. He survives, adapts, and figures things out one situation at a time. Slumdog Millionaire is about learning by doing, and how experience becomes knowledge in unexpected ways. It’s fast, brutal in places, and honest about how success often looks accidental from the outside—but rarely is. Entrepreneurs will recognize the same pattern: not knowing everything, but knowing enough to keep going.
Startup.com
Year: 2001 Director: Chris Hegedus, Jehane Noujaim Stars: Kaleil Isaza Tuzman, Tom Herman IMDb Rating: 7.1/10
This documentary follows the rise and fall of a real-life internet startup, providing an inside look at the dot-com boom and bust. It’s a raw and revealing portrait of the challenges of entrepreneurship.
Tetris
Year: 2023 Director: Jon S. Baird Stars: Taron Egerton, Nikita Efremov, Sofia Lebedeva IMDb Rating: 7.4/10
Tetris isn’t just a game. It was a Cold War tech heist hiding in a licensing deal. This film tracks how one man tried to secure global rights to the most addictive block game in history, navigating Soviet bureaucracy, Nintendo politics, and enough legal chaos to make your startup’s first term sheet look like a coloring book. It’s fast, clever, and packed with risk. For founders, it’s a reminder that sometimes the product isn’t enough—you’ve got to win the game behind the game.
Dangal
Year: 2016 Director: Nitesh Tiwari Stars: Aamir Khan, Fatima Sana Shaikh, Sanya Malhotra IMDb Rating: 8.3/10
If there is one thing the legendary Aamir Khan knows how to do is, capture a damn good story. In this film, Aamir Khan plays a former wrestler turned relentless coach, training his daughters to defy gender norms and dominate in a sport no one expected them to touch. Dangal is built on discipline, vision, and pushing past every “no” society throws your way. It’s not a business film, but the mindset? Pure founder energy. Build the system. Train the talent. Take the win no one thought you could.
Scott and Sid
Year: 2018 Directors: Scott Elliott, Sid Sadowskyj Stars: Tom Blyth, Richard Mason IMDb Rating: 6.6/10
Two misfit kids make a pact to do something extraordinary with their lives. But they actually follow through though. Based on the real-life story of the filmmakers, Scott and Sid is raw, awkward, and weirdly inspiring. No flashy moments, no Silicon Valley office montages. Just two guys slowly building a creative empire from a high school full of people who expected nothing from them. Every founder who started with zero connections and had to bootstrap belief into something real will get it.
Mongol
Year: 2007 Director: Sergei Bodrov Stars: Tadanobu Asano, Sun Honglei, Khulan Chuluun IMDb Rating: 7.2/10
This is Genghis Khan’s origin story, long before the empire, the battles, or the legend. Mongol focuses on the early years—captivity, betrayal, survival, and an almost maniacal sense of vision. If you can look past the swords, blood, and wild landscapes, this is really about long-term strategy, leadership under pressure, and building something from nothing in a world actively trying to destroy you. Ruthless? Yes. Entrepreneurial? Painfully.
The Internship
Year: 2013 Director: Shawn Levy Stars: Vince Vaughn, Owen Wilson, Rose Byrne IMDb Rating: 6.3/10
Check this: two out-of-work sales guys crash Google’s intern program, surrounded by coding prodigies half their age and twice their confidence. The Internship is chaotic, unrealistic, and kind of dumb. But that is the point! It is also weirdly valuable if you’ve ever felt completely out of place in a hyper-technical world. Beneath the comedy, there’s something real about learning to adapt, ask the right questions, and find your edge. It’s not a how-to on business building, but it is a reminder that soft skills and a refusal to quit still matter.
The Iron Lady
Year: 2011 Director: Phyllida Lloy Stars: Meryl Streep, Jim Broadbent, Richard E. Grant IMDb Rating: 6.4/10
The biographical film about Margaret Thatcher, the first female Prime Minister of the UK, dives into her political career and personal challenges. It’s an inspiring story of leadership, determination, and breaking barriers which bags its place in our list.
The Secret Life of Walter Mitty
Year: 2013 Director: Ben Stiller Stars: Ben Stiller, Kristen Wiig, Jon Daly IMDb Rating: 7.3/10
This is a movie about someone who’s spent most of his life waiting and then decides not to. Walter Mitty works a dull job, zones out constantly, and avoids anything that might actually change him. Until one day he doesn’t. It’s not a business film, but if you’ve ever stalled out on a good idea or talked yourself out of trying something, this will hit. Sometimes the biggest shift is getting out of your own way.
The Social Dilemma
Year: 2020 Director: Jeff Orlowski Stars: Tristan Harris, Jeff Seibert, Bailey Richardson IMDb Rating: 7.6/10
This isn’t a movie you watch for business tips—it’s one you watch to realize the business model is you. The Social Dilemma pulls back the curtain on how the platforms we depend on are built to keep us addicted, distracted, and easy to sell. It features former execs from companies like Google, Facebook, and Twitter admitting just how bad it’s gotten. For entrepreneurs, it’s a brutal reminder that how you monetize attention matters just as much as what you build.
The Theory of Everything
Year: 2014 Director: James Marsh Stars: Eddie Redmayne, Felicity Jones, Tom Prio IMDb Rating: 7.7/10
Stephen Hawking’s life wasn’t driven by luck, funding rounds, or public speaking gigs. It was built through sustained intellectual obsession all done under extreme pressure, with a clock ticking inside his body. The Theory of Everything is not about invention in the startup sense, but it’s absolutely about creating something lasting against all odds. The kind of focus, adaptation, and sheer force of will Hawking had to summon is what most people glamorize in founders but rarely understand. If your work means enough to you to keep going when everything else collapses—that’s the thread this movie pulls.
The Truman Show
Year: 1998 Director: Peter Weir Stars: Jim Carrey, Ed Harris, Laura Linney IMDb Rating: 8.1/10
Truman’s entire life is a product—one he didn’t ask to be part of. Everyone around him is acting. Every choice he makes is framed. And somewhere deep in the artificial calm, he starts to notice the cracks. It’s about the moment you realize the world you’re operating in wasn’t designed for your freedom. The only way forward is through a door no one told you existed.
War Dogs
Year: 2016 Director: Todd Phillips Stars: Jonah Hill, Miles Teller, Steve Lantz IMDb Rating: 7.1/10
Two guys in their twenties land a $300 million Pentagon contract to supply weapons to the U.S. military. No, really. Jonah Hill’s character is a walking red flag in a Gucci belt, and Miles Teller is just trying to keep up. This is a movie about scale without ethics, confidence without competence, and what happens when the business outgrows the hustle. It’s hilarious—until it isn’t.
We Bought a Zoo
Year: 2011 Director: Cameron Crowe Stars: Matt Damon, Scarlett Johansson, Thomas Haden Church IMDb Rating: 7.1/10
A single father decides to buy and renovate a struggling zoo, providing a fresh start for his family. This heartwarming story highlights the importance of perseverance, family, and following one’s dreams. Definitely worth a watch.
No one’s safe in this movie. Not the drummer, not the teacher, not your nervous system. Whiplash is all sweat, blood, and psychological warfare set to a jazz soundtrack that only gets louder the closer you get to collapse. The pace is relentless. J.K. Simmons turns verbal abuse into an art form, and Miles Teller unravels on screen with the kind of focus that makes ambition look like a mental illness. It’s not about dreams, it’s about obsession, and what happens when there’s no line between “getting better” and completely losing control. If you’re chasing greatness and haven’t snapped yet, this’ll make your palms sweat.
Yes Man
Year: 2008 Director: Peyton Reed Stars: Jim Carrey, Zooey Deschanel, Bradley Cooper IMDb Rating: 6.8/10
Jim Carrey plays a guy whose entire life is stuck in neutral until he starts saying yes to everything. Obviously, the result is exactly as stupid, chaotic, and occasionally brilliant as you’d expect. He says yes to Korean language classes. Yes to bungee jumping. Yes to random startup schemes and Red Bull-fueled productivity cults. It’s ridiculous, but there’s something quietly valuable buried in all the mess: momentum. Yes Man is about what happens when you stop filtering yourself out of your own future. And if you’re the kind of entrepreneur who overthinks every move, this is the slap in the face you probably need.
Any Given Sunday
Year: 2005 Director: Oliver Stone Stars: John Beard, Tim Belden, Barbara Boxer IMDb Rating: 7.6/10
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
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
Everyone’s desperate, everyone’s lying, and no one’s getting the good leads. Glengarry Glen Ross is a brutal, talk-heavy pressure cooker about real estate salesmen clawing for their next commission. Alec Baldwin shows up for five minutes and delivers the most aggressive monologue in business cinema history. Coffee is for closers, hope is for amateurs. If you’re in sales, this is either your favorite movie or your worst nightmare. If you’re not, it’s a reminder that selling anything—ideas, products, yourself—comes at a cost.
It’s a Wonderful Life
Year: 1946 Director: Frank Capra Stars: James Stewart, Donna Reed, Lionel Barrymore IMDb Rating: 8.6/10
On the surface, it’s a Christmas movie. But really, It’s a Wonderful Life is about burnout, legacy, and what it means to build something meaningful when it feels like the world’s stacked against you. George Bailey isn’t a founder, but he is a community builder who sacrifices fast wins for long-term impact—and nearly loses himself in the process. It’s old, yes. Sentimental, definitely. But underneath it all is a message every founder needs: what you’re building might matter more than you think.
Molly Bloom went from Olympic-level skier to running the most exclusive underground poker empire in the world. Molly’s Game is fast, sharp, and full of the kind of risk you can’t spreadsheet. Jessica Chastain delivers pure control while everything around her burns. Founders who’ve bet big without a safety net will get it.
Tommy Boy
Year: 1995 Director: Peter Segal Stars: Chris Farley, David Spade, Bo Derek IMDb Rating: 7.1/10
Total chaos. Zero business skills. Heart in the right place. Somehow—it works. Tommy Boy is a screwball comedy about trying to save a family company through sheer stubbornness and charm. Chris Farley is a disaster of a salesman, but he learns (sort of), grows (barely), and makes it work (chaotically). Under the slapstick, it’s actually a solid lesson: connection beats polish, and sincerity can close a deal even when your pitch is falling apart.
Adam Sandler plays a burned-out scout who bets everything on one overlooked basketball player—and goes all in to get him to the NBA. Hustle is about belief, mentorship, and rebuilding from failure. It’s not tech, but the entrepreneurial spirit is everywhere: taking a long shot, building trust, and grinding through every no. Sandler gives one of his best performances, and the message lands clean: if you believe in someone—or something—build until it becomes undeniable.
Rush
Year: 2013 Director: Ron Howard Stars: Chris Hemsworth, Daniel Brühl IMDb Rating: 8.1/10 Available on: Prime Video, Apple TV
Rush is a fierce rivalry between two Formula 1 legends: the reckless showman James Hunt and the precision-obsessed Niki Lauda. It’s about competition at the highest level—where obsession, perfection, and ego all collide. This is startup warfare with race cars. It’s about finding your edge, protecting it, and learning that discipline often beats flash when everything’s on the line.
Pad Man
Year: 2018 Director: R. Balki Stars: Akshay Kumar, Radhika Apte, Sonam Kapoor IMDb Rating: 7.9/10
Pad Man tells the story of Arunachalam Muruganantham, who invented low-cost sanitary pads for rural India—and was ridiculed, ostracized, and nearly ruined for it. It’s not just a story of innovation—it’s about building for people who are always excluded from the business conversation. If your startup claims to be purpose-driven, this is the standard.
Ranbir Kapoor plays a quiet guy who gets written off by corporate culture and decides to start his own sales company—inside the one he works for. Rocket Singh is about ethics, innovation, and figuring out how to build something honest in an industry built on nonsense. It’s low-key, funny, and sharper than it looks. Founders tired of faking enthusiasm for broken systems will feel this one.
Becoming Warren Buffett
Year: 2017 Director: Peter W. Kunhardt Starring: Warren Buffett (documentary) IMDb Rating: 7.5/10
Becoming Warren Buffett is less about money and more about clarity—how to stay focused, grounded, and aligned with your values while the world spins faster around you. Quiet, thoughtful, and mandatory for anyone playing the long game.
Middle Men
Year: 2009 Director: George Gallo Stars: Luke Wilson, Giovanni Ribisi, Gabriel Macht IMDb Rating: 6.8/10
Before Stripe, before PayPal, there were these guys—accidentally inventing online payment processing while knee-deep in adult content, mob threats, and coke-fueled incompetence. Middle Men is the story of how the internet monetized itself when no one was watching, and how one “legit” businessman tried to clean it up while still getting paid. It’s funny, chaotic, and feels like someone filmed a startup pitch in a strip club bathroom. The tech is real, the money is insane, and the fallout is exactly what happens when growth outpaces control.
MoneyBall
Year: 2011 Director: Bennett Miller Stars: Brad Pitt, Robin Wright, Jonah Hill IMDb Rating: 7.6/10
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? Billy Beane, the maverick General Manager of the Oakland A’s. 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
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.
There Will Be Blood
Year: 2007 Director: Paul Thomas Anderson Stars: Daniel Day-Lewis, Paul Dano, Dillon Freasier IMDb Rating: 8.2/10
This one isn’t inspirational, it’s more. It’s power, greed, and capitalism at its most feral. Daniel Day-Lewis plays Daniel Plainview, an oilman who will charm, manipulate, and bulldoze his way to dominance. There Will Be Blood is slow, brutal, and soaked in ambition so intense it becomes violent. If you’re building something and think success is only about pitch decks and networking—this film will remind you what it looks like when the desire to win becomes its own monster.
Willy Wonka & the Chocolate Factory
Year: 1971 Director: Mel Stuart Stars: Gene Wilder, Peter Ostrum, Jack Albertson IMDb Rating: 7.8/10
Dear reader, are you surprised? I hope, at least a little. Underneath the whimsy and literal rivers of chocolate, Willy Wonka is a visionary founder running a company with zero HR, questionable safety practices, and a brand so iconic it still dominates shelves decades later. Gene Wilder’s Wonka is eccentric, unpredictable, and obsessed with legacy—handing the keys to the factory only to someone who truly gets it. For entrepreneurs, it’s a strangely useful metaphor: build weird, build bold, and trust no one who lacks imagination. Don’t be afraid to be your bold self, dear reader.
Erin Brockovich
Year: 2000 Director: Steven Soderbergh Stars: Julia Roberts, Albert Finney, Aaron Eckhart IMDb Rating: 7.4/10
We do love a movie that justly represents what women are capable of. This is one of them legends. No law degree, no connections—just an out-of-work single mom who takes down a giant utility company through grit, research, and the kind of persistence that most people burn out on. Oh and that mother: Julia Fricking Robert’s. Erin Brockovich is about impact, not empire. Julia herself plays her with so much raw honesty it almost feels like a documentary. It’s not about scaling a business—it’s about building credibility from scratch and refusing to be dismissed. The kind of entrepreneurial mindset that doesn’t need funding to be powerful.
Silicon Cowboys
Year: 2016 Director: Jason Cohen Stars: Rod Canion, Jim Harris, Bill Murto IMDb Rating: 6.9/10
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
This show understands startups too well, right down to the awkward founders, the inflated valuations, and the whiteboard delusions. Silicon Valley follows a group of socially malfunctioning engineers trying to build a company without selling their souls (or accidentally tanking their own product). It’s ruthless about tech culture. Entrepreneurs will see themselves in the good, the bad, and the glitchy—and if they’re honest, maybe in the pivoting disaster too. It’s all here. Every awkward pitch. Every stupid metric. Every accidental billion.
Steve Jobs: The Lost Interview
Year: 2012 Director: Paul Sen Stars: Robert X. Cringely, Steve Jobs IMDb Rating: 8.0/10
No edits, no theatrics, just 70 minutes of direct insight on creativity, product design, leadership, and why most people in business have no idea what they’re doing. It’s raw. And it’s wildly useful if you’re building something and need to be reminded that vision without execution is just marketing fluff. Watch this if you care more about building something real than being liked while you do it.
Thank You for Smoking
Year: 2005 Director: Jason Reitman Stars: Aaron Eckhart, Cameron Bright, Maria Bello IMDb Rating: 7.5/10
Forget Steve Jobs and Mark Zuckerberg. 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: 2004 Director: Martin Scorsese Stars: Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale IMDb Rating: 7.5/10
Fasten your seatbelts, because we’re taking a flight into the captivating world of Howard Hughes in Martin Scorsese’s epic biopic. 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
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
Elizabeth Holmes wanted to change the world. Instead, she built a billion-dollar fantasy powered by lies, charisma, and a voice she may or may not have faked. The Dropout is a dramatized look at Theranos. Amanda Seyfried plays Holmes with eerie precision: not quite a villain, not quite a victim—just a founder who couldn’t afford to fail and didn’t know how to stop pretending. For entrepreneurs, it’s a lesson in the dark side of hype, the danger of unchecked confidence, and how “fake it till you make it” stops working when lives are on the line.
The Donut King
Year: 2020 Director: Alice Gu Stars: Ted Ngoy, Christie Suganthini, Chet Ngoy IMDb Rating: 7.1/10
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
Forget everything you thought you knew about the golden arches.The Founder is 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
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
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, namely Facebook.
“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!
Wall Street
Year: 1987 Director: Oliver Stone Stars: Charlie Sheen, Michael Douglas, Tamara Tunie IMDb Rating: 7.3/10
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 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” 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.
All of these movies about entrepreneurship provide diverse stories, from inspiring biographical dramas to insightful documentaries. They capture the essence of the entrepreneurial journey, showcasing the creativity, resilience, and determination needed to turn dreams into reality. Whether you’re seeking motivation, a new perspective, or an entertaining watch, these films offer valuable lessons and inspiration for anyone on their entrepreneurial path.
The entrepreneurship journey is a thrilling blend of creativity, risk, and perseverance. These top movies about entrepreneurship entertain and provide invaluable insights and motivation for anyone looking to embark on or continue their 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.
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