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The Top 50 Movies All Startup Founders Must Watch

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By Keaton Aliabadi

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Introduction:

Here we rank (based on a combined metric of relevancy and Rotten Tomatoes score) the top 50 movies that all startup founders must watch along with a short clip from the movie, a description of the movie, and an explanation of why it's a must-see for entrepreneurs.

Let us know in the comments your opinion of this list and if we missed one! Without further ado, let's start with number 1 on the list.

1. The Social Network (2010)

What it’s about:

“The Social Network” explores the moment at which Facebook, the most revolutionary social phenomena of the new century, was invented — through the warring perspectives of the super-smart young men who each claimed to be there at its inception. The result is a drama rife with both creation and destruction; one that audaciously avoids a singular POV, but instead, by tracking dueling narratives, mirrors the clashing truths and constantly morphing social relationships that define our time. Drawn from multiple sources, the film captures the visceral thrill of the heady early days of a culture-changing phenomenon in the making — and the way it both pulled a group of young revolutionaries together and then split them apart.

Rotten Tomatoes Score:

The social network rotten tomato score

Relevancy Score: 10

Why Startup Founders Should Watch It: At the core, this is a relationship movie and a relationship movie about the relationship between founders at that. Sometimes relationships make or break startups more than the numbers or the product. Startups are made of people and the people part is very, very important.

Final Score: 98

2. Glengarry Glen Ross (1992)

What it’s about: David Mamet’s award-winning play about a group of desperate real estate agents comes to the big screen from director James Foley. In a role created specifically for the movie, Alec Baldwin appears as a sales motivator, informing the group of hard-luck salesmen that they must compete in a sales contest where the losers will be fired. The agents work their same tired leads, until one hatches a scheme to burglarize the office, steal the leads, and sell them to a rival. Featuring a cast that includes Al Pacino as the office’s sales leader, Jack Lemmon as an elderly loser, Alan Arkin and Ed Harris as frustrated salesmen, Kevin Spacey as the harassed office manager, and Jonathan Pryce as a client, Glengarry Glen Ross is, at its core, a character study about a group of men whose time has passed.

Rotten Tomatoes Score:

Glengarry glen ross rotten tomato score

Relevancy Score: 10

Why Startup Founders Should Watch It: Coffee is for closers! This is hands down the greatest sales movie ever created (and the most quoted). If you are in the startup game, you are in the sales game (you are selling yourself, selling your startup, selling a dream to your employees, etc.). This is a must watch.

Final Score: 97.5

3. Enron: The Smartest Guys in the Room (2005)

What it’s about:

Alex Gibney, who wrote and produced Eugene Jarecki’s The Trials of Henry Kissinger, examines the rise and fall of an infamous corporate juggernaut in Enron: The Smartest Guys in the Room, which he wrote and directed. The film, based on the book by Fortune Magazine reporters Bethany McLean and Peter Elkind, opens with a reenactment of the suicide of Enron executive Cliff Baxter, then travels back in time, describing Enron chairman Kenneth Lay’s humble beginnings as the son of a preacher, his ascent in the corporate world as an “apostle of deregulation,” his fortuitous friendship with the Bush family, and the development of his business strategies in natural gas futures. The film points out that the culture of financial malfeasance at Enron was evident as far back as 1987, when Lay apparently encouraged the outrageous risk taking and profit skimming of two oil traders in Enron’s Valhalla office because they were bringing a lot of money into the company. But it wasn’t until eventual CEO Jeff Skilling arrived at Enron that the company’s “aggressive accounting” philosophy truly took hold. The Smartest Guys in the Room explores the lengths to which the company went in order to appear incredibly profitable.

Rotten Tomatoes Score:

Relevancy Score: 9

Why Startup Founders Should Watch It: Enron was one of the most egregious and largest by the numbers cases of corporate corruption in history. How did it happen? How can it be prevented?

Final Score: 93.5

4. Steve Jobs (2015)

What it’s about:

Set backstage at three iconic product launches and ending in 1998 with the unveiling of the iMac, Steve Jobs takes us behind the scenes of the digital revolution to paint an intimate portrait of the brilliant man at its epicenter.

Rotten Tomatoes Score:

Relevancy Score: 10

Why Startup Founders Should Watch It: Hands down the best movie about Jobs. A look inside the man and his relationships. There is a certain type of startup founder that fights into the coming waves instead of fighting against them. 99.99% of these founders end up looking ridiculous (and broke), the others end up visionaries (and billionaires).

Final Score: 93

5. The Big Short (2015)

What it’s about: Writer/director Adam McKay joins forces with Paramount Pictures and Plan B Entertainment to adapt Michael Lewis’ best-seller The Big Short: Inside the Doomsday Machine, which centers on the housing a credit bubble of the 2000s.

Rotten Tomatoes Score:

The Big Short Rating

Relevancy Score: 9

Why Startup Founders Should Watch It: It was all fun and games until the world economy came crashing down. How did that happen? How can complexity and greed bring such a huge system crashing down. How can you avoid the same within your own organization? What’s your plan if the economy comes crashing down again? Definitely watch if you are in fintech.

Final Score: 89

6. Moneyball (2011)

What it’s about:

Based on a true story, Moneyball is a movie for anybody who has ever dreamed of taking on the system. Brad Pitt stars as Billy Beane, the general manager of the Oakland A’s and the guy who assembles the team, who has an epiphany: all of baseball’s conventional wisdom is wrong. Forced to reinvent his team on a tight budget, Beane will have to outsmart the richer clubs. The onetime jock teams with Ivy League grad Peter Brand (Jonah Hill) in an unlikely partnership, recruiting bargain players that the scouts call flawed, but all of whom have an ability to get on base, score runs, and win games. It’s more than baseball, it’s a revolution – one that challenges old school traditions and puts Beane in the crosshairs of those who say he’s tearing out the heart and soul of the game.

Rotten Tomatoes Score:

Moneyball Tomato Rating

Relevancy Score: 8

Why Startup Founders Should Watch It: One coach thought really, really hard about baseball and then, using statistics, changed the game. The same happened on Wall Street, the same will probably happen in your niche. What data could you be using to change your game, whatever it is? Definitely watch if you are in the sports industry.

Final Score: 87

7. Fyre: The Greatest Party That Never Happened (2019

What it’s about:

An exclusive behind the scenes look at the infamous unraveling of the Fyre music festival. Created by Billy McFarland and rapper Ja Rule, Fyre was promoted as a luxury music festival on a private island in the Bahamas featuring bikini-clad supermodels, A-List musical performances and posh amenities. Guests arrived to discover the reality was far from the promises.

Rotten Tomatoes Score:

Relevancy Score: 8

Why Startup Founders Should Watch It: Idiots committing fraud. Idiots raising huge, huge amounts of money. How did they raise so much money in the first place? What’s stopping me from raising that much money? Definitely watch if you are in the festival or music industry.

Final Score: 85.5

8. Pirates of Silicon Valley (1999)

What it’s about:

This tech-world biopic traces the fortunes of personal-computer companies Apple and Microsoft from their obscure dorm-room and backyard origins to their very public battle for corporate supremacy. Writer/director Martyn Burke follows the parallel lives of Microsoft founder Bill Gates (Anthony Michael Hall) and Apple co-founders Steve Jobs (Noah Wyle) and Steve Wozniak (Joey Slotnick) — the former a crafty Harvard dropout, the latter a pair of hippies with jobs at Hewlett-Packard and a yen to sell miniature versions of corporate mainframes to small businesses and at-home enthusiasts. Much like the personal-computer industry itself, the action starts with Apple then gradually shifts to Microsoft. The former plot thread recounts how Jobs and Wozniak “borrowed” key concepts from a Xerox computer lab, eked out their success as countercultural businessmen, and finally fell out with one another over the pressure of success. The latter thread focuses on the way Gates learned from, then surpassed, the brains behind Apple and turned his company into the global powerhouse that it is today. Based on Paul Freiberger and Michael Swaine’s Fire in the Valley: The Making of the Personal Computer, the film actually focuses only on that book’s final chapters. Produced for cable channel TNT, Pirates of Silicon Valley debuted June 18, 1999.

Rotten Tomatoes Score:

pirates of silicon valley tomato rating

Relevancy Score: 8

Why Startup Founders Should Watch It: Take a look back into the past at our predecessors. See their clever scheming and jockeying for power. I guess some things never change.

Final Score: 85

9. Jiro Dreams of Sushi (2012)

What it’s about:

Jiro Dreams of Sushi is the story of 85 year-old Jiro Ono, considered by many to be the world’s greatest sushi chef. He is the proprietor of Sukiyabashi Jiro, a 10-seat, sushi-only restaurant inauspiciously located in a Tokyo subway station. Despite its humble appearances, it is the first restaurant of its kind to be awarded a prestigious 3 star Michelin review, and sushi lovers from around the globe make repeated pilgrimage, calling months in advance and shelling out top dollar for a coveted seat at Jiro’s sushi bar.At the heart of this story is Jiro’s relationship with his eldest son Yoshikazu, the worthy heir to Jiro’s legacy, who is unable to live up to his full potential in his father’s shadow.

Rotten Tomatoes Score:

Relevancy Score: 7

Why Startup Founders Should Watch It: Jiro is a perfectionist and a relentless adherer to process. Jiro is also a life long learner and innovator in his world (Sushi). Definitely watch if you are in the restaurant or hospitality industry.

Final Score: 84.5

10. The Inventor: Out for Blood in Silicon Valley (2019)

What it’s about:

With a magical new invention that promised to revolutionize blood testing, Elizabeth Holmes became the world’s youngest self-made billionaire, heralded as the next Steve Jobs. Then, overnight, her $10-billion-dollar company dissolved. The rise and fall of Theranos is a window into the psychology of fraud.

Rotten Tomatoes Score:

Relevancy Score: 9

Why Startup Founders Should Watch It: Elizabeth Holmes once hailed as the greatest female entrepreneurs of all time is now facing prison time. What was her story and how did she do it? How did she fall? Definitely watch if you are in the biotech or health industries.

Final Score: 83.5

11. Margin Call (2011)

What it’s about: Set in the high-stakes world of the financial industry, Margin Call is an entangling thriller involving the key players at an investment firm during one perilous 24-hour period in the early stages of the 2008 financial crisis. When an entry-level analyst unlocks information that could prove to be the downfall of the firm, a roller-coaster ride ensues as decisions both financial and moral catapult the lives of all involved to the brink of disaster. Writer/director J.C. Chandor’s enthralling first feature is a stark and bravely authentic portrayal of the financial industry and its denizens as they confront the decisions that shape our global future.

Rotten Tomatoes Score: 

Margin Call Rotten Tomato Rating

Relevancy Score: 8

Why Startup Founders Should Watch It:

Another take on the 2008 financial crisis. This one takes a more somber tone. Great watch for the power dynamics at play within the firm as well as the greater economic lessons. Definitely watch if you are in fintech.

Final Score: 83.5

12. The American Meme (2018)

What it’s about:

With support from social media moguls DJ Khaled, Hailey Baldwin and Emily Ratajkowski, THE AMERICAN MEME explores the journeys of four distinct social media disruptors, Paris Hilton, Josh Ostrovsky (@TheFatJewish), Brittany Furlan & Kirill Bichutsky (@slutwhisperer), as they hustle to build empires out of their online footprints, redefining the paradigm for the American Dream.

Rotten Tomatoes Score:

The American Meme Rotten Tomato Score

Relevancy Score: 7

Why Startup Founders Should Watch It: Social media is a huge force and people have built entire businesses off of it. What do their lives look like and how did they do it? What drives social media traffic and how can it be harnessed? Definitely watch if you are in the social media industry.

Final Score: 82

13. Ex Machina (2015)

What it’s about:

Alex Garland, writer of 28 Days Later and Sunshine, makes his directorial debut with the stylish and cerebral thriller, EX MACHINA. Caleb Smith (Domhnall Gleeson), a programmer at an internet-search giant, wins a competition to spend a week at the private mountain estate of the company’s brilliant and reclusive CEO, Nathan Bateman (Oscar Isaac). Upon his arrival, Caleb learns that Nathan has chosen him to be the human component in a Turing Test-charging him with evaluating the capabilities, and ultimately the consciousness, of Nathan’s latest experiment in artificial intelligence. That experiment is Ava (Alicia Vikander), a breathtaking A.I. whose emotional intelligence proves more sophisticated–and more deceptive–than the two men could have imagined. 

Rotten Tomatoes Score:

Relevancy Score: 7

Why Startup Founders Should Watch It: A great and realistic portrayal of what a potential human or suprahuman AI may look like and come to be. Definitely watch if you are in the IoT industry or work with machine learning.

Final Score: 81

14. The Martian (2015)

What it’s about:

During a manned mission to Mars, Astronaut Mark Watney (Matt Damon) is presumed dead after a fierce storm and left behind by his crew. But Watney has survived and finds himself stranded and alone on the hostile planet. With only meager supplies, he must draw upon his ingenuity, wit and spirit to subsist and find a way to signal to Earth that he is alive. Millions of miles away, NASA and a team of international scientists work tirelessly to bring “the Martian” home, while his crewmates concurrently plot a daring, if not impossible rescue mission. As these stories of incredible bravery unfold, the world comes together to root for Watney’s safe return. Based on a best-selling novel, and helmed by master director Ridley Scott, THE MARTIAN features a star studded cast that includes Jessica Chastain, Kristen Wiig, Kate Mara, Michael Peña, Jeff Daniels, Chiwetel Ejiofor, and Donald Glover. 

Rotten Tomatoes Score:

Relevancy Score: 7

Why Startup Founders Should Watch It: Startup founders are masters of doing a lot with a little. But we are no comparison to astronaut Mark Watney. This is what is called “Extreme Bootstrapping.” Definitely watch if you are in the space travel or aeronautical industries.

Final Score: 80.5

15. The Founder (2017)

What it’s about:

Directed by John Lee Hancock (SAVING MR. BANKS), THE FOUNDER features the true story of how Ray Kroc (Michael Keaton), a struggling salesman from Illinois, met Mac and Dick McDonald, who were running a burger operation in 1950s Southern California. Kroc was impressed by the brothers’ speedy system of making the food and saw franchise potential. Writer Robert Siegel (THE WRESTLER) details how Kroc maneuvered himself into a position to be able to pull the company from the brothers and create a billion-dollar empire. The film also stars Laura Dern as Ray Kroc’s first wife Ethel; John Carroll Lynch as Mac McDonald and Nick Offerman as Dick McDonald.

Rotten Tomatoes Score:

The Founder Rotten Tomato Score

Relevancy Score: 8

Why Startup Founders Should Watch It: McDonalds, the billion dollar giant and the face of the fast food industry. How was it built? Definitely watch if you are in the food or restaurant industries.

Final Score: 80.5

16. Citizen Kane (1941)

What it’s about:

Following the death of publishing tycoon, Charles Foster Kane, reporters scramble to uncover the meaning of his final utterance; ‘Rosebud’.

Rotten Tomatoes Score:

Relevancy Score: 6

Why Startup Founders Should Watch It: A classic about legacy and building, and leaving behind, empires. An older movie but a must watch. Definitely watch if you are in the media or news industry.

Final Score: 80

17. Wall Street (1987)

What it’s about:

“Greed is Good.” This is the credo of the aptly named Gordon Gekko (Michael Douglas), the antihero of Oliver Stone’s Wall Street. Gekko, a high-rolling corporate raider, is idolized by young-and-hungry broker Bud Fox (Charlie Sheen). Inveigling himself into Gekko’s inner circle, Fox quickly learns to rape, murder and bury his sense of ethics. Only when Gekko’s wheeling and dealing causes a near-tragedy on a personal level does Fox “reform”-though his means of destroying Gekko are every bit as underhanded as his previous activities on the trading floor. Director Stone, who cowrote Wall Street with Stanley Weiser, has claimed that the film was prompted by the callous treatment afforded his stockbroker father after 50 years in the business; this may be why the film’s most compelling scenes are those between Bud Fox and his airline mechanic father (played by Charlie Sheen’s real-life dad Martin). Ironically, Wall Street was released just before the October, 1987 stock market crash.

Rotten Tomatoes Score:

Relevancy Score: 8

Why Startup Founders Should Watch It: Wall Street captures an era and an ethos of a money making machine. A great expose on greed and capitalism. Definitely watch if you are in fintech.

Final Score: 79

18. The Godfather (1972)

What it’s about:

Popularly viewed as one of the best American films ever made, the multi-generational crime saga The Godfather is a touchstone of cinema: one of the most widely imitated, quoted, and lampooned movies of all time. Marlon Brando and Al Pacino star as Vito Corleone and his youngest son, Michael, respectively. It is the late 1940s in New York and Corleone is, in the parlance of organized crime, a “godfather” or “don,” the head of a Mafia family. Michael, a free thinker who defied his father by enlisting in the Marines to fight in World War II, has returned a captain and a war hero. Having long ago rejected the family business, Michael shows up at the wedding of his sister, Connie (Talia Shire), with his non-Italian girlfriend, Kay (Diane Keaton), who learns for the first time about the family “business.” Nominated for 11 Academy Awards and winning for Best Picture, Best Actor (Marlon Brando), and Best Adapted Screenplay, The Godfather was followed by a pair of sequels. 

Rotten Tomatoes Score:

Relevancy Score: 6

Why Startup Founders Should Watch It: An absolute classic. If you like the firs one, watch the rest in the series. What makes people hold “power” in an organization. How do they keep “power.” What happens in an organization when its hierarchy is disrupted?

Final Score: 79

19. Spotlight (2015)

What it’s about:

SPOTLIGHT tells the riveting true story of the Pulitzer Prize-winning Boston Globe investigation that would rock the city and cause a crisis in one of the world’s oldest and most trusted institutions. When the newspaper’s tenacious “Spotlight” team of reporters delves into allegations of abuse in the Catholic Church, their year-long investigation uncovers a decades-long cover-up at the highest levels of Boston’s religious, legal, and government establishment, touching off a wave of revelations around the world. Directed by Academy Award-nominee Tom McCarthy, SPOTLIGHT is a tense investigative dramatic-thriller, tracing the steps to one of the biggest cover-ups in modern times.

Rotten Tomatoes Score:

Spotlight Rotten Tomato Score

Relevancy Score: 6

Why Startup Founders Should Watch It: What does deep, deeply rooted corruption in an organization look like? How is it rooted out? Watch one man unravel an organization of people who often have convinced themselves to look the other way. Definitely watch if you are in the media or news industry.

Final Score: 78.5

20. King Corn (2007)

What it’s about:

Ian Cheney and Curt Ellis, best friends from college on the east coast, move to the heartland to learn where their food comes from. With the help of friendly neighbors, genetically modified seeds, and powerful herbicides, they plant and grow a bumper crop of America’s most-productive, most-subsidized grain on one acre of Iowa soil. But when they try to follow their pile of corn into the food system, what they find raises troubling questions about how we eat–and how we farm.

Rotten Tomatoes Score:

king corn rotten tomato score

Relevancy Score: 6

Why Startup Founders Should Watch It: I hate to break it to you, but you are mostly made of corn. Definitely watch if you are in the farming, packaging, or food industries.

Final Score: 78

21. Food, Inc. (2009)

What it’s about:

In “Food, Inc.,” filmmaker Robert Kenner lifts the veil on our nation’s food industry, exposing the highly mechanized underbelly that’s been hidden from the American consumer with the consent of our government’s regulatory agencies, USDA and FDA. Our nation’s food supply is now controlled by a handful of corporations that often put profit ahead of consumer health, the livelihood of the American farmer, the safety of workers and our own environment. We have bigger-breasted chickens, the perfect pork chop, insecticide-resistant soybean seeds, even tomatoes that won’t go bad, but we also have new strains of e coli–the harmful bacteria that cause illness for an estimated 73,000 Americans annually. We are riddled with widespread obesity, particularly among children, and an epidemic level of diabetes among adults Featuring interviews with such experts as Eric Schlosser (Fast Food Nation), Michael Pollan (The Omnivore’s Dilemma) along with forward thinking social entrepreneurs like Stonyfield Farms’ Gary Hirschberg and Polyface Farms’ Joe Salatin, “Food, Inc.” reveals surprising–and often shocking truths–about what we eat, how it’s produced, who we have become as a nation and where we are going from here.

Rotten Tomatoes Score:

Relevancy Score: 6

Why Startup Founders Should Watch It: Food is an industry, a big one at that. Definitely watch if you are in the farming, packaging, or food industries.

Final Score: 77.5

22. Her (2013)

What it’s about:

Spike Jonze takes the helm for this comedy about a withdrawn writer (Joaquin Phoenix) who falls in love with his computer’s highly advanced operating system. 

Rotten Tomatoes Score:

Her Tomato Rating

Relevancy Score: 6

Why Startup Founders Should Watch It: As AI and “smart homes” become more and more prominent, where is this industry going? You will never look at Alexa the same… Definitely watch if you are in the IoT space.

Final Score: 77

23. Gattaca (1997)

What it’s about:

In a futuristic society where commerce has overridden more humanistic concerns, the rich and successful, eager to obtain physical and mental perfection, have taken to genetically engineering their off-spring. Such lab-created babies are known as Valids, while those conceived in the normal, loving fashion are In-Valids and are considered second-class citizens at best — especially if they have birth defects. Vincent (Ethan Hawke) is an In-Valid while his brother Anton (Loren Dean) is a Valid. The former brother is short, sickly, and bespectacled, while the latter brother is handsome, healthy and born to succeed. But though Anton seems close to perfection, he lacks the emotional flaws, passion, determination, desire and faith that motivate Vincent, whose strongest desire is to become a space navigator for the Gattaca Aerospace Corporation and travel on an upcoming mission to the moons of Saturn. Unfortunately, his birth status and a heart defect, relegate him to menial jobs. Unwilling to abandon hope, Vincent determinedly visits DNA broker German (Tony Shalhoub) who is able to create false identities for similar In-Valids. Set in an oppressive, bureaucratic and chillingly plausible early-21st-century world, Andrew Niccol’s sci-fi thriller differs from others in its focus on a morally ambiguous world and on characters rather than gizmos, technobabble and special effects.

Rotten Tomatoes Score:

Gattaca Rotten Tomato Score

Relevancy Score: 7

Why Startup Founders Should Watch It: Still holds up as the greatest biotech and genetic engineering movies of all time. Startlingly ahead of its time, definitely watch if you are in either of those industries.

Final Score: 76.5

24. Network (1976)

What it’s about:

When anchorman Howard Beale is forced to retire his 25-year post because of his age, he announces to his viewers that he’s going to commit suicide on his final program. When his announcement looks like it will improve the ratings, the entire event is turned into a garish entertainment spectacle.

Rotten Tomatoes Score:

Network Rotten Tomato Score

Relevancy Score: 6

Why Startup Founders Should Watch It: One of the most overlooked movies of all time. What could be happening in the media that’s not? This movie was way, way ahead of its time. Definitely watch if you are in the media or news industry.

Final Score: 76

25. The Wolf of Wall Street (2013)

What it’s about: Martin Scorsese directs the story of New York stockbroker Jordan Belfort. From the American dream to corporate greed, Belfort goes from penny stocks and righteousness to IPOs and a life of corruption in the late 80s. Excess success and affluence in his early twenties as founder of the brokerage firm Stratton Oakmont warranted Belfort the title “The Wolf of Wall Street.”

Rotten Tomatoes Score:

Critic Concensus

Relevancy Score: 7

Why Startup Founders Should Watch It: We’re making money baby! Jordan Belfort, one of the greatest swindlers of modern times. How did this man build an empire off of garbage. Sometimes a great product is not what it takes to IPO. Definitely watch if you are in fintech.

Final Score: 74.5

26. Boiler Room (2000)

What it’s about:

In this drama that explores greed and corruption in American business, Giovanni Ribisi plays Seth Davis, an intelligent and ambitious college dropout who runs a casino in his apartment. Eager to show his father that he can succeed, Seth lands a job with a small stock brokerage firm. He is given a space in the company’s “boiler room,” where he makes cold calls to prospective clients. As it turns out, Seth has a genuine talent for cold calling, which gains him the approval of his superiors, the admiration of his father, and the attentions of one of his co-workers, Abby Hilliard (Nia Long). However, the higher up the ladder Seth rises, the deeper he sinks into a quagmire of dirty dealings, until he’s breaking the law in order to keep his bosses happy and his paychecks coming. The Boiler Room also features Tom Everett Scott, Scott Caan, Jamie Kennedy, Nicky Katt, and Ben Affleck in a cameo as the headhunter who brings Seth into the firm. Ribisi and Scott also appeared together in That Thing You Do; Ribisi was the drummer replaced by Scott, who then led The One-Ders to fictional pop stardom.

Rotten Tomatoes Score: