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:

Boiler Room Tomatometer

Relevancy Score: 8

Why Startup Founders Should Watch It: Stocks, cold calling, dirty dealings. Wall street has a lot in common with the startup world. Another movie about greed on Wall Street. Definitely watch if you are in fintech.

Final Score: 73

27. Freakonomics (2010)

What it’s about:

FREAKONOMICS is the highly anticipated film version of the phenomenally bestselling book about incentives-based thinking by Steven Levitt and Stephen Dubner. Like the book, the film examines human behavior with provocative and sometimes hilarious case studies, bringing together a dream team of filmmakers responsible for some of the most acclaimed and entertaining documentaries in recent years: Academy Award (R) winner Alex Gibney (Enron: The Smartest Guys in the Room, Casino Jack and the United States of Money), Academy Award (R) nominees Rachel Grady and Heidi Ewing (Jesus Camp), Academy Award (R) nominee Morgan Spurlock (Super Size Me), Eugene Jarecki (Why We Fight) and Seth Gordon (The King of Kong).

Rotten Tomatoes Score:

freakonomics rotten tomato score

Relevancy Score: 8

Why Startup Founders Should Watch It: A great introduction to Freakonomics, one of the best resources to learn lessons on the economy and human behavior. If you like the movie, also check out their podcasts and books.

Final Score: 73

28. Goodfellas (1990)

What it’s about:

Martin Scorsese explores the life of organized crime with his gritty, kinetic adaptation of Nicolas Pileggi’s best-selling Wiseguy, the true-life account of mobster and FBI informant Henry Hill. Set to a true-to-period rock soundtrack, the story details the rise and fall of Hill, a half-Irish, half-Sicilian New York kid who grows up idolizing the “wise guys” in his impoverished Brooklyn neighborhood. He begins hanging around the mobsters, running errands and doing odd jobs until he gains the notice of local chieftain Paulie Cicero (Paul Sorvino), who takes him in as a surrogate son. As he reaches his teens, Hill (Ray Liotta) is inducted into the world of petty crime, where he distinguishes himself as a “stand-up guy” by choosing jail time over ratting on his accomplices. From that moment on, he is a part of the family. Along with his psychotic partner Tommy (Joe Pesci), he rises through the ranks to become Paulie’s lieutenant; however, he quickly learns that, like his mentor Jimmy (Robert DeNiro), his ethnicity prevents him from ever becoming a “made guy,” an actual member of the crime family. Soon he finds himself the target of both the feds and the mobsters, who feel that he has become a threat to their security with his reckless dealings. Goodfellas was rewarded with six Academy Award nominations including Best Picture; Pesci would walk away with Best Supporting Actor for his work. 

Rotten Tomatoes Score:

Goodfellas Rotten Tomato Score

Relevancy Score: 5

Why Startup Founders Should Watch It: Another great gangster movie. Watch for the power dynamics and organizational lessons.

Final Score: 73

29. Gravity (2013)

What it’s about:

Gravity stars Sandra Bullock and George Clooney in a heart-pounding thriller that pulls you into the infinite and unforgiving realm of deep space. Bullock plays Dr. Ryan Stone, a brilliant medical engineer on her first shuttle mission, with veteran astronaut Matt Kowalsky (Clooney). But on a seemingly routine spacewalk, disaster strikes. The shuttle is destroyed, leaving Stone and Kowalsky completely alone – tethered to nothing but each other and spiraling out into the blackness. The deafening silence tells them they have lost any link to Earth and any chance for rescue. As fear turns to panic, every gulp of air eats away at what little oxygen is left. But the only way home may be to go further out into the terrifying expanse of space. 

Rotten Tomatoes Score:

Relevancy Score: 5

Why Startup Founders Should Watch It: Another great movie about doing a lot with a little. Definitely watch if you are in the space travel or aeronautical industries.

Final Score: 73

30. Nightcrawler (2014)

What it’s about:

NIGHTCRAWLER is a pulse-pounding thriller set in the nocturnal underbelly of contemporary Los Angeles. Jake Gyllenhaal stars as Lou Bloom, a driven young man desperate for work who discovers the high-speed world of L.A. crime journalism. Finding a group of freelance camera crews who film crashes, fires, murder and other mayhem, Lou muscles into the cut-throat, dangerous realm of nightcrawling — where each police siren wail equals a possible windfall and victims are converted into dollars and cents. Aided by Rene Russo as Nina, a veteran of the blood-sport that is local TV news, Lou thrives. In the breakneck, ceaseless search for footage, he becomes the star of his own story.

Rotten Tomatoes Score:

Nightcrawler Rotten Tomato Score

Relevancy Score: 5

Why Startup Founders Should Watch It: What are people morbidly fascinated with and how does this turn into a business? How does interest drive revenue? What happens when you begin to rely on one employee whose motives are questionable at best… Definitely watch if you are in the media or news industry.

Final Score: 72.5

31. The Queen of Versailles (2012)

What it’s about:

The Queen of Versailles is a character-driven documentary about a billionaire family and their financial challenges in the wake of the economic crisis. With epic proportions of Shakespearean tragedy, the film follows two unique characters, whose rags-to-riches success stories reveal the innate virtues and flaws of the American Dream. The film begins with the family triumphantly constructing the biggest house in America, a 90,000 sq. ft. palace. Over the next two years, their sprawling empire, fueled by the real estate bubble and cheap money, falters due to the economic crisis. Major changes in lifestyle and character ensue within the cross-cultural household of family members and domestic staff. 

Rotten Tomatoes Score:

Relevancy Score: 5

Why Startup Founders Should Watch It: A great treatise on wealth and losing wealth. This one is a documentary so you get a real peak into the life of a super wealthy family. These people may look like your clients or maybe even a future you. Be careful.

Final Score: 72.5

32. The Kingmaker (2019)

What it’s about:

Centered on the indomitable character of Imelda Marcos, The Kingmaker examines, with intimate access, the Marcos family’s improbable return to power in the Philippines. The film explores the disturbing legacy of the Marcos regime and chronicles Imelda’s present-day push to help her son, Bongbong, win the vice-presidency. To this end, Imelda confidently rewrites her family’s history of corruption, replacing it with a narrative of a matriarch’s extravagant love for her country. In an age when fake news manipulates elections, Imelda’s comeback story serves as a dark fairy tale.

Rotten Tomatoes Score:

The Kingmaker Rotten Tomato Rating

Relevancy Score: 5

Why Startup Founders Should Watch It: How does news and social media influence the politics of a nation? How can news and social media be manipulated to change the story of a dynasty? What does real power look like? Definitely watch if you are in the news or media industry.

Final Score: 71.5

33. Jerry Maguire (1996)

What it’s about:

Jerry Maguire is a man who knows the score. As a top agent at Sports Management International, Jerry is unquestionably a master of his universe. Trouble is — Jerry’s mind, mouth and soul are usually on automatic pilot. He’s good at friendship, but (as his numerous ex-girlfriends testify) bad at intimacy. Still, there’s absolutely nothing wrong with Jerry that a sudden dose of failure can’t cure. A week after spontaneously writing a stirring, visionary mission statement for SMI entitled ‘The Things We Think And Do Not Say: The Future of Our Business,’ he’s unceremoniously fired. Stripped of his job and a good measure of his identity, the tenacious but hanging-by-a-thread Jerry is forced to start from scratch. He’s joined on his journey to redemption by two unlikely allies: Rod Tidwell, a second-tier wide receiver for the Arizona Cardinals; and Dorothy Boyd, a wistful 26-year-old single mother who departs her accountancy position with SMI for a very uncertain future with her new boss.

Rotten Tomatoes Score:

Relevancy Score: 6

Why Startup Founders Should Watch It: A rise and fall story about leveraging what you have and humility. Definitely watch if you are in the media, entertainment, or sports industries.

Final Score: 71.5

34. American Hustle (2013)

What it’s about:

A fictional film set in the alluring world of one of the most stunning scandals to rock our nation, American Hustle tells the story of brilliant con man Irving Rosenfeld (Christian Bale), who along with his equally cunning and seductive British partner Sydney Prosser (Amy Adams) is forced to work for a wild FBI agent Richie DiMaso (Bradley Cooper). DiMaso pushes them into a world of Jersey powerbrokers and mafia that’s as dangerous as it is enchanting. Jeremy Renner is Carmine Polito, the passionate, volatile, New Jersey political operator caught between the con-artists and Feds. Irving’s unpredictable wife Rosalyn (Jennifer Lawrence) could be the one to pull the thread that brings the entire world crashing down. Like David O. Russell’s previous films, American Hustle defies genre, hinging on raw emotion, and life and death stakes.

Rotten Tomatoes Score:

American Hustle Rotten Tomato Score

Relevancy Score: 5

Why Startup Founders Should Watch It: A very strong con movie. Like many con movies, has a lot of lessons about controlling appearances and controlling behavior for the purposes of persuasion. If you are a startup founder you are going to need a lot of persuasion

Final Score: 71

35. Molly's Game (2018)

What it’s about:

MOLLY’S GAME is based on the true story of Molly Bloom, an Olympic-class skier who ran the world’s most exclusive high-stakes poker game for a decade before being arrested in the middle of the night by 17 FBI agents wielding automatic weapons. Her players included Hollywood royalty, sports stars, business titans and finally, unbeknownst to her, the Russian mob. Her only ally was her criminal defense lawyer Charlie Jaffey, who learned that there was much more to Molly than the tabloids led us to believe.

Rotten Tomatoes Score:

Molly's Game Rotten Tomato

Relevancy Score: 6

Why Startup Founders Should Watch It: A story about building an unlikely business as an outsider. A story about crafting environments for your customers. Definitely watch if you are in the gambling industry.

Final Score: 71

36. The Disaster Artist (2017)

What it’s about:

The real life story of writer/director Tommy Wiseau, the man behind what is often referred to as “The Citizen Kane of Bad Movies,” The Room, is brought to life, chronicling the odd film’s troubled development and eventual cult success.

Rotten Tomatoes Score:

Relevancy Score: 5

Why Startup Founders Should Watch It: How do disasters and failure happen? Why don’t people see it coming? What do the relationships of the people involved look like? Definitely see if you are in the entertainment industry.

Final Score: 70.5

37. Office Space (1999)

What it’s about:

Peter Gibbons (Ron Livingston) is a computer programmer working for Initech in Houston. Every day, he and his friends Samir (Ajay Naidu) and Michael Bolton (David Herman as not THAT Michael Bolton), suffer endless indignities and humiliations in their soulless workspace from their soulless boss, Bill Lumbergh (Gary Cole). For Peter, stuck in his cookie-cutter apartment with paper-thin walls and IKEA furniture, every day is worse than the one before it — so every day is the worst of his life. To cap it off, Initech has hired a pair of “efficiency experts” to downsize the company. One Friday night, Peter’s soon to be ex-girlfriend Anne (Alexandra Wentworth) forces him to go to an occupational hypnotherapist to relieve work stress. 

Rotten Tomatoes Score:

Relevancy Score: 6

Why Startup Founders Should Watch It: A comedy about the drudgery of office life and escaping it. Hilariously quotable and will ring true with a lot of founders who escaped just the kind of monotony depicted.

Final Score: 70

38. Moon (2009)

What it’s about:

An astronaut miner extracting the precious moon gas that promises to reverse the Earth’s energy crisis nears the end of his three-year contract, and makes an ominous discovery in this psychological sci-fi film starring Sam Rockwell and Kevin Spacey. For three long years, Sam Bell has dutifully harvested Helium 3 for Lunar, a company that claims it holds the key to solving humankind’s energy crisis. As Sam’s contract comes to an end, the lonely astronaut looks forward to returning to his wife and daughter down on Earth, where he will retire early and attempt to make up for lost time. His work on the Selene moon base has been enlightening — the solitude helping him to reflect on the past and overcome some serious anger issues — but the isolation is starting to make Sam uneasy. With only two weeks to go before he begins his journey back to Earth, Sam starts feeling strange: he’s having inexplicable visions, and hearing impossible sounds. Then, when a routine extraction goes horribly awry, it becomes apparent that Lunar hasn’t been entirely straightforward with Sam about their plans for replacing him. The new recruit seems strangely familiar, and before Sam returns to Earth, he will grapple with the realization that the life he has created may not be entirely his own. Up there, hundreds of thousands of miles from home, it appears that Sam’s contract isn’t the only thing about to expire. 

Rotten Tomatoes Score:

Moon Rotten Tomato Score

Relevancy Score: 5

Why Startup Founders Should Watch It: What are the corporate and human resources of space travel? What resources are out there and how are we going to extract them? Definitely watch if you are in the space travel or resource extraction industries.

Final Score: 70

39. Becoming Warren Buffet (2017)

What it’s about:

A profile of Warren Buffett, CEO of the holding company Berkshire Hathaway, includes a look at his career as an investor and a philanthropist, and recollections of his personal and professional lives while speaking to high-school students in his native Omaha.

Rotten Tomatoes Score:

Relevancy Score: 7

Why Startup Founders Should Watch It: Warren Buffet produced disproportionate results with what he had. Very, very disproportionate results. What makes the man tick? Definitely watch if you are in fintech.

Final Score: 70

40. Blackfish (2013)

What it’s about:

Magnolia Pictures invites you and a guest to attend an advance screening of BLACKFISH, an eye-opening documentary directed by Gabriela Cowperthwaite. Many of us have experienced the excitement and awe of watching 8,000-pound orcas, or “killer whales,” soar out of the water and fly through the air at sea parks, as if in perfect harmony with their trainers. Yet, in our contemporary lore this mighty black-and-white mammal is like a two-faced Janus-beloved as a majestic, friendly giant yet infamous for its capacity to kill viciously. BLACKFISH unravels the complexities of this dichotomy, employing the story of notorious performing whale Tilikum, who-unlike any orca in the wild-has taken the lives of several people while in captivity. So what exactly went wrong? Shocking, never-before-seen footage and riveting interviews with trainers and experts manifest the orca’s extraordinary nature, the species’ cruel treatment in captivity over the last four decades, and the growing disillusionment of workers who were misled and endangered by the highly profitable sea-park industry. This emotionally wrenching, tautly structured story challenges us to consider our relationship to nature and reveals how little we humans have learned from these highly intelligent and enormously sentient fellow mammals.

Rotten Tomatoes Score:

Relevancy Score: 4

Why Startup Founders Should Watch It: A great movie on how we treat animals and animals in captivity. Definitely watch if you are in the pets or animal care industry.

Final Score: 69

41. The Master (2012)

What it’s about:

A striking portrait of drifters and seekers in post World War II America, Paul Thomas Anderson’s The Master unfolds the journey of a Naval veteran (Joaquin Phoenix) who arrives home from war unsettled and uncertain of his future – until he is tantalized by The Cause and its charismatic leader (Philip Seymour Hoffman).

Rotten Tomatoes Score:

The Master Rotten Tomato Score

Relevancy Score: 5

Why Startup Founders Should Watch It: How is your cult going? If you are running a startup you have more in common with cult founders than you might think. Watch a master of mass persuasion at the height of his craft.

Final Score: 67.5

42. The Talented Mr. Ripley (1997)

What it’s about:

After the Oscar-winning The English Patient, writer/director Anthony Minghella attempted another tricky literary adaptation with The Talented Mr. Ripley, which features heartthrob Matt Damon cast against type as a psychopathic bisexual murderer. Tom Ripley (Damon) is a bright and charismatic sociopath who makes his way in mid-’50s New York City as a men’s room attendant and sometimes pianist, though his real skill is in impersonating other people, forging handwriting, and running second-rate scams. After being mistaken for a Princeton student, Tom meets the shipping tycoon father of Dickie Greenleaf (Jude Law), who has traveled to the coast of Italy, where he’s living a carefree life with his father’s money and his beautiful girlfriend, Marge (Gwyneth Paltrow). Dickie’s father will pay Ripley 1,000 dollars plus his expenses if he can persuade Dickie to return to America. As Ripley and Dickie become friends, Tom finds himself both attracted to Dickie and envious of his life of pleasure. In time, he decides that he would rather be Dickie Greenleaf than Tom Ripley, so rather than go back to his life of poverty, Ripley impulsively murders Dickie and assumes his identity. The Talented Mr. Ripley was based on the first of a series of novels featuring Tom Ripley written by Patricia Highsmith; the story was previously filmed in 1960 as Purple Noon, with Alain Delon as Ripley.

Rotten Tomatoes Score:

the talented my ripley rotten tomato rating

Relevancy Score: 5

Why Startup Founders Should Watch It: Another treatise on persuasion and appearances. Sometimes the devil has glasses and a funny haircut.

Final Score: 66.5

43. Phantom Thread (2018)

What it’s about:

Set in the glamour of 1950’s post-war London, renowned dressmaker Reynolds Woodcock (Daniel Day-Lewis) and his sister Cyril (Lesley Manville) are at the center of British fashion, dressing royalty, movie stars, heiresses, socialites, debutants and dames with the distinct style of The House of Woodcock. Women come and go through Woodcock’s life, providing the confirmed bachelor with inspiration and companionship, until he comes across a young, strong-willed woman, Alma (Vicky Krieps), who soon becomes a fixture in his life as his muse and lover. Once controlled and planned, he finds his carefully tailored life disrupted by love. With his latest film, Paul Thomas Anderson paints an illuminating portrait both of an artist on a creative journey, and the women who keep his world running. Phantom Thread is Paul Thomas Anderson’s eighth movie, and his second collaboration with Daniel Day-Lewis.

Rotten Tomatoes Score:

phantom thread rotten tomato score

Relevancy Score: 4

Why Startup Founders Should Watch It: A look into the alluring world of fashion and a character study on obsession. Definitely watch if you are in the clothing or fashion industries.

Final Score: 65.5

44. Capote (2005)

What it’s about:

On assignment to write an article for ‘The New Yorker,’ Truman Capote traveled to a small Kansas town, where he began to investigate and report on the gruesome murder of a local family. At first leery of the writer, the townsfolk come to trust Capote and allow him into their lives, giving him his story.

Rotten Tomatoes Score:

Capote Rotten Tomato Score

Relevancy Score: 4

Why Startup Founders Should Watch It: A character study on a man whose personality was so strange and so powerful he is hard to forget. Watch for the flawless acting alone. Definitely watch if you are in the media or entertainment industry.

Final Score: 65

45. Casino (1995)

What it’s about:

The inner-workings of a corrupt Las Vegas casino are exposed in Martin Scorsese’s story of crime and punishment. The film chronicles the lives and times of three characters: “Ace” Rothstein (Robert De Niro), a bookmaking wizard; Nicky Santoro (Joe Pesci), a Mafia underboss and longtime best friend to Ace; and Ginger McKenna (Sharon Stone, in a role she was born to play), a leggy ex-prostitute with a fondness for jewelry and a penchant for playing the field. Ace plays by the rules (albeit Vegas rules, which, as he reminds the audience in voiceover, would make him a criminal in any other state), while Nicky and Ginger lie, cheat, and steal their respective ways to the top. The film’s first hour and a half details their rise to power, while the second half follows their downfall as the FBI, corrupt government officials, and angry mob bosses pick apart their Camelot piece by piece.

Rotten Tomatoes Score:

Relevancy Score: 5

Why Startup Founders Should Watch It: The most underrated gangster movie ever made. Hilarious and engaging, every character’s actions lead them on forever intertwining collision courses. Another movie about empire building and rise and falls. Definitely watch if you are in the gambling industry.

Final Score: 65

46. Existenz (1999)

What it’s about:

Set in the near-future, eXistenZ depicts a society in which game designers are worshipped as superstars and players can organically enter inside the games. At the center of the story is Allegra Geller whose latest games system eXistenZ taps so deeply into its users fears and desires that it blurs the boundaries between reality and escapism. When fanatics attempt to assassinate Allegra, she is forced to flee. Her sole ally is Ted Pikul (Law), a novice security guard who is sworn to protect her. Persuading Ted into playing the game, Allegra draws them both into a phantasmagoric world where existence ends and eXistenZ begins.

Rotten Tomatoes Score:

Existenz Rotten Tomato

Relevancy Score: 6

Why Startup Founders Should Watch It: A great sci fi movie about virtual reality and biotechnology. Definitely watch if you are in one of those two industries.

Final Score: 62

47. Magnolia (1999)

What it’s about:

An intriguing and entertaining study in characters going through varying levels of crisis and introspection. This psychological drama leads you in several different directions, weaving and intersecting various subplots and characters, from a brilliant Tom Cruise, as a self-proclaimed pied-piper, to a child forced to go on a TV game show and the pressures he faces from a ruthless father.

Rotten Tomatoes Score:

Relevancy Score: 4

Why Startup Founders Should Watch It: A great character study about what makes people tick. Look into the lives of different people and see why the ended up who they are doing what they are doing. Definitely watch if you are in any industry having to do with public speaking or often have to present.

Final Score: 61.5

48. Up in the Air (2009)

What it’s about:

Ryan Bingham, a corporate hatchet man who loves his life on the road, is forced to fight for his job when his company downsizes its travel budget. He is required to spend more time at home just as he is on the cusp of a goal he’s worked toward for years: reaching ten million frequent flyer miles and just after he’s met the frequent-traveler woman of his dreams.

Rotten Tomatoes Score:

Up in the Air Tomato Rating

Relevancy Score: 7

Why Startup Founders Should Watch It: A good movie about routine. Forming routine, escaping routine, questioning routine. Some other good business lessons sprinkled in as well.

Final Score: 61

49. Pi (1998)

What it’s about:

God and man and math: The tawdry meets the Talmudic in this complex thriller about a tortured computer genius trying to beat the stock market.

Rotten Tomatoes Score:

Pi Rotten Tomato Score

Relevancy Score: 3

Why Startup Founders Should Watch It: A movie about math and mental health. What secrets do numbers hold?

Final Score: 59

50. Primer (2004)

What it’s about:

The debut feature from filmmaker Shane Carruth — who wrote, directed, photographed, edited, scored, and stars — Primer is a psychological sci-fi thriller about a group of four tech entrepreneurs. Toiling away in a garage, the quartet have successfully created error-checking systems for their clients. But their recent work seems to have created an unexpected and seemingly impossible side-effect. Suddenly, two members of the group realize they are in possession of a device that can double, or perhaps even quadruple, the space-time continuum of anything that enters it. What at first seems like a windfall of astronomical proportions eventually proves to be much more than they bargained for, as the duo attempt to manipulate time to their financial — and emotional — benefit. Also starring Casey Gooden, Anand Upadhyaya, and Carrie Crawford, Primer premiered at the 2004 Sundance Film Festival, where it won the coveted Grand Jury Prize for dramatic film.

Rotten Tomatoes Score:

Primer Rotten Tomato Score

Relevancy Score: 4

Why Startup Founders Should Watch It: It is crazy what four guys in a garage can build. This movie is that idea taken to the extreme.

Final Score: 56.5

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