51 Best Movies for Entrepreneurs Must Watch

Jobs Movie Poster

Jobs (2013)

Entrepreneur: Steve Jobs
Director: Joshua Michael Stern
Starring: Steve Jobs is portrayed by Ashton Kutcher, with Josh Gad as Apple Computer’s co-founder Steve Wozniak.
Synopsis: Based on the life of Steve Jobs, from 1974 while a student at Reed College to the introduction of the iPod in 2001.

Thank You for Smoking Movie Poster

Thank You for Smoking (2005)

Director: Jason Reitman
Starring: Aaron Eckhart, Maria Bello, Cameron Bright, Adam Brody, Sam Elliott, Katie Holmes, Rob Lowe, William H. Macy, J. K. Simmons, Robert Duvall
Synopsis: Based on the 1994 satirical novel of the same name by Christopher Buckley. It follows the efforts of Big Tobacco’s chief spokesman, Nick Naylor, who lobbies on behalf of cigarettes using heavy spin tactics while also trying to remain a role model for his 12-year-old son.

Fight Club Movie Poster

Fight Club (1999)

Director: David Fincher
Starring: Brad Pitt, Edward Norton, and Helena Bonham Carter
Synopsis: Based on the 1996 novel of the same name by Chuck Palahniuk. Edward Norton plays the unnamed narrator, who is discontented with his white-collar job. He forms a “fight club” with soap salesman Tyler Durden (Brad Pitt) and becomes embroiled in a relationship with an impoverished but beguilingly attractive woman, Marla Singer (Helena Bonham Carter).

Enron The Smartest Guys in the Room Movie Poster

Enron: The Smartest Guys in the Room (2005)

Director: Alex Gibney
Starring: Peter Coyote (narrator)
Synopsis: Based on the best-selling 2003 book of the same name by Fortune reporters Bethany McLean and Peter Elkind, who are credited as writers of the film alongside the director, Alex Gibney. It examines the 2001 collapse of the Enron Corporation, which resulted in criminal trials for several of the company’s top executives during the ensuing Enron scandal, and contains a section about the involvement of Enron traders in the 2000-01 California electricity crisis. Archival footage is used alongside new interviews with McLean and Elkind, several former Enron executives and employees, stock analysts, reporters, and former Governor of California Gray Davis.

Office Space Movie Poster

Office Space (1999)

Director: Mike Judge
Starring: Ron Livingston, Jennifer Aniston, Gary Cole, Stephen Root, David Herman, Ajay Naidu, and Diedrich Bader.
Synopsis: It satirizes the work life of a typical 1990s software company, focusing on a handful of individuals weary of their jobs.

Molly's Game movie Poster

Molly’s Game (2017)

Entrepreneur: Molly Bloom
Director: Aaron Sorkin
Starring: Jessica Chastain, Idris Elba, Kevin Costner, Michael Cera, Jeremy Strong, Chris O’Dowd, Joe Keery, Brian D’Arcy James, and Bill Camp
Synopsis: Based on the 2014 memoir of the same name by Molly Bloom. The film follows Molly Bloom (Jessica Chastain), who becomes the target of an FBI investigation after the underground poker empire she runs for Hollywood celebrities, athletes, business tycoons, and the Russian mob is exposed.

War Dogs movie Poster

War Dogs (2016)

Entrepreneur: Efraim Diveroli and David Packouz
Director: Todd Phillips
Starring: Jonah Hill, Miles Teller, Ana de Armas, Bradley Cooper
Synopsis: The film follows two arms dealers, Efraim Diveroli and David Packouz, who receive a U.S. Army contract to supply ammunition for the Afghan National Army worth approximately $300 million. The film, which has an unreliable narrator, is heavily fictionalized and dramatized, and some of its events, such as the duo driving through Iraq, were either invented or based on other events, such as screenwriter Stephen Chin’s own experiences.

Wall Street Money Never Sleeps Movie Poster

Wall Street: Money Never Sleeps (2010)

Director: Oliver Stone
Starring: Michael Douglas, Shia LaBeouf, Josh Brolin, Carey Mulligan, Frank Langella, Susan Sarandon, Eli Wallach
Synopsis: A sequel to Wall Street (1987). Now out of prison but still disgraced by his peers, Gordon Gekko works with his future son-in-law, an idealistic stock broker, when he sees an opportunity to take down a Wall Street enemy and rebuild his empire.

The Goods Live Hard, Sell Hard movie Poster

The Goods: Live Hard, Sell Hard (2009)

Director: Neal Brennan
Starring: Jeremy Piven, Ving Rhames, James Brolin, David Koechner, Kathryn Hahn, Ed Helms, Jordana Spiro and Craig Robinson
Synopsis: Used-car liquidator Don Ready is hired by a flailing auto dealership to turn their Fourth of July sale into a majorly profitable event.

There Will Be Blood Movie Poster

There Will Be Blood (2007)

Director: Paul Thomas Anderson
Starring: Daniel Day-Lewis, Paul Dano, Kevin J. O’Connor, Ciarán Hinds, and Dillon Freasier
Synopsis: A story of family, religion, hatred, oil, and madness, focusing on a turn-of-the-century prospector in the early days of the business. The film is loosely based on the 1927 novel Oil! by Upton Sinclair.

It’s a Wonderful Life Movie Poster

It’s a Wonderful Life (1946)

Director: Frank Capra
Starring: James Stewart, Donna Reed, Lionel Barrymore, Thomas Mitchell, Henry Travers, Beulah Bondi, Ward Bond, Frank Faylen, Gloria Grahame
Synopsis: It is based on the short story and booklet “The Greatest Gift” self-published by Philip Van Doren Stern in 1943, which itself is loosely based on the 1843 Charles Dickens novella A Christmas Carol. James Stewart as George Bailey, a man who has given up his personal dreams in order to help others in his community and whose thoughts of suicide on Christmas Eve bring about the intervention of his guardian angel, Clarence Odbody. Clarence shows George all the lives he touched and what the world would be like if he had not existed.

Any Given Sunday movie Poster

Any Given Sunday (1999)

Director: Oliver Stone
Starring: Al Pacino, Cameron Diaz, Dennis Quaid, Jamie Foxx, James Woods, LL Cool J, Ann-Margret, Lauren Holly, Matthew Modine, John C. McGinley, Charlton Heston, Bill Bellamy, Lela Rochon, Aaron Eckhart, Elizabeth Berkley
Synopsis: A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them. It is partly based on the 1984 novel On Any Given Sunday by NFL defensive end Pat Toomay; the title is derived from a line in the book (also used in the film) that a team can win or lose on “any given Sunday”, said by the fictitious coach Tony D’Amato.

Fyre Movie Poster

Fyre: The Greatest Party That Never Happened (2019)

Founders: Billy McFarland, Ja Rule
Director: Chris Smith
Synopsis: The film is about Billy McFarland and the failed Fyre Festival of 2017.

The Inventor Out for Blood in Silicon Valley Movie Poster

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

Entrepreneur: Elizabeth Holmes
Director: Alex Gibney
Synopsis: The story of Theranos, a multi-billion dollar tech company, its founder Elizabeth Holmes, the youngest self-made female billionaire, and the massive fraud that collapsed the company. It is considered a companion piece to the book, Bad Blood: Secrets and Lies in a Silicon Valley Startup.

Willy Wonka & the Chocolate Factory movie Poster

Willy Wonka & the Chocolate Factory (1971)

Director: Mel Stuart
Starring: Gene Wilder as candymaker Willy Wonka
Synopsis: Based on his 1964 novel Charlie and the Chocolate Factory. The film tells the story of a poor child named Charlie Bucket (Peter Ostrum) who, upon finding a Golden Ticket in a chocolate bar, wins the chance to visit Willy Wonka’s chocolate factory along with four other children from around the world.

The Great Hack Movie Poster

The Great Hack (2019)

Director: Karim Amer and Jehane Noujaim
Starring: Carole Cadwalladr, David Carroll, Brittany Kaiser, Julian Wheatland, Roger McNamee, Christopher Wylie
Synopsis: The film about the Facebook–Cambridge Analytica data scandal.

Becoming Warren Buffett movie Poster

Becoming Warren Buffett (2017)

Entrepreneur: Warren Buffett
Director: Peter W. Kunhardt
Synopsis: The legendary investor started out as an ambitious, numbers-obsessed boy from Nebraska and ended up becoming one of the richest and most respected men in the world.

Trading Places Movie Poster

Trading Places (1983)

Director: John Landis
Starring: Dan Aykroyd, Eddie Murphy, Ralph Bellamy, Don Ameche, Denholm Elliott, Jamie Lee Curtis
Synopsis: The film tells the story of an upper-class commodities broker (Aykroyd) and a poor street hustler (Murphy) whose lives cross when they are unwittingly made the subjects of an elaborate bet to test how each man will perform when their life circumstances are swapped.

Tommy Boy movie Poster

Tommy Boy (1995)

Director: Peter Segal
Starring: Chris Farley and David Spade
Synopsis: It tells the story of a socially and emotionally immature man (Farley) who learns lessons about friendship and self-worth, following the sudden death of his industrialist father.

The Corporation movie Poster

The Corporation (2003)

Director: Mark Achbar and Jennifer Abbott
Synopsis: The documentary examines the modern corporation. Bakan wrote the book The Corporation: The Pathological Pursuit of Profit and Power during the filming of the documentary.

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