20+ Best Hollywood Movies Every Entrepreneur Must Watch

Entrepreneurship is a skill that you aren’t born with but you develop it with experience.

This experience could be gained from multiple sources such as working under a successful entrepreneur, starting and failing at different ventures, building a successful venture, or hustling through the hardships of life and overcoming each of them one by one.

While all these sources are practical and would help you grow with entrepreneurial skills such as leadership, team management, project and task management, organized work structure, goal settings, convincing others with your ideas, network building, and much more.

Well, there’s one more way to develop your entrepreneurial skills and that’s by watching movies. There are many Hollywood movies on Entrepreneurs and Entrepreneurship produced every year in the industry.

Most of these films create deep impact and teach important lessons on human behavior, leadership qualities, team building, gaining trust, and becoming a role model.

Today, we will look into some of the best Hollywood movies for entrepreneurs.

Best Hollywood Movies for Entrepreneurs

Entrepreneurship isn’t a job but it’s an art. Like every other art, you become an expert entrepreneur with practice and experience.

Nobody can become an overnight successful entrepreneur. It needs courage, dedication, persistence, and most importantly belief and hard work in their vision

Here are some of the best Hollywood movies for Entrepreneurs that try to teach just that.

Pirates of Silicon Valley (1999)

Pirates of Silicon Valley

Pirates of Silicon Valley is a made for television American biographical drama film based on the emergence of personal computers in Silicon Valley. The film features the rivalry between Jobs from Apple and Gates from Microsoft in their race to dominate in personal computer space.

It’s an interesting film and teaches you about the amount of work and heart put into a product that will be loved by everyone in the near future.

The Pursuit of Happyness (2006) 

The Pursuit of Happyness Film Biopic of chris gardner

Well, if you thought entrepreneurship dwells only in the IT industry and always thought it is all computers and luxurious home offices, then you must think again. The Pursuit of Happyness is a biographical Hollywood Motivational Film based on the one year struggle of the successful entrepreneur Chris Gardener being homeless in his early days with his son.

The film stars Will Smith as Chris Gardener and his real-life son Jaden Smith plays his son in the film as well. The film is about the real struggle and how life tests you and that’s the moment you either realize your true worth or you turn into another failure.

Office Space (1999)

office space 1999 film

Office Space is a 1999 American comedy film featuring a typical work culture of a software company in the later years of the 1990s. It tries to display the everyday struggles of the employees who are fed up with their monotonous jobs in the most humorous ways.

Directed by Mike Judge, the film is based on Judge’s Milton cartoon series.

Wall Street (1987)

Wall street movies about entreprenuer

Wall Street is a 1987 American drama film about a stock broker’s life, his greed for money, struggles, insider trading, and an eventual calling from his conscience.

The film is directed by Oliver Stone and stars Charlie Sheen as the young stock broker, whereas Michael Douglas plays the wealthy corporate raider and the main antagonist in the film. Douglas went on to win the Academy Award for Best Actor for his performance in the film.

Startup.com (2001)

movies for entrepreneur startup dot com

Startup.com is a 2001 documentary film about the ups and down of the dot-com startup firm called govWorks.com, that raised $60 million USD but didn’t survive in the long run.

Till date, the firm’s rise and fall are used as a reference because it taught some tough lessons during the late 90s when the internet bubble was bursting.

Boiler Room (2000)

Movies for entrepreneur Boiler Room in 2000

Directed by Ben Younger, Boiler Room is a 2000 American crime drama film that revolves around the life of stockbrokers.

The film is about a young man who enters the world of stock broking and eventually ends up on the wrong side of the law. Whether he is able to right the wrongs he has done is what forms the crux of the story.

Jerry Maguire (1996)

Jerry Maguire movies about business in Hollywood

Jerry Maguire is a sports Comedy film starring Tom Cruise in the titular role and Renee Zellweger as the female lead. Directed by Cameron Crowe, the film also stars Cuba Gooding Jr. who eventually won the Oscar for Best Actor in a Supporting Role for his work as Rodney Tidwell.

The Wolf of Wall Street (2013)

The Wolf of Wall Street based on true story

The Wolf of Wall Street is a biographical black comedy crime film based on the life of Jordan Belfort. Directed by Martin Scorsese, the film features Leonardo DiCaprio as Belfort and tells us the story of the rise of his career as a stockbroker, the ascent of his firm Stratton Oakmont and the ultimate downfall after he chooses the wrong side and gets engaged in corruption and fraud on Wall Street.

Forrest Gump (1994)

Forrest Gump emotional film

Directed by Robert Zemeckis, Forrest Gump is an excellent comedy-drama film adapted from a 1986 novel of the same name authored by Winston Groom. The film features Tom Hanks as the Forrest Gump who eventually goes on to win the Oscar for Best Actor for his performance in the film.

The film tells the story of a slow-witted but caring and athletically phenomenal man from Alabama. The film features different aspects of his life since his birth in 1944 until 1982 including various events.

Cocktail (1988)

Cocktail 1988 film for businessman in hollywood

Cocktail is a 1988 romantic comedy-drama film starring Tom Cruise, Bryan Brown, and Elisabeth Shue. Directed by Roger Donaldson, the film features a young business student named Brian Flanagan, played by Cruise, who is based in New York and has taken up bartending to raise money for college and his business venture.

Up in the Air (2009)

Up in the Air movie about business and money in hollywood

Up in the Air is a 2009 comedy-drama film starring George Clooney in the main lead. Directed by Jason Reitman, the film’s story is adapted from Walter Kirn’s novel of the same name. The film actually features the life of corporate downsizer Ryan Bingham, played by Clooney, and his travels.

Risky Business (1983)

movies for entrepreneur in Hollywood Risky Business 1983

Directed by Paul Brickman, Risky Business is a 1983 romantic comedy film starring Tom Cruise and Rebecca De Mornay in the lead roles. The film tells the story of a high-achieving high school student Joel Goodson, who tries to have some fun when his parents are away leaving the house to himself.

However, the fun turns into chaos and Joel must try and get things in order before his parents return. The way he does it is what forms the rest of the story.

Something Ventured (2011)

Something Ventured 2011 netflix movie documentary

A 2011 documentary film, Something Ventured is directed by Daniel Geller and Dayna Goldfine. The film focuses on the beginning of American venture capitalism in the mid-20th century and contains interviews of famous venture capitalists and entrepreneurs of the 60s, 70s, and the 80s.

Moneyball (2011)

Moneyball starring brad pitt about business

Moneyball is another sports drama film on our list of best Hollywood films for Entrepreneurs after Jerry Maguire. Instead of American Football, Moneyball focuses on Baseball and features the nonfiction story of the 2002 season of Oakland Athletics Baseball team and the role of their general manager Billy Beane, played by Brad Pitt, to form a competitive team for the season. Directed by Bennett Miller, the film is adapted from the nonfiction book of the same name authored by Michael Lewis.

Lord of War (2005) 

movies for entrepreneur lord of the war 2005 nicholas cage

Lord of War is a war crime film directed by Andrew Niccol. The film features the stories of real-life arms dealers and smugglers in a fictional story and tells the story of an illegal arms dealer played by Nicolas Cage. Well, the film is not a great example for a dream career, but there are some traits of Nicolas Cage’s character that can be used as lessons for budding entrepreneurs.

The film talks about finding business opportunities and turning the odds into one’s favor. However, I advise you to keep the illegal activities out of the mind while you are learning these traits from the movie.

The Social Network (2010)

The social network biopic of Mark zuckerburg

The Social Network is a Hollywood biographical drama film about the founding and struggles dealt by Facebook and its founder Mark Zuckerberg in the early days.

The story of the film was adapted from the book The Accidental Billionaires: The Founding of Facebook, A Tale of Sex, Money, Genius, and Betrayal written by Ben Mezrich in 2009.

Rogue Trader (1999)

Rogue Trader 1999 film

Rogue Trader is a 1999 biographical drama film directed by James Dearden based on the life of former derivatives broker Nick Leeson and features the 1995 collapse of Barings Bank.

The film was adapted from the book titled Rogue Trader: How I Brought Down Barings Bank and Shook the Financial World written by Leeson himself. The film stars Ewan McGregor as Leeson and Anna Friel as his wife Lisa.

The Devil Wears Prada (2006)

The Devil Wears Prada film about business

Directed by David Frankel, The Devil Wears Prada is a comedy-drama film that features the fashion industry. Starring Meryl Streep and Anne Hathaway in the lead roles, the film is adapted from the novel of the same name authored by Lauren Weisberger in 2003. The film focuses on the hardships and challenges of the fashion and media industry.

Glengarry Glen Ross (1992)

Glengarry Glen Ross 1992 film about entrepreneur

Based on a popular theatrical play of the same name, Glengarry Glen Ross is a 1992 drama film directed by James Foley. The film tells the story of two days and features the life of four real estate salesmen, all of whose lives are changed when they realize that the corporate office has sent a trainer and only the top two of the four salesmen will continue at the firm after a week. The film stars Al Pacino, Jack Lemmon, Alan Arkin, and Ed Harris as the salesmen, whereas Alec Baldwin plays Blake, who plays the trainer.

The Founder (2016)

The Founder movie about mcdonalds real life story

The Founder is a Hollywood film based on Real life of businessman Ray Kroc and tells the story of the rise of America’s favorite fast-food chain, McDonald’s. Directed by John Lee Hancock, the film stars Michael Keaton as Ray Kroc, whereas Nick Offerman and John Carroll Lynch are the co-stars as McDonald’s founders Richard and Maurice McDonald.

Over to you!

That’s our list of inspiring and motivational Hollywood movies for entrepreneurs. What’s yours?

Let us know in the comments below.