The movie industry has long been fascinated by entrepreneurism, going back to the days of black and white films.
Since the big screen is always larger than life, most entrepreneurial depictions are exaggerated, melodramatic and sometimes downright implausible. They are, however, almost always entertaining and shed some interesting light on how we as a society view entrepreneurial archetypes.
Some of these films are biopics, telling the story of a real-life individual (such as “The Social Network” about Mark Zuckerberg).” Others are entirely fictional, like the eponymous “Jerry Maguire.” While they run the gamut from comedy to tragedy, needless to say, they can all be fairly described as character studies.
Probably the first great entrepreneurial film, and still among the best of all time, is the Orson Welles masterpiece “Citizen Kane.” Loosely based on the life of newspaper magnate William Randolph Hearst (who banned mention of it in his publications), it was groundbreaking in its storytelling techniques and cinematography. It is both a classic and very twisted rags-to-riches story, and its central character, though not entirely unsympathetic, ultimately becomes more anti-hero than hero. Though dated by its 1941 release date, it remains one of the greatest-ever American films.
Another larger-than-life figure in American enterprise gets a more straight-on portrayal in “The Aviator,” the story of Howard Hughes. The movie mostly covers a 20-year span of Hughes’ life, during which he became an aviation pioneer. One could argue that “The Aviator” focuses too much on his increasing mental instability at the expense of his contributions to flight technology, but it is an epic and very well-made film.
On the more lighthearted side, “Jerry Maguire” is a fun, fictional and somewhat farcical look at the world of sports agents. Its David vs. Goliath, good guys can finish first story makes it a feel-good viewing experience. And of course, the catch phrase “Show me the money!” became part of the American lexicon.
Women as entrepreneurs have been given the spotlight in a variety of films. One uplifting option is the biopic “Joy,” an account of the life of inventor and entrepreneur Joy Mangano. “The Intern” is a well-made look at the complexities women face in balancing life and career, and after quite a few twists and turns, reaches a rewarding conclusion.
For some reason, movies about small businesses seem to tend more toward the comedic. Examples would be “Barbershop,” which nicely depicts the importance of smaller establishments to the communities they serve; and “Kinky Boots” (based on a true story), which is a very entertaining look at how a small operator often must find unusual and creative approaches to compete with larger enterprises. Another flick, “High Fidelity,” explores the joys and challenges of turning one’s passion into a business.
In the more straightforward biopic category, “The Founder” tells the story of McDonald’s founder Ray Kroc and the relentless determination he needed to sell his “billions and billions” of hamburgers. At the opposite end of the business spectrum, “Steve Jobs” realistically recounts the downs as well as the ups of one of the most successful tech magnates.
What’s to be learned from watching Hollywood’s entrepreneurs? The best of these films, like all good movies, offer thoughtful insights into human nature. More specifically, they examine our transactional society, our collective priorities and the frequent compromises that are made in pursuit of business success.
Viewing them as career and business models, however, might be pushing it ….
Real-life entrepreneurs are incredibly busy people who struggle to find any spare time. But everyone needs a break now and then, so why not go catch a good entrepreneurial flick?
Keith Twitchell spent 16 years running his own business before becoming president of the Committee for a Better New Orleans. He has observed, supported and participated in entrepreneurial ventures at the street, neighborhood, nonprofit, micro- and macro-business levels.

