Money at the Movies

From Wall Street trading floors and corporate boardrooms to baseball front offices and fast-food empires, Hollywood has spent decades turning business, finance and the pursuit of wealth into big-screen entertainment. Sometimes the lesson is about smart strategy. Sometimes it’s about greed. And sometimes the lesson is simply: please do not try this at home.

As the weather cools and movie nights start sounding a little more appealing, here are a few finance and business movies worth adding to your watchlist.

Wall Street (1987)

It’s hard to make a list like this without starting here. Wall Street introduced audiences to Gordon Gekko and his infamous “greed is good” philosophy while following an ambitious young stockbroker eager to make his mark.

The money lesson: If an investment opportunity requires insider information and a complete disregard for ethics, perhaps reconsider.

Watch it for: Peak 1980s excess, suspenders, slicked-back hair and one of the most famous fictional financiers ever created.

The Wolf of Wall Street (2013)

Leonardo DiCaprio stars as Jordan Belfort in this over-the-top story based on Belfort’s rise and fall in the brokerage world. It’s outrageous, excessive and definitely not an instructional video for running a financial services firm.

The money lesson: Rapid growth and enormous revenue don’t mean much when the business underneath them isn’t ethical…or legal.

Watch it for: A reminder that strong internal controls are probably a good thing.

The Big Short (2015)

How do you make mortgage-backed securities and the 2008 financial crisis entertaining? Apparently, you cast Christian Bale, Steve Carell, Ryan Gosling and Brad Pitt.

The Big Short follows several investors who recognized problems in the U.S. housing market before the financial crisis and bet against it. Along the way, the movie uses some unconventional methods to explain complicated financial concepts.

The money lesson: Understand what you’re investing in. If no one can clearly explain how something makes money, asking more questions is usually worthwhile.

Watch it for: Possibly the most entertaining explanation of complex financial instruments ever put on film.

Moneyball (2011)

Finance doesn’t have to mean Wall Street. Moneyball tells the story of Oakland A’s general manager Billy Beane and his effort to build a competitive baseball team with a limited budget by using data and analytics differently than his competitors.

The money lesson: More resources don’t always equal better results. Good data can help businesses identify opportunities others overlook and make smarter decisions about where to invest.

Watch it for: Brad Pitt, baseball and a surprisingly compelling case for using KPIs.

The Social Network (2010)

Part technology story, part business story and part cautionary tale about mixing friendships with ownership interests, The Social Network dramatizes the early days of Facebook and the disputes surrounding its creation.

The money lesson: When you’re starting a business with other people, agreements, ownership percentages and documentation matter. A lot.

Watch it for: A reminder that your CPA and attorney may not be the most exciting people at the table, but you probably want them there.

The Founder (2016)

The Founder tells the story of Ray Kroc and the transformation of McDonald’s from a small restaurant operation into a massive franchise business.

One of the movie’s most interesting business lessons actually isn’t about hamburgers at all. It’s about real estate and the business model behind the restaurants.

The money lesson: Sometimes the most valuable part of a business isn’t the most obvious one. Understanding what actually drives profitability can completely change a company’s strategy.

Watch it for: A fascinating look at scaling a business and some complicated questions about ambition, partnerships and business ethics.

Trading Places (1983)

For something considerably lighter, Trading Places puts Eddie Murphy and Dan Aykroyd at the center of a bet between two wealthy commodities brokers.

There are commodities markets, financial schemes and an elaborate orange juice futures plot. What more could an accounting newsletter ask for?

The money lesson: Markets can be unpredictable, information is valuable and betting your fortune on frozen concentrated orange juice may not be a diversified investment strategy.

Watch it for: Pure 1980s comedy with a financial twist.

Margin Call (2011)

If The Big Short shows the financial crisis from the perspective of people who saw it coming from outside, Margin Call takes viewers inside a fictional investment bank as employees realize their firm has a very serious problem.

The movie unfolds largely over a single night as executives try to determine what to do next.

The money lesson: Risk management matters long before a crisis arrives. By the time everyone is gathered around a conference table at 2 a.m., your options may already be limited.

Watch it for: Less Hollywood excess, more boardroom tension.

And the Award Goes To…

Whether you’re interested in investing, entrepreneurship, economics or simply watching people make spectacularly questionable financial decisions, there’s a money movie for you.

And while Hollywood tends to make finance a little more dramatic than the average day at the office, many of these movies share a surprisingly practical message: know your numbers, understand your risks, surround yourself with good advisors and don’t let short-term opportunities distract you from the bigger picture.

Admittedly, that may not make for the most exciting movie plot. But it’s generally a much better business strategy.