Hollywood has long been fascinated by larger-than-life business personae, as Matthew Pejkovic has documented in this series portrayals of business in cinema. Here he is, once again, to “Show us the movies!!!” — with a look at more business films relevant to the present day.

Jerry Maguire (1996)

By the mid 1990s, American sports had become a billion-dollar industry. Figures such as Michael Jordan and Mike Tyson transcended their professions and became global superstars, earning millions in endorsements.

Jerry Maguire delved behind the scenes and looked at the business side of sports. Tom Cruise starred as the title character, a sports agent whose radical idea of taking on less clients, asking for less money and focusing on developing relationships with the clientele, has him fired from his prestigious position in one of the premiere sports firms in the country.

Starting anew with a devoted employee by his side (Renee Zellweger) and with one client willing to stick by him, an egotistical football player named Rod Tillman (Cuba Gooding, Jr.) Jerry goes through the usual struggles of starting a new business: How will the bills be paid? Who will take care of medical costs and other expenses? How will he market himself?

Writer/director Cameron Crowe (Almost Famous) took inspiration from real-life agent Leigh Steinberg, who in his 35-year career represented hundreds of professional athletes from all sports.

His insistence that his clients sign contracts with clauses that require they give back to their communities left an impression on Crowe, who wanted to write a story about values, ethics, relationships and entrepreneurship in the sports industry.

“It’s fashionable now, after the movie, for a lot of agents to talk about heart,” said Crowe. “But Leigh was the only one talking like that in 1993, when I began research.”

“Show me the money!” and “You complete me” became catch phrases for a new generation, and Jerry Maguire became a hit both critically and financially.

“Cameron was able to get an inside look at professional football from the standpoint of athletes and agents and general managers that few people have ever seen,” said Steinberg. “He probably has a fresher take and a truer insight into how our world really works than anybody from his business has ever seen. How much of that real life shows up on the screen only he could judge.”

Jerry Maguire Trailer

Matthew Pejkovic is a freelance film journalist located in Sydney. He writes for various print and online publications including FilmInk and The Retiree. He also runs his own website, Matt’s Movie Reviews.net and you can follow him on Twitter via @mpejko.