Top 10 Movies About Business Executives and Entrepreneurs Released from 1990-2000

We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 movies about the business world from 1990-2000. Don’t forget to check out other lists throughout Thought for Your Penny.

10. Glengarry Glen Ross (1992) 94% at Rotten Tomatoes

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Real estate and sales are the targets of this movie, filmed in a pre-crash economy. Coupled with Inside Job and The Big Short, it serves as a primer to mortgage greed. There is no one villain – it’s systematic failure. Also it has a motto you’re certainly tired of hearing if you’ve ever worked sales.

Rating: R
Director: James Foley
Starring: Al Pacino, Jack Lemmon, Alec Baldwin

9. Office Space (1999) 79% at Rotten Tomatoes

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If you’ve ever worked in an office, The Office TV show is a decent portrayal. Judge’s Office Space, however, really lampoons the ridiculousness of cubicle life. Doesn’t resonate the same since I started freelancing, but maybe that’s just me.

Rating: R
Director: Mike Judge
Starring: Ron Livingston, Jennifer Aniston, Stephen Root

8. Pirates of Silicon Valley (1999) 90% at Rotten Tomatoes

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There’s yet to be a decent movie about Steve Jobs released in theaters, but this made-for-TV movie is an entertaining look at both he and Bill Gates’ climbs up the ladder to create Apple and Microsoft. It’s much-see TV in today’s technological world.

Rating: NR
Director: Martyn Burke
Starring: Anthony Michael Hall, Noah Wyle, Joey Slotnick

7. The Family Man (2000) 53% at Rotten Tomatoes

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We all have choices to make – either dedicate most our time to our family or our careers. This movie explores the life-changing differences that occur when you choose one or the other.

Rating: PG-13
Director: Brett Ratner
Starring: Nicolas Cage, Tea Leoni, Don Cheadle

6. Boiler Room (2000) 67% at Rotten Tomatoes

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The original Wolf of Wall Street, Boiler Room follows the same story from a slightly different perspective. Instead of Leonardo DiCaprio, we’re given Diesel, who channels Riddick and Toretto into a suit-and-tie-wearing stock broker specializing in penny stocks. When I worked at Best Buy, our supervisor watched this movie every night and quoted it to us every morning.

Rating: R
Director: Ben Younger
Starring: Giovanni Ribisi, Vin Diesel, Nia Long

5. Jerry Maguire (1996) 83% at Rotten Tomatoes

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Jumping from corporate America to freelancing is scary and difficult. Hot shot sports agents Jerry Maguire pulls it off in one of the best quitting scenes in Hollywood. Check out Half Baked for the king of quits.

Rating: R
Director: Cameron Crowe
Starring: Tom Cruise, Cuba Gooding Jr., Renee Zellweger

4. Other People’s Money (1991) 33% at Rotten Tomatoes

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When a corporate raider threatens a hostile takeover of a mom and pop shop, they hire a lawyer he falls in love with. In the wake of Hollywood’s #MeToo scandal, this reminds us that sexuality has long been part of corporate America.

Rating: R
Director: Norman Jewison
Starring: Danny DeVito, Gregory Peck, Penelope Ann Miller

3. The Insider (1999) 96% at Rotten Tomatoes

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The Insider gives us a lot of necessary information about business. We see the corruption of Big Tobacco, the plight of the whistleblower, and the corruption of media. On top of that, it’s all based on real-life events.

Rating: R
Director: Michael Mann
Starring: Russell Crowe, Al Pacino, Christopher Plummer

2. Barbarians at the Gate (1993) 67% at Rotten Tomatoes

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Another movie based on a true story (and another one made for TV), this one follows the buyout of RJR Nabisco. In case you weren’t aware, tobacco company R.J. Reynolds and food company Nabisco were once one in the same. As a matter of fact, take some time now to familiarize yourself with subsidiaries, because they’re super important in today’s world.

Rating: R
Director: Glenn Jordan
Starring: James Garner, Jonathan Pryce, Peter Riegert

1. The Hudsucker Proxy (1994) 56% at Rotten Tomatoes

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After the CEO of Hudsucker Industries commits suicide, they appoint a moron in his place, hoping to buy the company out for pennies on the dollar (see bidding war in above film for reasoning). Instead, Norville Barnes comes up with the hula hoop and strengthens the brand more than ever as an investigative reporter is hot on the trail of the scheme.

Rating: PG
Director: Ethan Coen, Joel Coen
Starring: Tim Robbins, Jennifer Jason Leigh, Paul Newman

 

Versability

Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer.

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