Top 10 Movies About Business Executives and Entrepreneurs Released from 2000-2010

We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 entrepreneur and business movies from 2000-2010. Don’t forget to check out other lists throughout Thought for Your Penny.

10. The Pursuit of Happyness (2006) 67% at Rotten Tomatoes

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With all the MLM schemes driving people into poverty, this story of a salesman who will do anything to provide for his son is touching. By the time you’re done watching, you’ll be inspired to solve a Rubik’s cube at a bare minimum. With any luck, it’ll motivate you to sell more than Boiler Room ever did.

Rating: PG-13
Director: Gabriele Muccino
Starring: Will Smith, Thandie Newton, Jaden Smith

9. Lord of War (2005) 61% at Rotten Tomatoes

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An arms dealer provides a glimpse into the real-life business of war while on the run from the law. People get guns on both sides of every conflict, and we don’t like to think about how. It’s a profitable business, though, so you know it’s happening every day.

Rating: R
Director: Andrew Niccol
Starring: Nicolas Cage, Ethan Hawke, Jared Leto

8. Up in the Air (2009) 91% at Rotten Tomatoes

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The image of the traveling businessman used to be so glamorous pre-9/11. Ryan Bingham makes it look like a dream life again, until he finds himself on the chopping block he directs. Clooney and Kendrick add the right amount of charm to this popcorn flick.

Rating: R
Director: Jason Reitman
Starring: George Clooney, Vera Farmiga, Anna Kendrick

7. Blood Diamond (2006) 62% at Rotten Tomatoes

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Ever wonder where that diamond on your finger or neck came from? Blood Diamond tells the story of a fisherman, smuggler, and business syndicate racing for possession of a large, rare diamond that is priceless on the gem market.

Rating: R
Director: Edward Zwick
Starring: Leonardo DiCaprio, Djimon Hounsou, Jennifer Connelly

6. Thank You for Smoking (2005) 86% at Rotten Tomatoes

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Nick Naylor is a lobbyist who believes in the tobacco industry so much, he can get anyone else to. Of course, this is difficult when remaining a role model to your family. He rides the line well, though, providing a glimpse into a world none of us wants to admit exists in every industry.

Rating: R
Director: Jason Reitman
Starring: Aaron Eckhart, Maria Bello, Cameron Bright

5. The Company Men (2010) 67% at Rotten Tomatoes

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Three men who trusted their lives with corporate America are suddenly put through the ringer with a round of layoffs. Corporate downsizing is an untold secret of the business world, and The Company Men shines a light on the lives it affects.

Rating: R
Director: John Wells
Starring: Ben Affleck, Tommy Lee Jones, Chris Cooper

4. The Social Network (2010) 96% at Rotten Tomatoes

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Mark Zuckerberg created one of the most prolific social networks of all time. The Social Network documents the meteoric rise of Facebook from a college dorm into one of the world’s biggest businesses. It’s a bit dramatized, but still covers the important points.

Rating: PG-13
Director: David Fincher
Starring: Jesse Eisenberg, Justin Timberlake, Andrew Garfield

3. The Devil Wears Prada (2006) 75% at Rotten Tomatoes

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When Andy Sachs gets a job with Miranda Priestly, the hard-nosed editor-in-chief of a prestigious fashion magazine, she’s excited. That is, until she’s put through the ringer and the demanding work gets in the way of her personal life.

Rating: PG-13
Director: David Frankel
Starring: Anne Hathaway, Meryl Streep, Adrian Grenier

2. Inside Job (2010) 98% at Rotten Tomatoes

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The 2008 financial meltdown affected everyone, but we still don’t have answers as to how and why it happened. Damon narrates the facts leading to this scary economic situation, although it does nothing to stop it from continuing.

Rating: PG-13
Director: Charles Ferguson
Starring: Matt Damon, Gylfi Zoega, Andri Snaer Magnason

1. Enron: The Smartest Guys in the Room (2005) 97% at Rotten Tomatoes

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Enron is one of the biggest financial disasters in American history. See the rise and fall  of this business through the eyes of documentarian Gibney. Faulty business practices, bad accounting, and greed destroy a large business that never should have been.

Rating: NR
Director: Alex Gibney
Starring: John Beard, Tim Belden, Barbara Boxer


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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