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What Entrepreneurs Can Learn From These 6 Movies With Horrible Bosses Learn how to be a leader by watching what not to do.

By Deep Patel Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.

Columbia Pictures

Most people can relate to having had a bad boss. They are, unfortunately, pervasive in the workplace. But getting to watch a bad boss as part of a movie — that can be kind of fun! Especially because big-screen bad bosses usually get what's coming to them.

Maybe people enjoy watching bad bosses on the big screen because they can relate to the disgruntled, underdog employee who has to grapple with the heavy-handed tyranny of a toxic leader. Or maybe they're secretly rooting for the jerk of a boss, because, for all their faults and blunders, they do have some redeeming factors.

In the end, maybe it's just that obnoxious and mean-spirited bosses make for great movies. Here are six of the worst big-screen bosses that you love to hate, and the lessons we can all learn from their mistakes.

1. Office Space

Office Space's Bill Lumbergh is the archetypal idiot boss that you love to hate. In fact, he's such a bad boss that "cool bosses" do impressions of him in an attempt at self-deprecating humor: "Mmmm…yeeeaaaahhh, we're gonna need…" Office Space's plot is one of the finest satires of everyday life in the cubicle jungle that makes up so much of corporate America.

Pete Gibbons is an unmotivated programmer who is trapped in a monotonous, soul-crushing office job filled with menial, mindless and largely irrelevant tasks. The movie is both hilarious and incredibly insightful, and has held up well in the decades since it first graced movie theaters.

Lessons learned: Stop micromanaging! Good bosses energize their work environment and motivate those who work for them. If there's one mantra the movie repeats, it's how the moronic actions of a controlling boss can suck the life out of a company.

Business culture is created from the top down. Be respectful of your employees and stop infringing on their off time. If you want to motivate someone, find out what their "red stapler" is. This is their heart's desire, and if you can figure this out, you'll know how to tap into their internal motivation.

2. The Devil Wears Prada

In the world of fashion, Miranda Priestly is the quintessential mean girl and the character who gives the movie The Devil Wears Prada its name. The plot centers around Andy, a fresh-out-of-college graduate and aspiring journalist who lands a job that "millions of girls would kill for" with Runway magazine, of which Miranda is editor in chief.

Andy initially fumbles and bumbles through her job as she contends with Miranda, who is downright abusive of her staff. Andy slowly begins to find her way, learning how to handle uncomfortable situations, rise to the challenge and navigate unfamiliar worlds. We see how hard work eventually pays off.

Lessons learned: From Miranda, we learn that exerting fear over your underlings isn't a good strategy in the long run. Eventually, your best and brightest employees are going to get sick of your threatening behavior and are going to flee to better jobs. Also, don't be unnecessarily vague. Give employees the key they need to be successful by providing them with the information they require to do their job well.

3. The Social Network

Most of us are already familiar with the basics of this plot: Mark Zuckerberg is a student at Harvard University when he creates a campus website called Facemash by hacking into the college database. After being hired by two upperclassmen for a different project, he comes up with the concept for Facebook (which he initially called Thefacebook). Eventually, Zuckerberg's vision pans out, but not before he is sued and ends up backstabbing some of his friends.

Lessons learned: It's not always about who has the idea to begin with, but who can best execute it. In the end, Zuckerberg is the one who got Facebook launched. No one else had the skill to make that happen. He was successful because he figured out how to be of service. He followed his idea through, believing revenue would follow (and he was right).

But the movie also depicts Zuckerberg as an arrogant, paranoid jerk who screwed over his friends to climb the ladder to success. (Bear in mind that Zuckerberg himself wasn't a big fan of how he was portrayed.)

While self-confidence is key to carrying you through the rough spots, being overly arrogant is going to cost you money and friends. Have confidence in your abilities, but check your arrogance at the door.

4. 9 to 5

In this classic comedy, three female office coworkers (Judy Bernly, Doralee Rhodes and Violet Newstead) seek revenge on their class-A chauvinist boss, Franklin Hart, Jr., who mistreats his female subordinates.

The three women eventually take matters into their own hands and kidnap Hart. As you might expect, in the end, everyone gets their just deserts. This film depicts one of the worst types of bosses out there: one who completely lacks integrity and is out to manipulate everyone around them to his own benefit.

Lessons learned: Obviously, the biggest lesson from this movie is not to be a "sexist, egotistical, lying, hypocritical bigot" (in the immortal words of Judy Bernly). Furthermore, it's important to have some self-awareness of what you're doing. Creating a toxic environment is going to result in reduced productivity, higher turnover and lack of loyalty.

Unfortunately, Hart is never fired for his actions, but during his absence from work, the trio showed they were much more efficient at running the office on their own. A word to the wise: Sometimes you have to know when to get out of your own way.

5. The Devil's Advocate

It's easy to say your boss is the devil, but what do you do if your boss is actually Satan himself? In The Devil's Advocate, the devil (who goes by the name John Milton) lures Kevin Lomax, a morally flexible defense attorney, into a job with a big New York firm, which of course comes with a hefty salary and a fancy Manhattan apartment. As the plot unfolds, the ever-charismatic and persuasive Milton pulls Lomax deeper into his snare.

Lomax, who was once driven by a desire for professional excellence, becomes ruthless and cutthroat. But Milton doesn't have to twist Lomax's arm to do bad things. In fact, Milton tells Lomax upfront all the horrible things his choices might lead to.

Lessons learned: Stay true to your inner compass. Clearly define who you are and what you stand for, and don't ever let anyone or any amount of money change that. Also, no matter how successful you get, a little humility will keep you grounded.

6. Avengers: Infinity War and Endgame

As far as boss villains go, it's hard to beat Thanos. After all, he literally killed half of all living creatures in all known universes. That's a cruel and merciless move that's bound to get you labeled a callous megalomaniac. Let's face it: Being the ultimate villain and the architect of every world's calamity is going to earn you a bad rap as a really bad boss. Also, all the worlds' superheroes are going to become obsessed with taking you down in epic fashion.

Lessons learned: Bosses who are tyrannical monsters will ultimately discover that all the power in the world doesn't amount to squat once enough people (superhero or not) are motivated to tear you down. But there are also a few key good things we can take away from his leadership style.

Thanos has a laser-like focus on his goal and never deviates from that clearly stated mission. He is equally just (or unjust) to everyone. He's always prepared to meet the competition in a head-to-head battle. And he is never lacking in self-confidence, though he probably should have checked his arrogance, as this ends up getting him killed twice over.

Deep Patel

Entrepreneur Leadership Network® Contributor

Serial Entrepreneur

Deep Patel is a serial entrepreneur, investor and marketer. Patel founded Blu Atlas, the fastest-growing men’s personal care brand, and sold it for eight figures in 2023, less than 18 months after its launch.

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