Top 10 Horrible Movie Bosses

Top 10 Horrible Movie Bosses

The FilmGuruThis week, Horrible Bosses comes to theaters. Movies about the workplace are as old as the art of cinema. And while we usually go to the movies to escape the real world, sometimes reality can’t help but leak through. We often see characters we recognize, and that even includes bosses.

In Horrible Bosses, Nick Hendricks (Jason Bateman), Dale Arbus (Charlie Day) and Kurt Buckman (Jason Sudeikis) have had it with their bosses. But what can you do when your boss is a psycho, a man-eater, or a total tool? Quitting is not an option. So, the guys devise a convoluted but foolproof plan to rid the world of their respective employers… permanently.

We’re not recommending that our readers end bad workplace relationships so drastically. The truth is, no matter how bad your boss is, it could be worse.

We wouldn’t wish these bosses on anyone. These are the baddest of the bad. So the next time your boss is hounding you about missed deadlines or asking you to help him download Angry Birds on his iPhone, remember that it could be worse. You could have one of these cinematic horrible VIPs.

Bad Bosses - Tony Stark10. Tony Stark from Iron Man (2008)

Not only is Tony Stark (Robert Downey, Jr.) one of the most egotistical bosses around, he’s also horribly dependent on his personal assistant, Pepper Potts (Gwyneth Paltrow). She has to organize his schedule, make excuses for him, and call the contractor every time he blows up his workshop. And every now and then she has to install his personal arc reactor to keep his heart beating.

Bad Bosses - Bill Lumbergh9. Bill Lumbergh from Office Space (1999)

He may not be a horrible boss, but Bill Lumbergh (Gary Cole) is definitely one of the most annoying. He’s not content to send out a memo about the cover sheet on the TPS report, he pops up to make sure everyone has read it. And then there’s his annoying habit of telling (not asking) Peter Gibbons (Ron Livingston) that he needs to come in to work on Saturday.

Bad Bosses - John Ammer8. John Ammer from Click (2006)

Everyone has a bad boss now and then, but John Ammer (David Hasslehoff) is a perfect example of how bad a boss can be. He’s overbearing, and he makes Michael (Adam Sandler) miss a lot of important family time. Ammer is slimy, smug, and demeaning to women. Personally, I think Michael was too easy on Ammer when he farted in the boss’s face.

Bad Bosses - Daniel Cleaver7. Daniel Cleaver from Bridget Jones’s Diary (2001)

Sexual harassment is always frowned upon in the workplace, but Daniel Cleaver (Hugh Grant) apparently never got the memo. Despite the fact that he’s a notorious womanizer, Bridget (Renée Zellweger) starts flirting with him over e-mail and — against her better judgment — begins dating him. But things turn out badly when he proves what a lascivious man he is.

Bad Bosses - Blake6. Blake from Glengarry Glen Ross (1992)

No one likes to find out their job is in jeopardy. But the situation can be handled with a bit of decorum… or you can send Blake (Alec Baldwin) to do the job. This vulgar, arrogant man is sent by the owners of the real estate office to motivate the salesmen. Instead, he screams and curses at the salesmen, before announcing only the top two sellers will stay and the rest of them will be fired.

Bad Bosses - Frank Hart5. Franklin M. Hart Jr. from Nine to Five (1980)

You may think he was a product of his time, but Frank (Dabney Coleman) was a sleazy and chauvinistic boss — even for the ’70s. He repeatedly tries to seduce his secretary (Dolly Parton), then passes over Violet (Lily Tomlin) for a promotion. It’s little surprise that the two of them, along with the new hire, Judy (Jane Fonda), plot their revenge on him.

Bad Bosses - Katharine Parker4. Katharine Parker from Working Girl (1988)

Katharine Parker (Sigourney Weaver) is a new financial executive at Petty Marsh. She seems nice and supportive, but when she steals the ideas Tess (Melanie Griffith) shares with her, it’s clear that she’ll do anything to stay at the top. When Tess protests, Katharine gets her fired. It takes a special kind of bad boss to steal someone’s work and then denounce them as “just a secretary.”

Bad Bosses - Gordon Gekko3. Gordon Gekko from Wall Street (1987)

The ’80s brought a new level of bad to business. And no one embodies that badness better than Gordon Gekko (Michael Douglas). As he spouts the right-wing economic philosophy “Greed is Good,” he uses the moral flexibility of an up-and-coming trader, Bud Fox (Charlie Sheen), to get insider information. Gekko’s manipulation nearly destroys Fox, just another casualty in his career.

Bad Bosses - The Emperor2. The Emperor from Return of the Jedi (1983)

So, your boss is a galactic-class jerk. But you’ve never had a boss as bad as the one Darth Vader answers to. After his last big project blew up, it took a lot of work to rebuild. And now the Emperor (Ian McDiarmid) isn’t satisfied with crushing the rebellion. He also wants to turn Darth’s son to the Dark Side, and if that doesn’t work he’ll kill young Skywalker. You think your boss is demanding…?

Bad Bosses - John Milton1. John Milton from The Devil’s Advocate (1997)

Some bosses seem like evil incarnite. And then there’s John Milton (Al Pacino). After Florida defense attorney Kevin Lomax (Keanu Reeves) wins a big case, Milton offers him a place at his New York law firm. But Milton is interested in Kevin for other reasons. For starters, the young man is his son. Oh… and Milton is really the devil. To top the list, Milton wants Kevin to conceive a child with his half-sister so she can give birth to the Antichrist. Seriously. Worst. Boss. Ever.

So, what do you think? Did we find all the horrible movie bosses? If you have a cinematic boss in mind who should be on this list, leave a comment below and let us know!


5 Comments on Top 10 Horrible Movie Bosses


  1. I was just thrilled to see I wasn’t on the list.


  2. Rodney, yeah we included Lumbergh (see #9). Bob, I never thought of old Scrooge. He’s definitely one of the worst bosses, even if his origins are in literature.


    • Damn, I missed it. I was looking right at it too.


  3. This is a good list — would Scrooge be eligible?


  4. What about Bill Lumbergh from Office Space. Gary Cole’s awesome in that role…. what a douche!

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