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Today is National Boss’ Day, So Here’s The Top 5 Worst Pop Culture Ones I Can Think Of

By Kate Hudson | Miscellaneous | October 16, 2018 |

By Kate Hudson | Miscellaneous | October 16, 2018 |


Every day is a national holiday for something, and today is no exception. Today is Boss’ Day! So if you work in an office, you were most likely forced to chip in on something for your boss you’d never pick out yourself, or you completely forgot and are scrambling to send a late-night I-bet-you-think-I-forgot-but-this-was-always-the-plan-to-tell-you-later email this very moment. Either way, it’s a great way to be forced into recognizing someone who runs your life and gets paid to do it.

In honor of this, I’ve compiled by no means a comprehensive list of the top 5 worst bosses I can think of.

Willy Wonka


Let’s ignore the fact that he’s just creepy, and keeps a psychedelic tunnel of chocolate water in his factory, for reasons known only to him—let’s focus on his treatment of the Oompa Loompas. I see no protective safety gear in their day to day operations. They are always on the ready, so I can’t imagine they’re having regular breaks to get them off their feet. Willy Wonka was erratic and prone to fits of anger at his guests—what’s going on behind closed doors with the Oompa Loompas when he doesn’t have guests around?!



Murder. Mayhem. Mischief. These are all things that are openly encouraged in Sauron’s employ. Not to mention the fact that his army of orcs is clearly not a volunteer one, and most were more than likely conscripted in by force. Sauron wants his army to be hungry and mean, and as a result, doesn’t treat them very nicely. Now, I’m not saying the orcs aren’t bloodthirsty by nature, but I am saying that like with all things, an organization leads from the top down. If Sauron is encouraging all things brutal, it doesn’t sound like a particularly welcoming work environment, does it?

Darth Vader


Dudes, he tried to suffocate a colleague for simply disagreeing with him! He murdered multiple subordinates because they (accidentally) let the Rebels get away! There is literally no part of working for Darth Vader that should appeal to anyone in the slightest. Sure, he’s the bad guy and yes, he will only stop at complete galactic domination, but does he have to be so mean while doing it? He terrifies everyone, and that’s simply not conducive to a healthy workplace environment.

Ursula, The Sea Witch


Poor unfortunate souls (to have to work with Ursula) indeed. Look, she creates bad faith contracts that she has no intention of fulfilling, and actively works against any contractor in her employ to sabotage them. She also ends up getting her right-hand hires killed in a showdown against a more powerful mer-kin. Working for her seems exhausting, and more importantly, deadly.

Dustin Rowles


(Actual footage of Dustin, taken in the last Overlord Video Conference, when he made us watch his latest spoken word performance, which lasted over an hour, in total silence. I had just asked him if he was almost done…)

I don’t know what to say, other than that we had a good run. Today will be my last article for Pajiba, because I simply cannot take Dustin’s micromanaging, excessive expository ramblings on the latest episode of Suits (usually with diagrams) or general bad attitude anymore. As readers of Pajiba, you *think* you know Dustin, but did you know that in order to write for the site, you have to spend an hour a week filling out sweepstake entries in Dustin’s underage children’s name (for tax reasons, he says) and you don’t get to keep any of the winnings? Did you know you have to put up with many late-night rambling phone calls about Law & Order re-runs that have been in syndication of upwards of 20 years and yet still send him into a blind rage?! No, neither did I, until I came on board. It’s simply too much—and I can’t take it anymore. So I quit. I’ll see you all in the funny pages (…or most likely tomorrow, because I kind of need the job; I have a bit of a sweepstakes addiction myself…)

We had a good run. Share your horrible (or good, I’m not picky) boss stories in the comments.

Kate is a staff contributor. You can follow her on Twitter.

Header Image Source: Lucasfilm Ltd.

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