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Top 10 Worst Fictional Bosses

I have come up with a list of who I think are the top 10 worst fictional bosses. The order is descending from 10 to the #1 worst fictional boss.

10. Ari Gold, Entourage

As Vincent Chase’s ruthless and smarmy agent in “Entourage,” Ari is a savvy businessman who keeps his clients happy (for the most part), and his employees miserable.

9. Tony Soprano, The Sopranos

Tony has his own way of getting things done while keeping the northern New Jersey’s most powerful criminal organization functioning properly and keeping dissonance to a minimum. He has committed at least eight murders in the show, (maybe more in his lengthy career in the Mafia). As a Boss, he is also fully responsible for the deaths of others killed on his orders.

8. Dr. Gregory House, House

House’s character frequently shows his cunning and biting wit, enjoys picking people apart – especially his employees, and often mocks their weaknesses.

7. Gordon Gekko, Wall Street

His credo, “Greed is good,” went on to inspire the Wall Street we have today and the worldwide economic collapse that followed. The problem with Gekko is that he’s one of those bosses who makes doing bad things seem like so much damn fun!

6. Miranda Priestly, The Devil Wears Prada

Miranda is everything we don’t look for in a boss. Pushy, arrogant, demanding, belittling, high strung. And, worst of all, she surrounds herself with “Yes Men” who only bolster her false sense of brilliance and self-righteousness.

5. Les Grossman, Tropic Thunder

Grossman is that rare breed of boss that is absolutely, batshit crazy. He’ll probably chew your head off, and it would probably be hard to keep a straight face while he’s doing it.

4. Mr. Montgomery Burns, The Simpsons

When he’s not ruling his monopoly over Springfield’s energy plant you can find him drilling for oil under the Springfield elementary school or using his office’s large suction tube to transport dissident workers to Morocco. It’s said that the former member of the Nazi party is worth 16.8 billion. With no heir apparent, no wonder Homer sticks around!

3. Michael Scott, The Office

Here’s the boss with no social filter. Scott tries to be everyone’s friend, but with comments like, “If Pam wants to show more cleavage, she should be able to,” he only manages to make his staff feel incredibly uncomfortable.

2. Bill Lumbergh, Office Space

This list would obviously be incomplete without Lumbergh. Lumbergh represents everything horrible about office jobs in particular, and every kind of job in general. His mullet-wearing, suspender-sporting, coffee mug slurping heinousness is everything we don’t want in a boss. If he’s not screwing you on the TPS reports, he’s making you work weekends — and he always knows how to get you to work weekends.

1. Darth Vader, Star Wars

Working under Darth is definitely a high-pressure job. There aren’t going to be a lot of dress casual days, and you better start learning to pass the buck, ‘cause taking responsibility for mess ups only earns you a terrifying death and, most likely, the annihilation of your entire family and/or planet.

With Darth you get “Two Strikes and the Empire Strikes Back by Choking You to Death With the Dark Side.”

Do you agree with this list? If you don’t feel free to share your own list with us!

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