25 Terrible Bosses That Will Make You Appreciate Your Boss This National Boss Day

25 Terrible Bosses That Will Make You Appreciate Your Boss This National Boss Day
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Do you like your job? Do you enjoy going to work every day? Does your boss treat you right? Well, if he/she does, make sure you wish him/her a Happy National Boss Day!

Bosses: even if you don’t like them, still wish them a happy day (you never know, a little brown nosing can go a long way). Today is the day we celebrate those who employ us by showing up to work on time, not talking smack about them during our lunch breaks, and actually doing work at our desk whenever they walk by.

Without our bosses, we wouldn’t have jobs, so for that we thank them. You may not love your boss, but hey, it could always be worse. Here are the 25 terrible bosses that will make you appreciate your boss this National Boss Day:

Michael Scott, “The Office”

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Though seemingly loveable at times, could you imagine having to work for him at Dunder Mifflin? He’s sarcastic, inappropriate, overly-sensitive and offensive to a point that makes him a hilarious character, but a horrible boss.


Ari Gold, “Entourage”

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I don’t think any boss in the history of television will ever compare to the wrath of Ari Gold. Poor Lloyd, so innocent.


Jacobim Mugatu, “Zoolander”

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Always be aware if your boss gets farty and bloated from a foamy latte!


Mike Jeffries, Abercrombie & Fitch

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Pretty much the biggest dickhead in the world, his comments about fat woman and unpopular kids are so cruel, it’s hard to believe this man actually exists in real life. Boo Abercrombie & Bitch!


Mr. Spacely, “The Jetsons”

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This little midget — who looked like a cross-breed between Danny Devito and Hitler — had more of a Napoleonic Complex than Napoleon himself.


Dave Harken, “Horrible Bosses”

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Isn’t that just what every employee wants to hear from his/her boss?


Gordon Gekko, “Wall Street”

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When it comes to high expectations and a complete apathy for ethics, Gordon Gekko is the king.


Dr. Julia Harris, “Horrible Bosses”

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While part of me would love nothing more than for Jennifer Aniston to make me her little bitch, it is pretty inappropriate when she’s your boss.

Bobby Pellitt, “Horrible Bosses”

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Wouldn’t you want to kill a guy who put you in these awkward types of situations?


Bill Lumbergh, “Office Space”

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Umm yea… if you never had to work for a guy like Bill Lumbergh, that would be great.


Mr. Krabs, “Spongebob Squarepants”

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Think your boss is a bit of a crab? Imagine actually working for one!


Dr. Evil, “Austin Powers”

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Who would want to work for a guy that, with one button, can send you into a pit of fire? Better off just to sit still and “zippit.”


George Steinbrenner, “Seinfeld”

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We may have only seen the back of his head, but it was enough to assure us that working for the Yankees isn’t as fun as it may seem.


Donald Trump

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Think you’ve ever been scared about getting fired now? Try working for the master of firings.


Carter Pewterschmidt, “Family Guy”

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Conservative billionaire and owner and CEO of Pewterschmidt Industires, Mr. Pewterschmidt only cares about money and making his employees miserable.


Miranda Priestly, “The Devil Wears Prada”

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This Editor-in-chief of fashion magazine Runway, Miranda Priestly puts the itch in the word bitch.


Chef Gordon Ramsay, “Hell’s Kitchen”

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When it comes to yelling, berating and insulting workers, Chef Gordon Ramsay takes the cake!


Mr. Burns, “The Simpsons”

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The ultimate evil money-loving cartoon boss, Mr. Burns has been terrorizing Homer for nearly 24 seasons.


Mr. Pitt, “Seinfeld”

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How would you feel if your boss made you spend hours picking out the perfect pair of socks for him?


Jack Donaghy, “30 Rock”

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This narcissistic, befuddling boss may be entertaining on TV, but in real life would drive any employee out of work.


Margaret Tate, “The Proposal”

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Would you want to get stuck in a fake marriage with your boss?


George Bluth, “Arrested Development”

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It’s hard to run a successful company from a jail cell. At least there’s always money in the banana stand!


Tony Soprano, “The Sopranos”

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Probably the last guy you’d want to ever cross, ever.


Walter White, “Breaking Bad”

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He will make you cook meth even if it means killing your girlfriend’s son. Now that’s a tough guy to work for!


Nookie Thompson, “Boardwalk Empire”

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Might be acceptable to drink booze on the job, but one f*ck up, and you’re dead.

Now get back to work before your boss realizes you just wasted five minutes on this article!

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Tyler Gildin

Tyler Gildin is an NYC-based Stand Up Comedian and the Creative Director at Elite Daily. He is a Television Radio Film graduate from Syracuse University and performs at clubs and colleges all over the country. He’s been written up and interviewed in publications including Newsday, CBS New York, AOL Patch and SiriusXM Mad Dog Radio. He once forgot to wear his underwear to school in 4th grade, and his mom came and brought them for him in a manila envelope. His teacher opened it in front of the class.

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