People Share Their Craziest 'Michael Scott'-Esque Boss Experiences
Photo by Pablo Varela on Unsplash

We love the shows and movies that entertain us with bosses from Hell.

Working Girl. Horrible Bosses. The Devil Wears Prada. Abbott Elementary.

But the gold standard of bad bosses is Michael Scott in The Office.

That is classic. That is comedy.


People laugh at these characters to release the pain.

Redditor Supersmaaashley wanted everyone to discuss the bosses who remind them of something out of television.

So they asked:

"Do bosses like Michael Scott actually exist? And if you work/ed for one, what's your craziest story?"

Michael Scott is not a hero. He's funny. But not a hero.

He was the principal...

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"I had a boss sneak up behind a middle-aged female employee and pick her up, then immediately drop her down saying 'I didn't think you weighed that much!' He could not stop laughing. He was the principal. This occurred during passing period in a crowded middle school hallway."


$2 per time...

"I had a boss once who spent all morning locked in his office. He asked me to come in after lunch and he showed me a handmade graph. He then proceeded to explain that this was a chart of all the sex he had ever had in his life. 'See, here it is blank until I joined the army. Then I went to a sex worker here.'"

"Then they sent me to Vietnam where they only charged $2 per time. That's where you see the big jump. I was on two tours but then got shot in the face. I came back home and you see how it just drops to almost nothing. 'I was astounded.'"


between our desks...

"I had a boss that used to watch me through a gap in the glass partition between our desks. She wanted to see if I was paying attention during meetings. One day, I put a large folder to cover the gap and she freaked. I still laugh when I think about it."


So Hot!

"Never have worked for one myself, but my dad told me a story about his boss who was giving out awards to everyone in honor of how long they've worked there, and he would give speeches for each person."

"A woman employee received her award and he gave a speech about the story of how she came to work there. And he said, 'At first I didn't want to hire her because she was so hot.'"

"My dad's not working there anymore, but I love that story because I will never not picture Michael Scott giving Pam a Dundie and saying that about her."


Who said that?

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"I had a redhead boss who made us all sit down and watch a training video about how we shouldn’t refer to him as a 'ginger' because it is bullying. No one had ever called him that."


I'm having PTSD flashbacks.

I declined...

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"My a** boss insisted his daughters be flower girls in my wedding. I declined. At the reception, he told me I was spending too much time talking to one person, and I need to work the room more."



"I once worked for a family company (not my family) where my boss often had loud fights with her husband, mother, and sister (an addict with a penchant for stealing) in the halls. I have a million wonderful stories about that workplace but one that stuck out to me is this..."

"Once for someone’s birthday, she decided it would be fun to buy an anatomically correct, male blowup doll. She took this doll into the office, blew him up, and dressed him in a construction vest (the company was a contractor). When I walked by, my boss was trying to manipulate the position of the blowup penis, and asked me if I wanted to be the 'fluffer.'"



"I literally had a boss who would stop us in the middle of our work and hold company-wide meetings talking about 9/11 truther conspiracies and chemtrails. Mind you we were furniture-making company. He would get so caught up in his conspiracy theories that he forgot to order wood to make furniture one month."



"We had an anonymous feedback program at work, and our boss was livid with the results, particularly with several comments that he frequently lost his temper in meetings and would yell at us."

"The more he talked about how incorrect and unfair and hurtful these comments were, the redder and angrier he got, until he finally pounded the table and shouted, 'I DO NOT! SCREAM! IN MEETINGS! OKAY?'"


I can relate...

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"He held a meeting with our whole team less one person to discuss said person being gay. We all knew for well over a year, and never made a deal of it. So yes, they are out there and that is why the show is so funny to me. I can relate."


Michael Scott/David Brent moment...

"I believe every manager in the world has had a Michael Scott/David Brent moment; that is what makes it so hard to watch at times. I have had nights where I have often wondering how many I have had and how badly was I viewed as a result."

"My worst I think is telling someone they got a job (in a warehouse) and then realising I had told the wrong person and having to tell the him 30 minutes later that he didn't have a job after-all... dreadful."


Not Funny

"In real life it's not funny. I had a boss like that in my retail job."

"He was annoying, constantly making bad jokes, and then he ramped it up when he decided he wanted to get me to quit. For the most part I just ignored him, until he started a rumor I was hooking up with an underage coworker. Then I confronted him, and he backed off."

"Eventually he got fired for sexual harassment."



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"I had a boss once offer me $50 if I came in to cover a shift for him. Instead of paying me cash he gave me a comic he claimed was worth $50. It wasn't."



"I've never watched The Office but I had one former boss who was a bit odd. He was department head for a group of adults ranging from mid 20s to mid 60s, and in staff meetings he said on a number of occasions that he needed to go 'potty.'"

"He'd occasionally not bother doing things like managing or coordinating and instead would take on some of the tech's jobs (IT) like preparing new laptops for staff or other stuff which more often than not had to be redone from scratch because he f**ked something up."

"Occasionally on Fridays he would come to work dressed in these very poofy white long sleeve shirts as if he'd just walked off the set of Pirates of Penzance and accessorized this with a puka shell necklace."


Happy Thanksgiving!

"I used to work stocking shelves at a grocery store. Thanksgiving was coming up and we were slammed. We were getting a massive shipment in, almost twice as many pallets as we normally get. After we unload the truck, we're all scrambling to get things done so we can leave on time."

"Well our manager calls an emergency meeting. We all get into the back office and he proceeded to have a 45 min meeting about this is a big shipment and we can't waste time. I thought it was a weird joke but he thought he was giving us a pep rally."


The Worst

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"I filed a complaint about my manager with corporate over very unsafe (mentally and physically) work conditions. My boss responded by holding a meeting and telling us she could slit our throats and not feel bad about it. The worst job experiences ever and it wasn’t even a big deal job, I was a f**king maid."


week to week...

"Late to this party... I told him we were pregnant, but it was early and we weren't telling anyone (we had had a few miscarriages), so he emailed the entire agency congratulating us. After the baby my wife had a little belly. Nothing major just a Pulp Fiction 'pot.' A year or so after the baby was born he congratulated her in the parking lot on being pregnant again. We were not. His wife was there and was mortified."

"A year later he congratulated me again saying he saw my wife and when were we due. This was in front of all the ladies in the office. Again, we were not pregnant. I once made him cry bc I told him a client didn't really like him and would rather deal with me."

"He had one of those yoga balls he would sit on instead of an office chair and he would bounce up and down while taking to you. The list is exhaustive. This was at the height of the American Office popularity so it was downright amazing to see it represented so accurately on a week to week basis."



"They certainly do. That's why the show's so funny. Had a general manager give a line that sounded exactly like it came out of the mouth of Michael. He wanted to say 'be there or be square.' He started the phrase wrong, but his brain knew it was a rhyme. So he said 'be here or be queer.'"


This character is funny on screen, but a nightmare in real life.