Skip to content
Search AI Powered

Latest Stories

People Share Their Craziest 'Michael Scott'-Esque Boss Experiences

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

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.

THAT IS TOO REAL!

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...

The Breakfast Club Rockstar GIFGiphy

"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."

jezebellrae

$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.'"

Bolaixgirl_105

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."

harperv215

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."

REDDIT

Who said that?

ginger GIFGiphy

"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."

REDDIT

I'm having PTSD flashbacks.

I declined...

Staring Episode 2 GIF by The OfficeGiphy

"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."

holmen-2001

Fluffer

"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.'"

Bananabreadandchill

Fool

"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."

PAzoo42

Feedback

"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?'"

BigShoots

I can relate...

Awkward The Office GIFGiphy

"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."

lala710

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."

ell_wood

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."

moak0

$50

Pass Thumbs Down GIF by TinasheGiphy

"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."

ClioEclipsed

Fridays

"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."

DarthContinent

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."

Lefthandfury

The Worst

Angry Season 9 GIF by ShamelessGiphy

"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."

theoriginalsauce

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."

doordonotaintnotry

Michael

"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.'"

squatsquirrel

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

More from Trending/best-of-reddit

George Conway; Laura Loomer
Dimitrios Kambouris/Getty Images for CNN; Brandon Bell/Getty Images

George Conway Epically Trolls Laura Loomer After She Claims New York DMV's Credit Card Machine Displayed 'Palestinian Flag'

Conspiracy theorist and acolyte of MAGA Republican President Donald Trump Laura Loomer drew widespread ridicule over her latest outrageous claim. Lawyer and ex-husband of Trump staffer Kellyanne Conway turned anti-Trump activist George Conway lead the charge on calling Loomer out on her latest nonsense.

On October 7, Loomer shared a photo on X that was allegedly taken at a Department of Motor Vehicles office in New York City. The MAGA influencer also tagged NYC's progressive Democratic Socialist Mayor Zohran Mamdani's personal X account.

Keep ReadingShow less
Susan Collins
Tom Williams/CQ-Roll Call, Inc via Getty Images

Susan Collins Dragged After GOP PAC Boosts Her Campaign In The Wrong Portland

On July 4, 1786, the city of Portland, Maine, was officially founded with its newly-minted name. Almost 60 years later in 1845, Maineiac Francis Pettygrove won a coin toss against Asa Lovejoy and named their soon-to-be incorporated city in Oregon Portland after the largest city in his home state of Maine.

Since then, Portland, Oregon, has swelled to a city of approximately 675,000 people while its namesake boasts a population of just 70,000. In 2026, when people hear Portland, they think of Oregon instead of the original city in Maine.

Keep ReadingShow less
Screenshot of Whitey Taylor
CNN

CNN Just Visited A Struggling MAGA Store—And It Spells Bad News For Trump

CNN correspondent Elle Reeve returned to Whitey Taylor's Trump Town USA in Boones Mill, Virginia, for the first time since visiting in 2023, and her segment shows that business for the Donald Trump-themed shop has collapsed as more MAGA followers break away from the president.

Reeve, in a segment for Anderson Cooper 360, reported that "things aren't what they used to be" for the store. She spoke with Taylor, who revealed that the store, which used to make $12,000 to $15,000 in sales per day now only makes between $1,500 - $2,000 per day. On occasion, Taylor will hit $3,000 in sales if he's lucky.

Keep ReadingShow less
Pete Hegseth
Alex Wroblewski / AFP via Getty Images

Pete Hegseth Roasted After Video Of Him Trying And Failing To Keep Up With Marines Goes Viral

Defense Secretary Pete Hegseth was widely mocked after he was shown struggling to keep up with Marines while running around a track during a recent training.

In a C-SPAN video shared by FactPost on X, Hegseth is shown lagging beyond the pack as Marines jog around a track in San Diego.

Keep ReadingShow less
Vice President JD Vance speaks during a Washington, D.C., press conference on American jobs and visa fraud.
C-SPAN

JD Vance Blasted After Sharing His Absolutely Mind-Numbing Definition Of 'Socialism'

According to Merriam-Webster, socialism broadly refers to economic and political systems centered on collective or government ownership and control of the means of production.

Not exactly a concept requiring a Ph.D. to explain. One would think Vice President JD Vance, a Yale Law School graduate whose party practically uses the word as punctuation, could manage a working definition.

Keep ReadingShow less